The Chicago Syndicate: John Dillinger
The Mission Impossible Backpack

Showing posts with label John Dillinger. Show all posts
Showing posts with label John Dillinger. Show all posts

Monday, November 07, 2022

The Year of Fear: Machine Gun Kelly and the Manhunt That Changed the Nation

It's 1933 and Prohibition has given rise to the American gangster--now infamous names like Bonnie and Clyde and John Dillinger. Bank robberies at gunpoint are commonplace and kidnapping for ransom is the scourge of a lawless nation. With local cops unauthorized to cross state lines in pursuit and no national police force, safety for kidnappers is just a short trip on back roads they know well from their bootlegging days.

Gangster George "Machine Gun" Kelly and his wife, Kathryn, are some of the most celebrated criminals of the Great Depression. With gin-running operations facing extinction and bank vaults with dwindling stores of cash, Kelly sets his sights on the easy-money racket of kidnapping. His target: rich oilman, Charles Urschel.

Enter J. Edgar Hoover, a desperate Justice Department bureaucrat who badly needs a successful prosecution to impress the new administration and save his job. Hoover's agents are given the sole authority to chase kidnappers across state lines and when Kelly bungles the snatch job, Hoover senses his big opportunity. What follows is a thrilling 20,000 mile chase over the back roads of Depression-era America, crossing 16 state lines, and generating headlines across America along the way--a historical mystery/thriller for the ages.

Joe Urschel's The Year of Fear is a thrilling true crime story of gangsters and lawmen and how an obscure federal bureaucrat used this now legendary kidnapping case to launch the FBI.


Wednesday, June 02, 2021

Killing the Mob: The Fight Against Organized Crime in America by the Award Winning @BillOReilly

Killing the Mob: The Fight Against Organized Crime in America, is the tenth book in Bill O'Reilly's #1 New York Times bestselling series of popular narrative histories, with sales of nearly 18 million copies worldwide, and over 320 weeks on the New York Times bestseller list.

Instant #1 New York Times, Wall Street Journal, and Publishers Weekly bestseller!

In the tenth book in the multimillion-selling Killing series, Bill O’Reilly and Martin Dugard take on their most controversial subject yet: The Mob.


O’Reilly and co-author Martin Dugard trace the brutal history of 20th Century organized crime in the United States, and expertly plumb the history of this nation’s most notorious serial robbers, conmen, murderers, and especially, mob family bosses. Covering the period from the 1930s to the 1980s, O’Reilly and Dugard trace the prohibition-busting bank robbers of the Depression Era, such as John Dillinger, Bonnie & Clyde, Pretty Boy Floyd and Baby-Face Nelson. In addition, the authors highlight the creation of the Mafia Commission, the power struggles within the “Five Families,” the growth of the FBI under J. Edgar Hoover, the mob battles to control Cuba, Las Vegas and Hollywood, as well as the personal war between the U.S. Attorney General Bobby Kennedy and legendary Teamsters boss Jimmy Hoffa.

O’Reilly and Dugard turn these legendary criminals and their true-life escapades into a read that rivals the most riveting crime novel. With Killing the Mob, their hit series is primed for its greatest success yet.


Tuesday, October 27, 2020

Second City Sinners - True Crime from Historic Chicago's Deadly Streets #BookRecommendation

Countless crimes have riveted Chicago and its surrounding communities throughout history. Second City Sinners offers front-row seats to the Haymarket Riot that exploded across the city in 1886, then bleeds through the historic back alleys, skirting past a murderous butcher, the Black Hand, Tommy O'Connor's jailbreak, and John Dillinger's final flick at the Biograph Theater. In the courtroom, witness Clarence Darrow in 1894 as he defends the man who murdered Chicago's mayor, and then again in 1924 as Darrow attempts to save the young men who tried to plot the perfect crime.

Many of the voices of these historic characters come from the journalists of their era, reporting on life and death in Chicago. Chicago Sun-Times journalist Jon Seidel takes readers back in time to the days when H. H. Holmes lurked in his "Murder Castle" and guys named Al Capone and John Dillinger ruled the underworld. Drawing upon years of reporting, and with special access to the Chicago Daily News and Chicago Sun-Times archives, Jon Seidel explains how men such as Nathan Leopold, Richard Loeb and Richard Speck tried to get away with history's most disturbing crimes.

Second City Sinners: True Crime from Historic Chicago’s Deadly Streets, is published by Lyons Press and is available in hardcover, on Kindle or Nook, or as an audiobook.


Wednesday, July 08, 2020

Chicago’s Crime Shrines

Chicago has a rich mob history, and Craig Alton capitalizes on the fascination of tourists and Chicagoans alike with his Untouchables Tour, a bus trip to some of the city's infamous gangster sites. Alton, better known by his nickname "Southside," suggests a few stops for those interested in checking out the history of Chicago's underworld.

Across from Holy Name Cathedral
Dion O'Banion, leader of the North Side gang, owned a flower shop here and was killed on the store steps in 1924 by some of Al Capone's men after he allegedly double-crossed Capone's mentor, Johnny Torrio. The shop is no longer there.

Green Mill in Uptown
A favorite hangout of Al Capone and his gang. Capone would sit at a table with a view of both doors. The club, which was connected by a tunnel system to a building across the street, still has a trap door behind the bar.

Site of Valentine's Day Massacre

The murders occurred on Feb. 14, 1929, at a garage at 2122 N. Clark St., where Capone's men, dressed as police officers, tried to set up George "Bugs" Moran, then the head of the North Side gang. Seven of Moran's men were gunned down, but Moran wasn't in the garage at the time. The building is no longer there.

The Biograph Theater
John Dillinger, named the FBI's "Public Enemy No. 1," was set up in 1934 by a woman who told the feds he'd be at the movies with her. When Dillinger walked out of the theater, located at 2433 N. Lincoln Ave., he was shot in the alley.

Al Capone's grave
Al Capone was buried at Mt. Carmel Cemetery, 1400 S. Wolf Rd. in Hillside.

More sites listed on the Chicago Mob Infamous Location Map.


Thursday, December 05, 2019

Nephew of John Dillinger, Who Planned Documentary on The History Channel, Has Lawsuit against Cemetery Dismissed

A nephew of 1930s gangster John Dillinger needs a cemetery's permission to exhume the notorious criminal's Indianapolis gravesite to prove whether he's actually buried there
, a judge ruled Wednesday in dismissing the nephew's lawsuit against the cemetery.

Marion County Superior Court Judge Timothy Oakes granted Crown Hill Cemetery's motion to dismiss Michael Thompson's lawsuit, saying Indiana law requires the cemetery's consent.

“The limited question before the Court today is whether disinterment may occur under this section of the statute without cemetery approval. Court finds that the statutory requirements for this section of the statute are clear in that disinterment requires the cemetery owner to give consent before disinterment may occur," Oakes wrote. He added that Indiana law “does not require that the cemetery have a valid, rational, or meaningful reason" for withholding its consent.

Thompson sued the cemetery in August after it objected to his plans to exhume the grave as part of a television documentary. Thompson has said he has evidence Dillinger's body may not be buried there, and that he may not have been the man FBI agents fatally shot outside a Chicago theater on July 22, 1934. The History Channel dropped out of the planned documentary in September.

Attorneys for Crown Hill Cemetery call that “a decades-old conspiracy theory.” They opposed the exhumation, saying in court documents that Indiana’s Legislature has granted cemetery owners the right to “protect its gravesites from unwarranted disturbance.”

Alice McKenzie Morical, an attorney for Crown Hill Cemetery’s management company, said during Wednesday’s hearing that there was an autopsy after Dillinger’s fatal shooting and relatives identified him before his burial. “His close family believed it was him and they wanted him in the family plot,” she said.

The cemetery's management company said in a statement that it’s pleased with Wednesday's ruling and it “continues to object to the disinterment of John Dillinger.”

The FBI insists it's a "myth" that its agents didn't kill Dillinger and that "a wealth of information supports Dillinger's demise," including fingerprint matches.

Thompson obtained an Indiana State Department of Health permit in October that calls for the remains to be exhumed on Dec. 31.

Thompson’s attorney, Andrea Simmons, told the court that her client obtained a large number of FBI files that raise serious questions about whether it is Dillinger's body buried at the hilltop cemetery. “There is strong reason to believe that he’s not the person in the grave," she said.

Oakes said Wednesday that he questioned the cemetery’s contention that the exhumation would be disruptive. “I don’t buy into the cemetery’s reasons, but under the statute they don’t have to have a reason that is rational,” he said.

Oakes dismissed the lawsuit without prejudice. Under Indiana law, Thompson’s attorney have 10 days to file an amended complaint citing a different section of Indiana’s law governing exhumations or 30 days to appeal the decision to a higher court. “It may be several weeks before a final decision is made what to do next,” Simmons said in a statement.

A few days after his 1934 burial, Dillinger's father had his casket covered with a protective cap of concrete and scrap iron topped by four reinforced-concrete slabs to prevent vandals from trying to dig him up, according to Susan Sutton, a historian with the Indiana Historical Society.

Some surviving family members still object to Thompson's plan.

