A Mafia turncoat who ushered in one of the biggest Mob trials in US history is now sharing tales of his former life as a streetwise soldier for the infamous Chicago Outfit, during the fascinating two-hour Family Secrets tour around the Windy City.
‘It’s not just a Mob story, it’s a family story, too,’ says Frank Calabrese Jr., who became so desperate to escape life in organized crime that he ratted out his own father, the Outfit’s Chinatown crew boss, Frank Calabrese Sr., by wearing a wire for the FBI and testifying against him at trial in 2007.
‘Nobody likes to hear their family called dysfunctional and nobody likes to be called a rat, but it is what it is,’ says Frank Jr., 58. ‘I hope that people can get takeaways from it.’
The Family Secrets tour operates several times a week and kicks off from Chicago Chop House in the heart of downtown. Frank Jr., perched at the front of a 37-seat bus, doesn’t hold back on exposing what Mob life is like, warts and all, as he revisits scenes from his family’s crimes and other landmarks.
‘Some things are embarrassing, but in order for people to understand, I have to be straight up with everybody on everything,’ he notes. ‘It does take a lot out of me, because I’m seeing these stories as I’m telling them.
While the bus winds its way throughout the city, including Little Italy, Chinatown and other neighborhoods, Frank Jr. relates his tale of growing up here with a dad who could be kind and loving one minute, then ‘sociopathic’ and ‘explosive’ the next.
He starts the tour with recollections of how Frank Sr., a made man who went by the nickname ‘Frankie Breeze,’ began grooming him at a young age to become proficient in loansharking, gambling and the Chicago way.
One tale he spins is the day Frank Sr. appeared to get into an altercation with a man in the family’s driveway. Upset, Frank Jr., then a teenager, ran and grabbed a baseball bat from the garage and snuck up on the duo.
‘I could see my dad look, and he had this little smirk on his face, like he was all proud of me,’ says Frank, adding there was no fight that day. ‘I didn’t know what my dad was capable of at the time, but years later I was like, “Boy, that guy was lucky.”’
Soon the pair started going on father-son field trips so Frank Jr. could watch and learn. One of his final tests occurred when his dad came home from his ‘so-called work’ and brought him into the bathroom. Frank Sr. turned on the ceiling fan and faucets in case the government was listening.
‘Son, we just killed two guys,’ Frank Jr. recalls his dad telling him as he watched the teen’s face carefully to see what his reaction to the news would be.
All Frank Jr. could think at the time was how his buddies’ fathers probably weren’t having similar conversations in their houses. ‘I’m so excited about it, but I can’t run and tell anybody,’ he says.
Very quickly, recounts Frank Jr. as the bus winds its way through Chicago traffic, he graduated to ‘violence, arson, collections’ and other sketchy gangland behavior. ‘I eventually bought in to all of this, and I was good at it.’
The longer Frank Jr. spent under the tutelage of his ruthless dad, the more Outfit tactics he added to his growing arsenal.
One trick Frank Sr. and other Mob bosses often employed was to tell the aspiring Mafioso they were on their way to kill somebody, even if they had no intention of carrying out a hit.‘They’re just testing you to see if you’re really up to it,’ explains Frank Jr., who today credits his uncle, Nick Calabrese — his dad’s brother and fellow made man — with protecting him from committing the most terrible of crimes: murder.‘I didn’t realize it until years later, but he saved me from my father,’ says Frank Jr. ‘He saved me from crossing a line I couldn’t cross back over.’
That doesn’t mean Frank Jr. didn’t learn how to test his friends’ loyalty by producing a dead body.
On the Family Secrets tour, Frank recounts for his guests the day his dad instructed him to place some sandbags in the trunk of his car and throw a sheet and shovel over them. He then told him to pull up to his pals and tell them he accidentally hit and killed a guy and he needed help burying the body. ‘Let me know how many guys get in the car,’ Frank Sr. told his son.
Hollywood has always played a large role in glorifying Mafia life, and Frank Jr. takes time during the tour to spin some of his favorite related tales, including his memory of seeing Casino, the 1995 film based in part on the Chicago Mob.
“It’s funny, because when I’m watching the movie in the theater I could see that they’re wrong about a lot of stuff, but I had to sit there and shut up because who am I gonna tell?” he laughs.
Talking about the movie, which showcases the Tangiers Casino, the cinematic substitute for the Chicago Outfit’s preferred real-life Vegas hangout, the Stardust, sparks another of Frank Jr.’s recollections.