Dillinger's great-great niece, Stephanie Samuels, said after Wednesday's hearing that she and other relatives planned to file a formal complaint objecting to any exhumation. “This should never have gotten this far. I think it’s very disgraceful to the family, everything to do with it,” she said. “And there is very much family against this."


Wednesday, September 06, 2017

Examining the Crimes of the Calabrese Family #FamilySecrets

Why are we so fascinated by the mob? Well, there's violence: garroting, shooting, stabbing; the thrill of men hunting men. Money: While most of us sweat for our daily bread, gangsters take what they want. The unknown: Gangster stories give us special knowledge of dark, hidden places in the city and in the human heart.

That last point is important, because half the fun is pulling back the veil. The author strips away the pretenses and pleasantries of daily life and reveals how the world really is. Which is to say that force reigns supreme, not intelligence or character or merit. But part of the popularity of gangster lit is the assumption that the veil is only ever half-raised. Mob stories feed our most paranoid fears by implying that so much more remains to be told. Because we really can't see the subject whole, never know the limits of the mob's influence, we can imagine it as all-powerful, with cops, politicians and businessmen bought and paid for. Authors let us in on the secrets, but the thrilling question always remains, just how big is this menace?

That is one of the reasons that Chicago Tribune reporter Jeff Coen's "Family Secrets: The Case That Crippled the Chicago Mob" is so refreshing. He never reaches beyond his story, sticks close to his evidence, lets the carefully gathered wiretaps and eyewitness testimony and reporter's notes do the talking. Like Nicholas Pileggi's classic "Wiseguy," on which the film "GoodFellas" was based, Coen keeps it at street level, focusing on his distinct cast of characters, the gangsters and their victims, the federal agents, local cops and attorneys who played out the drama.

During the 1970s, '80s, and '90s, Frank Calabrese Sr. operated a lucrative loan-sharking business on Chicago's South Side. He had ties to higher-ups in the "Outfit," as the Chicago mob is known, men like Joey "the Clown" Lombardo, and James "Jimmy Light" Marcello. Calabrese was not a nice man. In the late '90s, his son, Frank Jr., musing on his father's abusiveness, decided to turn state's evidence against the old man. Seeing the handwriting on the wall, young Frank's uncle Nick (Frank Sr.'s brother) also decided to cooperate with the feds.

With that the Outfit's cover unraveled, and the case finally came to trial in 2007. Coen gives us fine-grained pictures of the loan-sharking and extortion, and, above all, at least 18 killings.

Nick Calabrese, a reluctant hit man, committed multiple murders at brother Frank's behest. Nick told the feds that his sibling would willingly kill him had he failed to carry out a hit. Frank Calabrese himself specialized in garroting his victims, then cutting their throats to make sure they were dead. Coen gives us gruesome accounts of the murders and burials in corn fields and at construction sites.

"Family Secrets" isn't for everyone. It is a complex narrative of a long case that resulted in several convictions. The devil is in the details, there are a lot of them, and they thoroughly de-romanticize the mob.

This is a well-written and researched book, but its subject might disappoint some readers. Unlike the East Coast mob, Coen tells us, "Chicago had been unified for much of the century, since the days of the infamous boss Al Capone. ..." That statement is true but a bit deceptive. This late 20th Century crew seems a little pathetic. They're not exactly the gang that couldn't shoot straight, but they're certainly not Capone's Outfit either. When we pull back the veil, we get a strange blend of Don Corleone and the Three Stooges.

Thanks to Elliott Gorn, who teaches history at Brown University. He is author of "Dillinger's Wild Ride: The Year That Made America's Public Enemy Number One," published this year by Oxford University Press.

Sunday, June 25, 2017

Al Capone's Diamond Pocket Watch Sold for Over $84K at Gangsters, Outlaws & Lawmen Auction

Al Capone's diamond-studded, platinum pocket watch went for $84,375 during an auction Saturday featuring other artifacts that belonged to some of America's most notorious gangsters.

Al Capone Diamond Pocket Watch


Capone's watch as well as a musical composition he handwrote behind bars in Alcatraz were among the items up for bid in the "Gangsters, Outlaws and Lawmen" auction by RR Auction, an auction house headquartered in Boston. The auction was held Saturday afternoon at the Royal Sonesta hotel in Cambridge, Massachusetts.

Capone, who was born to Italian immigrants in New York City, headed a Chicago-based crime empire during the Prohibition era that raked in millions of dollars through bootlegging, gambling, racketeering and other illicit activities. He was dubbed Scarface by the press after his face was slashed during a fight, a nickname he apparently disliked.

"Unlike his more maligned moniker of ‘Scarface,’ Capone preferred that those closest to him call him by ‘Snorky,’ a slang term which meant ‘sharp’ or ‘well-dressed,'" according to a description accompanying Capone's watch on RR Auction's website.

According to the auction house, the rounded triangular pocket watch was personally owned and used by Capone. The timepiece is on its original chain made of 14-karat white gold. The exterior of the case features 23 diamonds shaped to form Capone's initials, "AC," which are encircled by 26 additional diamonds. Another 72 diamonds circle the watch's platinum face and gold-tone impressed numerals.

Online bids for Capone's watch had surpassed $17,000 prior to the live auction Saturday afternoon. Experts estimated the item would sell for more than $25,000, according to RR Auction.

A musical piece entitled "Humoresque," written in pencil by Capone when he was incarcerated in Alcatraz in the 1930s, was also up for grabs. The musical manuscript shows Capone's softer side, containing the lines: "You thrill and fill this heart of mine, with gladness like a soothing symphony, over the air, you gently float, and in my soul, you strike a note."

Experts estimated the sheet will sell for over $20,000, according to RR auction. it went for $18,750.

Also up for auction was a letter written by gangster boss John Gotti, two life-size death masks of gangster John Dillinger, a brick from the scene of the 1929 St. Valentine’s Day Massacre, and jewelry that belonged to infamous crime duo Bonnie and Clyde.

Thanks to Morgan Winsor.

Monday, May 08, 2017

All Against The Law: The Criminal Activities of the Depression Era Bank Robbers, Mafia, FBI, Politicians, & Cops

This book tells the remarkable true stories of America’s most infamous Public-Enemy-Number-1 gangsters. Based on exhaustive documented research, Bill Friedman chronicles the true history of illegal gambling, rum-running, organized crime, and the politics of law enforcement during the Prohibition era.

Based on crime-scene eyewitness accounts, state’s witnesses harborers’ accounts, and historical records, Friedman paints exciting portraits of John Dillinger, Pretty Boy Floyd, Baby Face Nelson and other luminaries of the underworld—and documents how surprisingly different that world was from the way Hollywood portrays it. Like great literary characters, history’s gangsters and bank robbers were complex and fraught with contradiction.

Captivating tales of criminal daring are balanced with shocking political exposés revealing how complicity and incompetence hindered the effectiveness of law enforcement. Written in fast-moving prose that’s sure to entertain, All Against The Law: The Criminal Activities of the Depression Era Bank Robbers, Mafia, FBI, Politicians, & Cops, is a must-read for anyone who loves classic American ‘cops and robbers’ stories. Friedman’s historical accounts are as exciting and dramatic as any genre fiction, while ringing with the power of truth and authenticity.

All Against The Law: The Criminal Activities of the Depression Era Bank Robbers, Mafia, FBI, Politicians, & Cops” covers U.S. major crime in the Great Depression era. It is the incredible stories of daring prison escapes and breathtaking police pursuits by the Great Depression’s four successive Public Enemies Number One - John Dillinger, Baby Face Nelson, Pretty Boy Floyd, and Alvin Karpis with the Barker brothers. These were the most aggressive and dangerous killers ever. When fleeing from pursuing lawmen, every one of these bank robbers either whirled their cars around and floored their accelerator towards their pursuers, or they ran in the open, charging pursuers while relentlessly blasting away with machineguns. All these ferocious counterattacks made them dreadfully successful at killing the most policemen and FBI agents of any American outlaws. This is the first complete history because the newspaper accounts and trial testimonies by both their criminal cohorts and the harborers during their long fugitive manhunts are included.

Against these fierce killers, Congress assigned a fledgling Federal Bureau of Investigation (FBI), an accounting agency of government money made up of politically-appointed accountants and attorneys with no police experience. Headed by J. Edgar Hoover, a librarian, he failed to teach his agents any of the fundamentals of police and detective work or instruct them to respect individual liberties and rights. Thus, his courageous but ill-prepared early agents conducted one amateurish and failed raid after another that occasionally caused disastrous results for both his agents and innocent civilian bystanders caught up in the lines of fire.

Hoover’s leadership and management of the FBI has been thoroughly discredited by contemporary exposé articles and scholarly historical biographies. This book penetrates the veil much further in presenting how politically-conservative Hoover failed to prosecute serious criminals, used underhanded illegal tactics against critics; occasionally fought to survive his malfeasance in office; and blackmailed errant Congressmen to further his own political agenda. All this made him an unaccountable malevolent fourth branch of the federal government totally outside the brilliantly-conceived Constitutional checks-and-balances system.

To disprove that the FBI’s chief suspect, Pretty Boy Floyd, was involved in the Kansas City Massacre that slaughtered four lawmen, and to finally reveal the actual perpetrators and their motives, the forty-year reign of that town’s unique political-power structure is laid bare. The town’s political kingmaker Jim Pendergast chose as his lieutenant the city’s Mafia leader, and this Mafioso selected the chief of police and his detectives. The state legislature tried to stop this affront to justice by having the governor appoint a Police Commission to control the city’s departmental hirings. This action just led Kansas City’s Mafia chieftain to expand his political sphere of influence across the state to elect puppet governors who appointed Commissioners of his choosing.

These Kansas City political leaders stuffed ballot boxes in every election of politically-progressive Harry Truman, who later became the only president to sell out to organized crime because of his long political ties to the Kansas City Mafia. The entire last chapter strictly covers the many interactions Truman had from the White House with this Mafioso. Their mutual political hijinks, conflicts, and intrigue are astonishing. As tensions mounted this Mafioso was murdered, and Republican leaders in the U.S. Congress directly accused the President of ordering his political henchmen to kill him. This whole period in the White House is beyond mind-boggling.

A number of the gangsters in this book had ties to the early Nevada gambling industry, where the author spent his whole career. The action opens in that state, when Reno was its largest city, and Bill Graham and Jim McKay were the biggest casino operators both before and after gambling was legalized in 1931. Prior to Baby Face Nelson going into bank robbing, he was their doorman/bouncer. Graham and McKay operated the most popular casino in the state’s largest hotel, the Golden, and they developed an effective but very illegal tourist-marketing program to bring in high-rollers during the Great Depression. They offered an emporium of services for criminals who stole money through armed robbery, kidnapping, or by con. This drew financial criminals in large numbers from across the country. One service was to hide fugitives on the run in this isolated town and protect them from police interference. In the weeks to months before the FBI took down Dillinger, Nelson, Floyd, Karpis, and Fred Barker, all enjoyed the safe haven provided by Reno’s casino operators.

Before Ben Siegel began construction of his Fabulous Flamingo gambling resort, Kansas City Mafioso Charles Binaggio, who was shot to death under President Truman’s portrait, had planned to become a major investor in the Thunderbird Hotel & Casino on the Strip. A number of other links between the Kansas City Mafia and the Nevada casino industry during this era are presented. This book closes with the career of Kansas City’s fifth Mafia leader, Nick Civella. As the original pioneer gangsters, who had built the Las Vegas Strip from their Prohibition fortunes, retired and sold out, Civella financed a new wave of hidden underworld casino owners through the Teamsters Union Pension Fund, as was fictionally presented in the 1995 movie Casino.

This book is based on 47 years of research, and it has an enormous amount of new information. It details the major crimes of that era, and it exposes major corruption by politicians, police detectives, prosecutors, and judges. Justice eventually prevailed as the vast majority were imprisoned.

Every word comes from the victims, eyewitnesses, local police officials, or the pursuing FBI agents' official internal reports, as documented in 34 pages of 326 endnotes. the subject Index is 14-pages of double-columns.

Thursday, April 06, 2017

How Did Chicago became a Cultural Capital of Crime?

The thing outsiders know about Chicago is crime. The mobsters, the street drug gangs, the corrupt operators—these are the most sensationalized aspects of the city. But they are also key factors in its ongoing narrative, the one true Great American Novel that is Chicago. The city with a fiery creation myth grew into a blue-collar metropolis with the help of oily, feudal political machines and assorted local species of crook, leaving a deep, ugly legacy. It is written in our street grid, our transit lines, and our segregated accents, in which one can still hear both the old white ethnic strongholds and the Great Migration. It can be a very beautiful city, especially at night. In those icy parts of winter that have become more rare since I first moved here, the unique nighttime color of Chicago reflects in every direction. The flatness of the landscape and the straightness of the streets bring its divisions into deep focus. I’m proud to show it off. It is a city on the prairie, and therefore a city of the plain, like Sodom and Gomorrah in Genesis.

For a time in the 1850s, there were so many problems with drainage that it became a swamp and had to raise itself up on jackscrews. So really, a Chicagoan has their pick of origin stories. The curse of the so-called Second City is that it lends itself effortlessly to symbolism and especially to metaphor, to the point that you start to believe that it just might be one. I’ve lived here longer now than I have anywhere else, and I have come to love this aspect of the city. When Chicagoans speak—whether they are true locals or transplants like myself, who have come to its ways through prolonged exposure—they speak its complicated history. This is the diverse Southern-inflected sound of black Chicago, the “Chi-cah-go” and “Chi-caw-go” pronunciations that classify white accents, and that perfect formulation of terse Midwesternese, the stranded “with,” as in the classic “You wanna come with?” They say “jagoff” is a Pittsburgh word, but Chicago owns it.

Really, there are many Chicagos, bound almost psychically. It is better maybe to try to grasp it in terms of its architecture—which is really one of the most beautiful things about it—and planning. For instance, Chicago is the alley capital of the world. There are about 1,900 miles of alleyways running through almost every block of the city, regulated to a minimum width of 16 feet, some much wider. The alley is part of day-to-day life in Chicago: It’s where we take our shortcuts and bring our trash. It’s why Chicago doesn’t smell as bad as other big cities. It lacks that note of garbage that gives New York streets their character. The kind of buildings we call two- or three-flats, whether brick, frame, or Indiana limestone (called “greystone” locally), will often have a gangway, a passage that lets you cut from the sidewalk to the alley. My favorites are the ones that dip under a protruding oriel. And most of the apartments in those two- and three-flats will have two doors, one in the front and one in the rear. It’s a city of backstreets and backdoors.

Chicago crime is a unique phenomenon. In broad statistics, it is not that dangerous a place; the rates of burglary and theft are low for an American city, and many of its neighborhoods experience negligible violent crime. This is a common defense tactic for Chicagoans, especially white Chicagoans—the “well, not my Chicago” plea. But this is as much a fantasy as the Trumpian burning of the quote-unquote “inner city.” Chicago crime inspires fascination because it is entrenched and so specific, so troublingly connected to a diverse city that otherwise eludes broad social generalizations. One fact about Chicago is that it has more nicknames in common circulation than any other place in this country, all of them kind of tacky: the Windy City, the Second City, Chi-Town and its pun variations, the City Of Big Shoulders. There are many others, too. Defining the spirit of Chicago is a bad parlor game. The nice parts of it are very nice, but for more than 90 years, it has been world-famous as a place where people get gunned down in the street. Throughout its history runs a succession of criminal boom industries: gambling, policy, liquor, crack, heroin.

The criminal conglomerates of Prohibition and the small sets of the West Side’s Heroin Highway are part of one uninterrupted story, though unwittingly. The story is the city. It goes back to the 1870s and the reign of “Big Mike” McDonald as the king of Chicago’s gambling underworld. It goes through generations of increasingly more effective political machines and increasingly larger criminal syndicates, colluding in political and commercial networks that made the street gangs seem like the inevitable result of a complicated equation. Let us assume a few things here as starting points: that the city and its underworlds have existed for a long time in a relationship that is more complex than host and parasite; that political and criminal groups in the city, however big or small, play variations on a similar game involving the flow and direction of movement; and that the city is itself a crossroads, its entire story defined by lines of interstate transit, be it the Illinois Central Railroad that transported half a million black job-seekers from the South during the Great Migration, or the Sinaloa Cartel network from which most of the cocaine and heroin of its current drug economy is believed to originate.

For Chicago, there is no artistic or cultural history without its social history, no social history without its political history, and no political history without crime. The mob is a staple of our tourist kitsch industry: the Al Capone T-shirt and the Untouchables bus tour, right up there with Mike Ditka’s hairspray, the goddamn Blues Brothers, and that casserole we call a deep-dish pizza. But the mob was always corny, even at its scariest. For decades, it was almost everywhere. I’ll give you an example: The Russian bathhouse immortalized by Saul Bellow in Humboldt’s Gift was actually a mob hangout. It was still owned by an Outfit family in the years that I lived across from it on Division Street, one of the more darkly perfect street names in Chicago.

Michael Mann’s 1981 debut feature, Thief (Special Director's Edition), is to my mind the best Chicago crime film set after Prohibition and one of the great artistic interpretations of the city’s nocturnal character. It was made in the last years that Chicago nights glowed bluish-green, before the city had completed the changeover from mercury vapor lighting to the sodium vapor lamps that produce its present honey-bronze haze. Much as alleyways have both a practical and a mystical relationship to the city’s networks of crime, so it is possible to chart eras of criminality through the history of its public lighting. Crime is a largely nocturnal activity, after all, as are most of the vices on which the city’s criminal syndicates were built. In the Prohibition and Great Depression golden age of Chicago crime, most of the streets were still gas-lit and very dim. This was the fabled era of the Tommy Gun mobsters, but also of the bank-robbing outlaw, embodied by the Chicago-based Dillinger Gang, the subject of Mann’s underappreciated crime epic Public Enemies. Mercury vapor arrived in the mid-1950s, along with Richard J. Daley’s Democratic political machine and the solidification of the Chicago Outfit, the white mob, which in those years finally murdered and intimidated its way into the territory of the city’s forgotten black crime syndicates. The most recognizable type of streetlight in Chicago was introduced in this era. It’s a bucket-shaped design unique to the city, called the General Electric Crimefighter.

Thief is not a film about the Outfit, but it features an Outfit operative as a character, played by the avuncular stage veteran Robert Prosky. You have probably seen a picture of Al Capone. Chances are it’s the glamour shot with his head turned and the cigar stuffed in his cheek and the size 6 7/8 cream-white Borsalino on his little head. This is the most flattering picture of Capone. As a young man, he had the pudgy face and baggy eyes of a fortysomething bank manager. He was 26 when he inherited Johnny Torrio’s criminal empire and was out of power by the age of 33. But in movies and TV, he is always played by older actors, trimmer or more barrel-chested, always tougher-looking than the real man: Rod Steiger in Al Capone; Neville Brand, Robert De Niro, and William Forsythe in successive versions of The Untouchables; Jason Robards in The St. Valentine’s Day Massacre; Stephen Graham on Boardwalk Empire. But there were never any handsome gangsters. They were all funny-looking, and with the exception of the flashy Capone years, they dressed like shit.

The Outfit was the successor to Capone’s organization, and in that era of mercury vapor lighting, when the tint of the night suggested an extended twilight, their look was Sansabelt, grandpa glasses, and starched short sleeves. Mann grew up in the long-gone Jewish quarter of the Humboldt Park neighborhood, as did Saul Bellow a generation earlier, and he is one of the few to try to capture this banal, used-car-salesman aspect of the Chicago mob. To me, he is one of the geniuses of the genre; in all of his crime films, there is a complex dialogue between authenticity and archetype. His favorite type of verisimilitude is the kind that directly contradicts expectations. In Thief, for instance, the safe-cracker played by James Caan—the first of the single-minded professionals that would become Mann’s contribution to the mythology of the crime genre—doesn’t press the resonator of a stethoscope against a door and listen to the tumblers; he uses an industrial oxygen lance, lent to Mann by an actual Chicago-area burglar. And while Prosky’s role might seem like a case of casting against type, if you look at pictures of Outfit bosses from the time, that’s what they all looked like.But here’s the thing: The imagery Mann subverts with this more realistic portrayal—and uses to formulate his own mythology—is also Chicagoan in origin. It was Chicago that birthed both the gangster picture and the notion of street criminal chic, and it really took until The Godfather for there to be a major American film that took its cues from the clannish organized crime culture of the East Coast. Even the great New York gangster movies that came before The Godfather, like Raoul Walsh’s The Roaring Twenties and Budd Boetticher’s The Rise And Fall Of Legs Diamond, are based on an archetype born of the Second City. Most film historians will tell you that there are two definitive early gangster films: Underworld, directed in 1927 by Josef Von Sternberg, and Howard Hawks’ insurmountable 1932 Scarface. Both are set in Chicago, as were almost all early American gangster movies—Little Caesar, The Public Enemy, the whole lot. The gritty city stuck in the imagination of ’30s Hollywood much in the same way as Paris and Vienna did, less a real-world setting than a genre in and of itself. Films about criminal gangs go back to the early 1900s, but they depict their bad guys mostly as ragged, unshaven goons in flat caps. The seductive criminals of the silent era are swindlers and masterminds. The idea that coarse, murderous thugs could be flamboyant, magnetic, and sexy—that comes from the Chicago of Al Capone and John Dillinger.

Both Underworld and Scarface were based on stories by Ben Hecht, though the latter was nominally adapted from a forgotten pulp novel of the time. Before he became one of the greatest screenwriters in the history of Hollywood, Hecht was a Chicago Daily News crime reporter, an experience he would draw on many times—most famously in The Front Page, one of several collaborations with his crime-desk colleague Charles MacArthur, subsequently reworked as His Girl Friday. Hecht was one of a number of literary men who worked in the Chicago dailies of the 1920s (the poet Carl Sandburg was also at the Chicago Daily News at the time), and the best of a tradition of newspapermen who treated the job of columnist as though it made them prose-poet laureate of Chicago. A reader of modernist and symbolist literature, he was also involved in the Little Review, the Chicago literary magazine famous as the first publisher of James Joyce’s Ulysses, which was originally serialized over several years in its pages. In Underworld, released at a time when Joyce’s landmark novel was still banned as obscene in the United States, there is a villainous Irish gangster named Buck Mulligan, after the central character of the first chapter of Ulysses—a fact that I’ve always found amusing.

The classic, Hecht-ian gangster drew on the public’s morbid fascination with Chicago crime to create something almost modernist—this wanton criminal as an epic figure in an expressively metaphorical cityscape. This is true of Scarface, a masterpiece that was the work of a number of remarkable talents, not just Hawks and Hecht. One of the many memorable things about Scarface is the use of signage as commentary and ironic counterpoint: the famous “The World Is Yours” travel ad (carried over in Brian De Palma’s loose 1983 remake); the body lying under the crossed shadow of a signboard that reads “Undertakers”; the lit-up marquee of the club called “Paradise No. 2.” The Godfather would refashion the gangster as a creature of family and loyalty, but in his original conception, he was a creature of the city. Scarface’s Capone-inspired title character doesn’t rise to power in the middle of nowhere, but in a darkly comic metropolis that seems to empower and mock him in equal measure. In other words, he rises to power in Chicago.

It should be pointed out that almost all Chicago-set Hollywood films produced from the late 1920s to the 1970s are about mobsters, crime, or corruption. We’re talking Nicholas Ray’s Party Girl, assorted half-remembered noirs, various versions of the Roxie Hart story (including one written by Ben Hecht), the premise of Some Like It Hot. Of these, only Arthur Penn’s Mickey One, the film that first attempted to apply a French New Wave sensibility to home-grown pulp, did any substantial filming here, capturing both its decrepit alleys and its modernist architecture in stark black-and-white. It was only in the 1980s that the city became a popular filming location. Perhaps Thief seems definitive because it represents a point of merger—between the mythology of the city and its reality, which already seems fairly stylized.


The great musical legacy of Chicago is the modernization and urbanization of the blues, a rural sound that was electrified by the city and laid the groundwork for most popular music that has come since. One important but underappreciated figure in its development was Kokomo Arnold, who played a rapid bottleneck-slide-guitar blues in a style that still sounds rock ’n’ roll. It is said that he came to Chicago as a bootlegger in the 1920s, but was forced to rely on his musical talents for a living after the end of Prohibition, trading one business of handling bottles for another. However, when it comes to stories about bluesmen, one can never be sure. Arnold’s recording of “Old Original Kokomo Blues” was reworked by the Delta bluesman Robert Johnson into “Sweet Home Chicago,” now the de facto anthem of the city. “Sweet Home Chicago” isn’t actually about Chicago. It uses the name of the city figuratively. It has to be the most singable place name in American English: Chi-ca-go, those three syllables, each ending in a different vowel sound. It lends itself to varied interpretation.

More so than any place in America and perhaps even the world, Chicago was founded on the idea of a city; before it had developed a cultural life of its own, it was a word, a notion, and a destination, ballooning over the second half of the 19th century from a smallish midland settlement into what was then the fifth largest city in the world. It is a place that inspires ideals—from the Wobblies to the aesthetic of Afrofuturism, the Hull House to the tradition of philosophizing architects embodied by Louis Sullivan, Daniel Burnham, and Frank Lloyd Wright. But how much of Chicago’s idealistic streak is a reaction to its cynical pragmatism? For as long as it has deserved to be called a city, Chicago has had problems with disenfranchisement, corruption, and crime—problems that seem like they were almost designed into the city. I’ll point out here that in his Whitman-esque poem “Chicago,” which is the source of the nickname “the City Of Big Shoulders,” Carl Sandburg also writes: “Yes, it is true I have seen the gunman kill and go free to kill again.” And this is the definitive celebration of the city.

It was Nelson Algren who mastered the art of making Chicago’s seediness sound like an exotic quality. He is best known for his novel The Man With The Golden Arm, which is set on that same mythologized stretch of Division Street that was home to Saul Bellow’s Russian bathhouse. Here, I’ll point out that Otto Preminger’s well-known 1955 film adaptation, starring Frank Sinatra as a heroin-addicted jazz drummer, was co-written by an uncredited Hecht, because everything somehow intersects in the novel of Chicago. It opens with a prowling long take down an evocative soundstage street that bears only a faint resemblance to the real city. It’s a Chicago of the imagination, but so are most. In his essay “Chicago: City On The Make,” published two years after The Man With The Golden Arm, Algren gave the city one of its most famous panegyrics: “Like loving a woman with a broken nose, you may well find lovelier lovelies. But never a lovely so real.” Like so many Chicago transplants who came here in the mid-2000s to lead a quasi-bohemian existence, I have this passage memorized. But it did not occur to me until many years later to ask who broke the woman’s nose.
Iceberg Slim on the cover of his 1976 spoken-word album, Reflections.

The fact is that, while the crime and corruption provide links between Chicago’s countless neighborhoods, their effects have always been graded by skin color. I know of no black writer of the same periods who wrote of Chicago crime as a sign of its resilient spirit, as Sandburg did, or as an Algren-esque existential quality, the proof of its hustle—not even Iceberg Slim, who was second only to Ben Hecht in developing and popularizing the mythology of the street criminal. Slim—who was born Robert Maupin, but took Robert Beck as his legal name in middle age—had been a dapper pimp in the black underworld of Chicago and the upper Midwest in the 1940s and 1950s, until a breakdown in the Cook County Jail led him to retire. He had been known as Cavanaugh Slim. It was while working as an exterminator in Los Angeles that he wrote his autobiographical novel Pimp: The Story Of My Life, a bestseller that would come to define the voice of gritty urban pulp. Along with his subsequent crime novels and the follow-up memoir The Naked Soul Of Iceberg Slim: Robert Beck’s Real Story, it would exert a profound aesthetic and thematic influence on gangsta rap, blaxploitation films and black variations on noir (Bill Duke’s Deep Cover, for example), and the prose of a vast array of fiction writers, most notably Donald Goines and Irvine Welsh.

Slim was a complicated figure. Like Chester Himes, the godfather of black noir, and Ed Jones, the most powerful black kingpin of Slim’s early years in Chicago, he had a go at a respectable college education before lapsing into crime—though, admittedly, he already had a lengthy rap sheet by the time he arrived at Tuskegee, where he was a student around the same time as Ralph Ellison. As a prose writer, he was ecstatic and contradictory, the king of mixed metaphors, capable of lucidly deconstructing the misogyny and self-loathing of his criminal past one moment and juicing readers with lurid sexual exploits the next. Like Hecht, he sculpted the seductive aspect of Chicago crime—but in place of the classic gangster film’s anti-social pizzazz, what he presented was a cool, toughened nihilism. Perhaps Slim came to believe his own legend. After he found recognition as a writer, he adopted the public image of a wocka-wocka mid-1970s pimp, though his own heyday had been in the days of boogie-woogie and parted hair.

Indulge me now and take a moment to listen to “County Jail Blues,” a 1941 B-side by the Chicago blues pianist Big Maceo Merriweather. It’s an ageless song, and, in my opinion, one of the great overlooked blues recordings of the 1940s. The guitarist is Tampa Red, who played a gold-plated steel-body guitar that sounds remarkably like an electric. In its ideal form, blues is not glamorous music.

The cultural legacy of Chicago crime is really two stories, but they are intertwined. The first is a story of myths, plucked from the streets and alleys of the city and fermented in the popular imagination. The second is a complex narrative of devil’s bargains between art, business, political machinery, and crime. It stretches from the brothels of the early 20th century to the super-sized media conglomerates of the present day. Let me relate one small part of it.

The first black millionaires in America were probably policy kings, most likely in that densely populated area of the South Side that was then known as the Black Belt. Policy was an illegal lottery in which winning numbers were drawn from policy wheels (often rigged), which in Chicago bore such names as the Airplane, the Kentucky Derby, and the Prince Albert. It was a huge enterprise, with each wheel having its own drops, runners, and policy writers—not to mention a whole sub-industry of numerologists and hucksters who called themselves “policy professors” and hawked dream-based winning formulae in the ad pages of the Chicago Defender. If you want to try to get a sense of the spirit of the time, take a listen to “Four Eleven Forty-Four,” by Papa Charlie Jackson, the sardonic, banjo-playing chronicler of life in Chicago’s black neighborhoods in the 1920s and the first commercially successful self-accompanied blues musician; the title is the prototypical number combination, or gig, and a byword for policy itself.

The great policy kings are mostly forgotten now: Policy Sam, Mushmouth Johnson, Teenan Jones, Ed Jones (no relation) and his brothers, Dan Jackson, Teddy Roe. But their influence on the economic and political life of the city can’t be overstated. For the first half of the 20th century, the white powers that be considered them essential to the black vote in Chicago. When it comes to this city’s history, one should probably always think cynically and feudally: a community where the largest local employer, voter registration effort, charity, and source of capital is a single criminal racket is a corrupt administrator’s dream. Political machines gave policy kings leeway to keep them in power. During their reign, the center of black nightlife in Chicago was a section of the Bronzeville neighborhood known as “The Stroll.” How perfect is that, in a city where control is synonymous with directing movement?

The 1920s and ’30s were Chicago’s heyday as a center of jazz talent and innovation. One of the most important clubs of this era was the Grand Terrace, known in its early years as the Sunset Cafe. The building—originally a garage, and until recently a hardware store—still stands on 35th Street. This was where Louis Armstrong became a star with a teenage Cab Calloway as his master of ceremonies, where Nat King Cole got his first break, and where the trailblazing pianist and bandleader Earl “Fatha” Hines had his 12-year residency, playing a piano bought for him by Al Capone. In the ’30s, the Grand Terrace had its own national radio show, broadcast live every night. Policy kings owned many popular clubs on The Stroll, including Palm Tavern (owned by Genial Jim Knight) and the Elite No. 2 (owned by Teenan Jones), which I’m almost certain inspired the similarly comical name of Scarface’s Paradise No. 2. But the most lucrative and glamorous spots were integrated black-and-tan clubs like the Grand Terrace and the Plantation, which was located across the street. Both were controlled by the Capone organization through Jewish associates.


Unlike the Outfit that succeeded him, Capone made a point of leaving the black syndicates alone. There were many reasons for this, including the fact that the mob and the policy kings were both colluding with the Republican political machine headed by Mayor William H. Thompson, a flagrantly corrupt figure who believed that the one true enemy of America was the British crown. But the one that matters here is the mob’s intended audience. The Grand Terrace attracted many wealthy black customers, from bona fide celebrities to local crime lords (Icerberg Slim’s mentor, “Baby” Bell, spent there lavishly), but it was designed to draw in white money. Anyone who wanted to make a career in Chicago had to play the mob’s segregated circuit. The white jazzmen (including such talents-in-training as Gene Krupa and Benny Goodman) mostly played whites-only venues, while the black jazzmen played black-and-tan clubs, where white musicians could sit and play if they wanted. The privilege did not go the other way around.

Thus, the mob invisibly controlled the direction of musical influence, as it did so many other things that may seem intangible. Its monopoly on early Chicago jazz had many consequences, one of which was an eventual exodus of talent, beginning with the great cornetist King Oliver, who led the band at the Plantation Café. Oliver was a true tragic figure; he gradually lost his teeth and the ability to play to severe gum disease, ended up working as a janitor in a pool hall, and died broke in a rooming house. In the mythology of jazz, his downfall into obscurity and fatal poverty is all the result of his refusal to take a lowball offer for a regular gig at the Cotton Club, which instead catapulted Duke Ellington to stardom. This is the thing to remember: Much of the formative 1930s period of jazz, a music with deep black roots, happened on terms set by white criminals. After the black-and-tan clubs went out of fashion toward the end of the 1930s, the Chicago mob got into coin-operated jukeboxes. Thankfully, they never developed an interest in blues.

Regardless of age or gender, Chicago will turn you into an old man giving directions. Every story reminds of another story, and a story of something that used to be there—because it’s really all one story. After the Outfit took control of policy and bolita, a similar numbers game popular in the city’s Latino neighborhoods, they became absorbed into the gambling and vice empire of the Rush Street crew, whose day-to-day manager went daily to Saul Bellow’s beloved Russian bathhouse on Division Street. The Grand Terrace, having finally gone out of business, became the headquarters of the Democratic congressman William L. Dawson. He was the black sub-boss of Chicago’s political machine, and, in theory, the most powerful black politician of the 1950s. He didn’t redecorate the Grand Terrace. It still had its big neon sign (with a smaller sign with his name added) and its Jazz Age murals and private upstairs clubrooms. The last regular bandleader at the Grand Terrace had been the jazz iconoclast Sun Ra, who was then just developing his sci-fi aesthetic in Chicago.

Dawson’s position within the political machine was a feudal lordship; it was dependent on his ability to bring out black voters en masse. The political machine, in turn, depended on segregation and on interchanges with the underworld. The link between the Outfit’s earlier inroads on The Stroll and the Democratic political machine’s command of the post-war black voting block was made literal and blatant by the continued use of the Grand Terrace. There, Dawson’s landlord was Joe Glaser, the manager of Louis Armstrong and Billie Holiday and a longtime Outfit man. Glaser, who had an early history of walking away from sexual-assault charges, had been a boxing promoter who specialized in fixing fights for the mob and then a manager of black-and-tan clubs. After the repeal of Prohibition destroyed the Outfit’s stranglehold over Chicago liquor, he would rob delivery trucks to stock the bar of the Grand Terrace.

The management company Glaser created—and willed to the Outfit lawyer and power broker Sidney Korshak, unbeknownst to Armstrong—was funded by a loan from Jules Stein, an ophthalmologist, former bar mitzvah musician, and jazz booker for the Chicago mob circuit. Stein’s booking company was MCA, which started with speakeasies and black-and-tan clubs and became the largest talent agency in the world by the end of 1930s, all while being effectively controlled by the Capone organization. It acquired Universal Pictures, and expanded beyond talent management into film, television, music, and publishing. It kept its ties to the Outfit and carried over the city’s culture of patronage to Hollywood, where it encouraged the political ambitions of its client Ronald Reagan. At the start of this century, it merged with Vivendi to create NBCUniversal and Universal Music Group. This is the story of the Outfit controlling who worked in one building in Chicago. It’s a big city. There are many buildings.


If you are ever in Chicago, consider taking a drive through the city at night. Let the car rattle on the badly pockmarked streets. Your eyes will adjust to the amber sear of the General Electric Crimefighters and to that other feature of Chicago nighttimes, the blue flash of a police camera box. There are thousands mounted around the city. Turn down an alley and think of the fact that even in the earliest plat of Chicago, dating to the 1830s, there were plans for alleyways. Park the car, get out, and study how the dimensions and alignment of the streets and sidewalks affect your movements. Don’t think of crime as troglofauna, pale and eyeless, evolving in the dank corners of the city. In Chicago, crime moves, often along currents defined by earlier forms of crime. It’s structural.

Given that they have brought Chicago its most sensationalized coverage since the days of Al Capone, it seems interesting that there have been no real fiction films about the street gangs. Spike Lee’s Chi-Raq doesn’t count. Its portrayal of Chicago’s gangland is pure fantasy, influenced by the mythology of gangsta rap—which is to say, indirectly indebted to Iceberg Slim. Even in fiction, the city can’t escape the myths it inspires. You could say that about drill, our distinctive midtempo flavor of nihilistic trap rap. Drill tends to be oversimplified as the authentic sound of modern Chicago crime, which is how it sells itself, existing as it does in a complicated relationship with the histories and ongoing conflicts of Chicago’s drug gangs, grouped in the increasingly meaningless six-pointed-star Folk and five-pointed-star People alliances.

Really, drill is internet music. It owes its local significance, popularity, and very existence to limitless digital space and social media. Drill is the dizzying, exhaustive braggadocio of Montana Of 300’s “Holy Ghost”; the squishy nausea of Lil Durk’s “Glock Up”; and the hammering of Chief Keef’s “I Don’t Like”; but it is also a thousand guys who can’t rap boasting about the same shit over $50 beats while hustling for Instagram followers and YouTube views. Quality drill albums are nonexistent, and consistent drill mixtapes are rare as hen’s teeth; the ratio of filler to killer is notoriously poor. The mise-en-scène is remarkably consistent from video to video: guns; unimpressive cars; alleys, gangways, and iron gates; ugly weather; those hideous kitchen cabinets that seem to have been installed in every Chicago apartment, regardless of neighborhood. But cheapness and a lack of inspiration are part of the authenticity factor, because drill is immediate. It’s also on the outs, having never crossed over the way that the Savemoney scene made famous by Chance The Rapper and Vic Mensa has.

Nowadays, Chicago crime is defined by the street sets, mostly black or Latino, related by business and varying adherence to the mythology of the gang, prone to violent infighting and splintering. What makes this underworld special is that most of its artistic record is self-produced. These are the patch-sewn cardigans and calling cards of the old-school 1970s street gangs; the outsider literature of the Gangster Disciples’ manuals, more cultish than criminal; the hieroglyphic symbolism of the gang tags that cover Chicago’s alley-facing garage doors; meandering amateur movies in which people pretend to shoot each other with real guns; drill. Despite the early ambitions of the Vice Lords and the Latin Kings organizations, the street gangs have only ever been politically useful as bogeymen. By most estimates, there are around 100,000 street gang members in Chicago, divided into about 60 organizations that are in turn split into about 700 groups. Not every Chicago gang is a violent criminal enterprise, but the majority of murders in Chicago are gang-related, and most of them go unsolved.

There is nothing transgressive about our gangs. Chicago is a place where one can always map the relationship between the criminal and the city. It taught the world that the street criminal could be a charismatic figure and inspired a mythic bestiary of genre archetypes: the terse Mann-ian professional facing obsolescence; the mobster gunning for the throne of the city; the nihilist pimp who knows it’s all part of the game; the folk-hero bank-robber shot by lawmen in the back; the corrupt and colorful wheeler-dealer. But the street gangs can’t be understood on those terms. To an outsider, their public beefs can sound like the sectarian conflicts of a post-apocalyptic religion; witness the bloody feud between the Bang Bang Gang Terror Dome subset of the Black P. Stones and the New Money Killaward subset of the Gangster Disciples, which in 2015 caught the attention of a city otherwise desensitized to the idea of gangland murders.
Screenshot: Candyman

The ongoing social tragedy of murder in Chicago isn’t that there are so many (there are a lot, but it’s never ranked among the top American cities in that respect), but that they are so similar, the same m.o. repeated over and over again. It can reach the point where you almost trick yourself into thinking of the urban gangland as an organism or serial-killer hive mind. But it isn’t. The foibles of the street gangs are very human. And, though we don’t like do admit it, they are relatable.

The French novelist Jean-Patrick Manchette liked to call crime fiction “the great moral literature of our time,” a statement I sometimes find myself agreeing with. There is no more efficient way of putting a character in a moral and existential crisis than a crime, and it is a dark truth of every developed society that, regardless of circumstances, we are all capable of committing a heinous crime. The question of why some do while most don’t directly addresses an important piece of the human puzzle. But in this chapter of the ongoing story of sin in Chicago—the story as told in film, in music, in the media—crime has become a setting, a fact of the neighborhoods, not a question of personalities. No documentary about the day-to-day lives of street gangs (and there are a lot of them, made mostly for TV) has had the wider appeal of Steve James’ Hoop Dreams or The Interrupters—though, of course, none of them are as well made. This is a net positive.But let me posit something that may seem counterintuitive. It isn’t a plea for a return to romanticized crime, though I do think that the forbidden lure of the illegal and immoral can be subverted in powerful ways; it’s something many of the great crime narratives do. But I do think that the art that most cogently addresses crime—whether as a real-world social issue or as an existential state—is art about criminals, because it puts its audience in a compromised spot. There is something of a moral duty to resist the othering of crime. When we begin to think of gangs exclusively as a social phenomenon, instead of as people in groups, we dehumanize not just the gangs, but the people they exploit and victimize, a category that includes the gangs themselves.

One of the more often cited example of this is the 1992 horror film Candyman, which places a supernatural threat within the crime-infested projects. (If you have the time, I recommend watching our short video documentary on the film.) It’s set in Cabrini-Green, which was then the most notorious housing project in Chicago; it was also the home of one of the subjects of Hoop Dreams, the setting of the ’70s sitcom Good Times, and the subject of several documentaries of its own. Candyman is a film that raises some interesting ideas early on, but waffles on them. In the end, it falls back on that all-too-popular image of the urban gangland as a monster, a variant of what one might call the second curse of Chicago—the idea of the city itself as an abstract threat. But it’s always people. Cabrini-Green is gone now, long demolished. In Chicago, it was symbolic of controlled disenfranchisement: a 15,000-person enclave of poverty in an affluent area. The street that ran directly down the middle of the complex—well, you can probably already guess this one. It was Division.

Thanks to Ignatiy Vishnevetsky.

Friday, January 27, 2017

Gangsters & Grifters: Classic Crime Photos from the @ChicagoTribune

Created from the Chicago Tribune's vast archives, Gangsters & Grifters: Classic Crime Photos from the Chicago Tribune, is a collection of photographs featuring infamous criminals, small-time bandits, hoodlums, and more at shocking crime scenes. These vintage glass-plate and acetate negatives were taken from the early 1900s through the 1950s, and they have been largely unseen for generations. That is because most have never been published, only having been witnessed by the photographers and police in the moments after an arrest, crime, or even murder. Included are graphic crime scenes, raw evidence, and depictions of searing emotions, captured on film during a time when photographers were given unprecedented access alongside police. Some photographs resemble film noir movie stills. Some are cartoonish. All feature real people, real drama, and real crimes. Accompanying information about each is included wherever possible, often with archived news stories.

Gangsters & Grifters: Classic Crime Photos from the Chicago Tribune, is a powerful, visually stunning look back into the dark story of Chicago's nefarious crime underworld. These fascinating, surprising, and entrancing photos reveal still-unsolved murder mysteries and portraits of notorious gang overlords like John Dillinger and Al Capone. This is a must-have for photography buffs, history lovers, and anyone curious about the seedy underbelly of early 20th-century Chicago.

Thursday, July 09, 2015

The Fall of John Dillinger and the Rise of the FBI

The movie playing at the Biograph Theater on this hot, muggy summer night was Manhattan Melodrama, starring Clark Gable as the ruthless gangster Blackie Gallagher. But it was the real-life drama starring notorious outlaw John Dillinger that was playing out on the streets of Chicago on this particular Sunday evening that would ultimately captivate the nation and forever transform the FBI.

On July 22, 1934, a nervous Melvin Purvis, Special Agent in Charge of the Bureau's office in Chicago, stood near the Biograph box office. He'd seen Dillinger walk into the crowded theater about two hours earlier with two women, including one in an orange skirt (often called a "red dress") who had tipped off authorities that the wanted criminal would be there. Now, Purvis was waiting for Dillinger to re-emerge.

Suddenly, Purvis saw him. Purvis took out a match and lit his cigar. It was a pre-arranged signal to the Bureau agents and local police officers taking part in the operation, but in the thick crowd less than half a dozen of the men saw it.

In the past year, many such opportunities to catch the wanted outlaw and other gangsters had gone up in smoke. The Bureau had learned many lessons, often the hard way, in the process. Three months earlier, a special agent had been gunned down following a hastily planned raid on a Dillinger gang hideout in Wisconsin. And 13 months earlier, the Bureau had lost an agent and three law enforcement partners at the hands of "Pretty Boy" Floyd and others in the infamous "Kansas City Massacre." But on this night, the Bureau was prepared. The arrangement of agents, the setting of the signal, and the careful preparation were evidence that the Bureau was learning how to catch the most violent criminals. The plan was not perfect, but it was sound, with agents covering all theater exits and directions Dillinger might take.

As Dillinger walked down the street, agents fell in behind him and closed in. Dillinger sensed something was wrong, and as Agent Charles Winstead would later describe, the gangster "whirled around and reached for his right front pocket [where he had a .380 Colt automatic pistol]. He started running sideways toward the alley."

Agents fired. Dillinger fell, mumbled a few words, and died.

The successful conclusion to the Dillinger manhunt was the beginning of the end of the gangster era and a cornerstone in the evolution of the Bureau. With new powers, new skills, and within a year, a new name--the Federal Bureau of Investigation--it was well on its way to becoming a premier law enforcement agency respected around the globe.

Thanks to the FBI

Tuesday, November 15, 2011

J. Edgar Hoover and the FBI's Reputation Soared with High-Profile Arrests of Gangsters

It is fitting to begin in the heart of Washington D.C., where J. Edgar Hoover lies at rest.

He was a local kid who grew up on Capitol Hill, just a few blocks away.

He's buried in his family plot, but Rebecca Roberts, program director at Congressional Cemetery, says former FBI agents built the fence and added a bench - creating a memorial that draws new recruits. "Every now and then some young men in dark suits with little wires coming out of their ears come in the front gate of the cemetery, coming to pay their respects to the director," Roberts said.

The director for an astonishing 48 years, starting in 1924, J. Edgar Hoover became one of the most powerful men in American history - a man who collected secrets and knew how to use them.

He made the FBI a symbol of professional law enforcement and a source of pride for Americans: "The Federal Bureau of Investigation is as close to you as your nearest telephone," Lowell Thomas said in a 1930s newsreel. "It seeks to be your protector in all matters in its jurisdiction. It belongs to you." But Hoover also turned the Bureau into his personal fiefdom: "Presidents were afraid of firing Hoover," said author Ron Kessler. "Congress didn't want to do any oversight. The FBI was a law unto itself."

Kessler has written three books about the FBI. He says that, ironically, in the beginning Hoover, a young Justice Dept. lawyer, was charged with cleaning up a corrupt division. "Hoover emphasized the need for professionalism, not hiring people just because they were friends of someone or family members," Kessler said. "He established the fingerprint operation, he established the indexing system with files."

He also established the FBI Academy, to train agents in crime-busting techniques - making sure he got the credit. In fact, the Bureau's reputation (and Hoover's) soared with high-profile arrests of gangsters like John Dillinger. But out of the spotlight, the director was consolidating his power in another way - collecting dirt. "Hoover, for one thing, would tell for example the head of the Washington field office, 'I want material on Congressmen,' and that would include affairs that they might be having, or they were picked up for seeing a prostitute the night before," said Kessler. "And then he would make sure that they knew that he knew what they had done."

Hoover kept files on celebrities like Marilyn Monroe, John Lennon, Elvis Presley, and even Albert Einstein - "In part because he wanted to have little gossip items to impart to presidents," said Kessler, "or on the other hand, just to maintain his aura as being this powerful person who knew everything."

"That is complete fabrication," said Cartha "Deke" Deloach, now 91, who was one of Hoover's top lieutenants. He insists that if the FBI kept files on public figures, it was for legitimate reasons.

Case in point: The information that President John F. Kennedy was sharing a girlfriend, Judith Campbell Exner, with Chicago mob boss Sam Giancana. "That came to our attention because of a wiretap and microphone that the Attorney General approved, the White House knew about them, that we had on Giancana," said Deloach. "As a result, the White House sometimes would call Exner and it would be overheard by a wiretap."

As for the bugging of Martin Luther King Jr., who feuded with Hoover over the Bureau's enforcement of civil rights, the FBI's alleged justification for tapping King was an investigation into two of his advisers who were said to be Communists. But the taps ended up recording evidence of King's extramarital affairs.

"Hoover was outraged that King was having affairs and projecting himself as a minister, but at the same time Hoover also was jealous of King because he got the Nobel Prize, and that really infuriated Hoover," said Kessler. "Hoover just totally went after him. He would even write letters to people who wanted to give awards to King saying, "You know, we shouldn't do that.'"

Hoover may have amassed information on the sex lives of many prominent figures, but his own personal life has long been the subject of speculation. "There were for years reports and rumors that Hoover used to cross-dress," said Braver.

"Yeah, the rumor that Hoover cross-dressed and wore a red dress to the Plaza was a concoction of someone who actually had been convicted of perjury and was quoted in a book," said Kessler. "It didn't happen."

But how about Hoover's relationship with his top deputy, Clyde Tolson? "Tolson and Hoover would go on vacations together, would take adoring pictures of each other, would have lunch and dinner together almost every single day," said Kessler. "There is no actual evidence of a sexual relationship, but I believe he was homosexual, and that he had a spousal relationship with Tolson."

"Deke" Deloach says he never saw anything other than friendship between the two men, but that Hoover was aware of rumors. "He's actually said to have agents go and visit people and say 'I understand you're talking about the director,'" said Braver.

"I did," Deloach said. "I was told to do it, saying, 'You have made remarks concerning Mr. Hoover being a homosexual. Give me the evidence.' And they'd always back down."

Through the years, under eight presidents, Hoover became so entrenched that he was all but untouchable.

LBJ allowed Hoover to serve beyond the 70-year age limit. He signed an executive order exempting him from compulsory retirement for an indefinite period of time. And Richard Nixon didn't fire him, either. "Nixon was afraid to do it," Deloach said.

"Were people afraid to do it because they were afraid Hoover would go ballistic on them and start leaking out bad stuff about them?" Braver asked. "That was part of it. They were afraid of him."

Hoover died in 1972 at age 77.

His funeral was a state occasion. But shortly after his death, details began leaking of a controversial domestic spying program, known as COINTELPRO, and of Hoover's own personal abuses - for example, using FBI agents to work on his home.

"What do you think happened to Hoover along the way?" asked Braver.

"Hoover, being as powerful as he was and having all this adulation all the time, did think he was God," said Kessler. "Initially he was very far-sighted. He did create this great organization. But as time went on, he became a despot."

Shortly after Hoover's burial, Clyde Tolson, who inherited Hoover's entire estate, bought the closest available plot. And almost 40 years after J. Edgar Hoover's death, we are still wondering about his secrets - Those he used, and those he kept.

Thanks to Rita Braver

Monday, November 14, 2011

Chicago Mob Hangouts in Wisconsin

Members of the U.S. temperance movement believed that eliminating the demon alcohol would cure society of many ills. It would solidify family life, get people back to work, and make society more respectable. Little did they suspect that Prohibition would create effects quite the opposite.

Banning the sale, manufacture and transportation of alcohol from 1920 to 1933 did not cure Americans' thirst for it. In effect, Prohibition forced the supply chain underground. With liquor no longer legally available, gangsters stepped in to fulfill the public's craving.

Chicago was well-known as a gangster city, with mob figures such as Al Capone, Baby Face Nelson, "Polack Joe" Saltis and others. When pressure from the law got hot in Chicago, some gangsters found remote, wooded northern Wisconsin the perfect place to hide out.

Scattered throughout the North Woods are the old haunts of the Capone brothers Al and Ralph, Saltis, Nelson and John Dillinger.

A recent road trip took me back to the remnants of that time when the Roaring '20s, followed by the Great Depression, accentuated the "sin" in Wisconsin. A tour of these historical places is a great way to see the state and learn about an era that affected the development of many small towns of the North Woods.

Among the most well-known stops along the way:

Little Bohemia Lodge in Manitowish Waters: Once a resort where the FBI botched a shootout with John Dillinger's gang and Baby Face Nelson, and recently immortalized by the movie "Public Enemies" with Johnny Depp, it's now a restaurant still called Little Bohemia. The rooms where Dillinger stayed have been turned into a little museum and left mainly as they were, with bullet holes intact.

Dillman's Bay Resort in Lac du Flambeau: Cabin No. 5 is where Baby Face Nelson holed up after the shootout at Little Bohemia, holding an Ojibwe couple hostage for three days.

Minocqua still has several places once allegedly frequented by gangsters, including Norwood Pines Supper Club, which had gambling and a brothel upstairs. BJ's Sportshop on U.S. Highway 51 used to house "Trixies," the most famous whorehouse in the North Woods. The Belle Isle Sports Bar and Grill had a direct line to Arlington Race Track near Chicago. Bosacki's Boat House restaurant also was a popular hangout for the Chicago mob.

Couderay : Al Capone's home on Cranberry Lake was privately operated and open to the public but closed in 2009. Capone used to fly alcohol in from Canada and unload it at his dock. Not far away at Barker's Lake Lodge near Winter, Saltis built a log lodge with cabins for his friends and fellow gangsters. Saltis was a mob boss from Chicago who operated speakeasies. The resort is still open for business and has a nine-hole golf course built by Saltis.

Garmisch USA near Cable: Was built as a lodge by wealthy Chicago businessman Jacob Loeb, who hired the famous attorney Clarence Darrow to represent his teenage nephew after the youth killed another young boy for the thrill. Garmisch still has the beautiful old lodge and now has many cabins as well.

Hurley, Hayward and hell made up what locals called the Devil's Triangle: They were rough logging towns that became notorious for their speakeasies and brothels during Prohibition and were often frequented by the likes of Capone and his cronies. Brothels and bars lined Silver St. in Hurley, where many establishments had tunnels connecting each other, and one allegedly ran under the Montreal River into Michigan. One block of Silver St. still houses strip clubs.

What is now Dawn's Never Inn has the rooms of an old brothel upstairs where Al Capone used to stay.

Mercer : Located on Highway 51 between Hurley and Minocqua, Mercer was the longtime home of Al Capone's older brother Ralph, who ran a couple of taverns. Mitch Babic, now in his 90s, was a fishing and hunting guide for the rich and famous and chronicled Mercer's history over his lifetime with photographs. He knew Ralph well and claims to have been at Little Bohemia on the night of the shootout with Dillinger as a teenager.

Thanks to Gary Porter

Sunday, November 06, 2011

Crime in Chicago Seminar

Join The Chicago History Museum for an exploration of Chicago crime from historical and contemporary perspectives. Programs begin at 7:00 p.m.

Lecture - The Chicago “Outfit:” Traditional Chicago Organized Crime from its Earliest Roots to Operation Family Secrets
Tuesday, November 8, 7:00 p.m.

Arthur Bilek is the Executive Director of the Chicago Crime Commission, a civilian “watchdog” agency that has monitored organized crime activity in Chicago since 1919. Art served under Cook County Sheriff Richard B. Ogilvie in a key investigative role from 1962-1966, and is the author of two books “The First Vice Lord: Big Jim Colosimo and the Ladies of the Levee", and “St. Valentine's Day Massacre: The Untold Story of the Gangland Bloodbath That Brought Down Al Capone.” A recognized authority on the mob and its inner workings, Art will discuss the history of the Outfit from its earliest days through the defining government prosecutions of the 1990s and the recent Operation Family Secrets that has significantly crippled operations locally.
Cost: $10, $8 members


Bus Tour - Murder and Mayhem in Chicago: North by Northwest
Saturday, November 12, 1:00 p.m.-5:00 p.m.

We’ll visit famous North Side and Northwest side crime scene locales and discuss what happened, the aftermath, and their historical implications on life in Chicago and the city’s identity.
Cost: $45, $40 members


History Pub Crawl - Booze, Bars, and Bootlegging! Prohibition Era Chicago
Sunday, November 13, 1:00 p.m.-4p.m.

Find out what makes Chicago untouchable. Get a taste of infamous speakeasies frequented by some of Chicago’s infamous gangsters like Capone, Moran, and Dillinger. On this trolley tour, learn how prohibition came to be, some fascinating facts about the era, and how it ultimately shaped the city and its image.
Cost: $30, $25 members

Film - Madness In The White City
Sunday, November 13, 1:30 p.m.

It’s 1893 and the Columbian Exposition is taking center stage in Chicago. Amidst all the new and wonderful buildings and innovations at the fair, was an evil predator that threatened the lives of many. This film takes a closer looks at the life of H.H. Holmes, one of America's first serial killers. In collaboration with Kurtis Productions. 50 Minutes.
Cost: Free with Museum admission



Lecture - Street Gangs in Chicago
Tuesday, November 15, 7:00 p.m.

John M. Hagedorn is a Professor of Criminal Justice at the University of Illinois and a subject matter expert on contemporary inner-city street gangs. He is the author of “A World of Gangs: Armed Young Men and Gangsta Culture (Globalization and Community),” and a Senior Research Fellow at the University of Illinois Chicago’s Great Cities Institute. Assisted by historian and author Richard Lindberg, Professor Hagedorn’s discussion will be framed around the historical roots of gangs in Gaslight Era Chicago; contemporary gangs and who they are what they represent today.
Cost: $10, $8 members

Bus Tour - Murder and Mayhem in Chicago: South and West
Saturday, November 19, 1:00 p.m.-5:00 p.m.

We’ll visit famous South Side and West side crime scene locales and discuss what happened, the aftermath, and their historical implications on life in Chicago and the city’s identity.
Cost: $45, $40 members

Walking Tour - Crime of the Century: Leopold & Loeb and the Murder of Bobby Franks
Saturday, November 19, 3:00 p.m.-5:00 p.m.

On May 21, 1924, in the city of Chicago, a young boy went missing. The next morning his father, Jacob Franks, received a phone call informing him that his son, Bobby, had been beaten to death. This gruesome and senseless murder has stained Chicago history and still leaves many baffled. Join us as we return to the scene of the crime and tour the Kenwood neighborhood where we will visit sites relevant to Leopold and Loeb’s murder of Bobby Franks.
Cost: $15, $10 members

Friday, July 08, 2011

Chicago & Tourists Embrace Its Mob History and Historic Sites


When Louise Leach planned her vacation, she had three priorities for her visit here: "architecture, pizza and gangsters."

Leach, 63, a retiree from Manchester, England, took an architecture boat tour and by Day Three of her stay had eaten at two pizzerias. She came to the Biograph Theater, where John Dillinger was fatally shot in 1934, for a taste of the gangster life.

"Next we're going to the site of the St. Valentine's Day Massacre, even though I know it's not there anymore," Leach says. "Someone told me the house where Al Capone once lived is still standing, so we'll go there as well. Do you know where I can find some former speakeasies?"

For Leach and her three traveling companions, Chicago's gangster past is part of its allure. "It was quite a dangerous place then, wasn't it?" muses Sally Wetherford, 61. "You see it in the movies all the time, so we simply have to sample it in person."

Las Vegas, St. Paul and Kansas City, Mo., have tours celebrating the often-violent history written by gangsters in the 1920s and '30s. New York has the Museum of the American Gangster. Chicago, though, may relish its links to gangsters more than any other American city.

Bus tours visit the secret bars where they sold alcohol during Prohibition and the places they died. At Holy Name Cathedral, bullet holes from a 1926 gangster shootout are still visible. The Renaissance Blackstone Chicago Hotel, which boasts that Capone patronized its barbershop, offers a "good to be a gangster" package.

"Hollywood got it right. These were exciting, charismatic guys who really captured the imagination of the public," says Jonathan Eig, a Chicago resident and author of the 2010 book Get Capone: The Secret Plot That Captured America's Most Wanted GangsterOrganized Crime Books).

Chicago had a reputation for illicit activity by the 1840s, but the arrival of Capone from New York in 1919 and Prohibition's start in 1920 launched the headline-grabbing reign of criminal groups that ran gambling, alcohol and prostitution rackets. Gangsters here were and are still called the Outfit. The moniker probably originated with Western ranch hands and military buddies, says John Binder, a University of Illinois-Chicago finance professor who wrote the 2003 book The Chicago Outfit (IL) (Images of America).

Binder, who leads tours of gangsters' lavish suburban homes four times a year, says Capone's notoriety during and after his lifetime cemented Chicago's reputation as a rough-and-tumble haven for criminals. "He crossed over from being an historical figure to a legend, like Billy the Kid," he says. "As time goes by, the nasty side of it is forgotten and the fascinating side rises to the forefront. The interest doesn't go away."

One of Binder's favorite spots is the site of the St. Valentine's Day Massacre in a garage where Capone's gang allegedly gunned down seven rivals. At Capone's grave in Mount Carmel Catholic Cemetery in suburban Hillside, he says, admirers often leave whiskey bottles, coins and Valentine cards. Binder doubts Chicago's bloody history taints its current reputation. "It's history," he says. "It's not going to go away, and it's part of what Chicago is."

Jim Peters, president of the preservation group Landmarks Illinois, says the city "has been very hesitant to glorify or recognize" its gangster sites.

Capone's onetime headquarters, the Lexington Hotel, was designated a Chicago landmark by the group for its architecture but was torn down in 1995, he says. An effort to have Capone's home added to the National Register of Historic Places failed.

The Biograph has landmark status "more because of the significance of the building," Peters says.
Craig Alton, owner of the Untouchable Tours, a two-hour bus journey to Chicago gangster locales that's marking its 24th summer, says he had trouble getting city licenses for his business when it began. He believes the city's gangster era is worth commemorating.

"It's history," he says. "We get people who have found this stuff interesting for their whole life. Everybody has a relationship with Al Capone."

Interest in gangsters was one reason Tamotsu Hata and his wife, Yuki, both 29, included Chicago in their first visit to the USA from their home in Tokyo. They took a taxi to the massacre site and planned to stop next at the Biograph.

"We love this part of American history and we have seen many movies about it," says Tamotsu Hata. His wife's favorite was the 2009 movie Public Enemies and the star who portrayed Dillinger. What intrigues Yuki Hata most about Chicago's gangsters? "Johnny Depp."

Thanks to Judy Keen

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