In 1972, when he was 12, says Frank Jr., he traveled with his dad to Sin City and loved spending his time at the Circus Circus Hotel & Resort’s video arcade. Proving he was developing the chops for manipulation, Frank Jr. says he would wait for his pop to join 20 or 30 of his associates at the dinner table before asking him for money to go play games ‘My dad would give me three or four dollars,’ recalls Frank. ‘Then the guys would say, “Come here kid.” I’d leave there with like $200 or $300 dollars in my pocket!’
On occasion, West Coast royalty would head to Chicago, and Frank Jr. takes his tour bus to Rush Street, once the place to see and be seen for major entertainers, like rumored Mob man Frank Sinatra.
Sinatra, says Frank Jr, had connections to the Mafia, and he claims the Calabreses had ‘direct ties’ to Ol’ Blue Eyes, a Chicago club-scene favorite in the ‘50s and ‘60s, because Frank Sr. was close to the crooner’s longtime comedic opening act, Pat Henry. However, he adds, ‘that doesn’t mean Sinatra was involved in doing illegal activities.’
Despite his family’s familiarity with the glitz and glamour that comes with organized crime, Frank Jr. explains that working in the Mob actually required him to live life under the radar to keep the heat off his family and associates.
‘You learn deception,’ he says. For instance, instead of three-piece suits, fedoras and flashy jewelry, he and his cohorts wore baseball caps, ski jackets and eyeglasses to blend in with their surroundings and not appear too flashy. ‘We didn’t drive Mercedes and BMWs, like you see in the movies. We drove Fords and Chevys.’
And when the older Mob bosses got together to discuss business, it wouldn’t be at a fancy social club.‘They would meet at McDonald’s,’ says Frank Jr. ‘If you walked past them you would think they must be talking about retirement, but they could have been planning a high-profile murder.’
Not that anyone would understand if they happened to overhear. ‘We were so aware of the FBI that everything we did was in code,’ he points out. ‘I could talk to my father in a conversation and he has four names and I have four nicknames. You’d think we were talking about six to eight people and we were really just talking about one another.’
In fact, a discussion about recipes could really be about a hit.
What’s not coded on the tour is Frank Jr.’s refusal to sugarcoat the Mob’s deadlier side, and he goes into detail about the rise and fall of the Outfit’s most infamous upper echelon of villains, including Sam Giancana, who ruled from 1957 through 1966 and was alleged to have played a part in the assassination of John F. Kennedy.
Giancana’s fatal mistake, says Frank Jr., was he became too high profile. In 1975, Giancana was supposedly meeting somebody he trusted in the basement kitchen of his home in Oak Park, Illinois. He wound up dead, shot multiple times in the head and neck. Frank Jr. claims he and the FBI ‘know who did it’ and it was somebody nobody would ever suspect — but he refuses to tell.
Frank Jr. does spill information on his father’s sordid history of hits. He says he found out later in life that Frank Sr. was part of a crew of hit man dispatched to take care of guys ‘causing problems.’ His preferred method of killing, says his son, was ‘to strangle you and cut your throat ear to ear,’ a method Frank Sr. liked to call the Calabrese necktie.
Despite the intense times, life in the Mafia was filled with just as many boring days and nights, especially when it came to casing targets.
According to Frank Jr., surveillance often included getting a windowed van and putting a refrigerator or dishwasher box inside with little holes poked through the cardboard. One of the Outfit’s henchmen would have the unfortunate task of sitting inside the box with two jugs — one for drinking water and another for waste — and staring out at their target to gather information for as long as 24-hour stretches.
Life in the Mob also meant always looking over your shoulder and making sure the FBI wasn’t on your tail. But if they were, Frank Sr. ‘had a sense of humor,’ and he once wrangled the unwitting owner of a Greek diner into helping him throw off the Feds.
Frank Sr. went into the man’s restaurant, sat at the counter and ordered a cup of soup. When he finished, he asked to speak to the owner, who he hugged and shook his hand. When the proprietor asked if they knew each other, the mobster told him no and that he just wanted to compliment him on his fine food. He then darted out the door.
The FBI quickly descended on the diner and its confused owner. Agents demanded to know why he was speaking to Frank Sr., but they refused to buy the man’s pleas of ignorance.
‘Poor guy,’ laughs Frank Jr. ‘My father always used to do that.’
Other times, the mobsters wouldn’t have to worry about police following them because they would head to an auto yard, steal license plates from a car of similar make and model to what they were going to use in a crime and swap them in. ‘If the cops run the number while we’re driving it matches the car and it matches the color so they’re not going to pull us over,’ explains Frank Jr.
One of Frank Jr.’s favorite stories he recounts on the tour is about how his ‘master thief’ father loved to rob weddings. Frank Sr. would take advantage of the fact everyone was drinking and not paying attention to steal the purses filled with cash set aside for the newlyweds. Other times, Frank Sr. would be more brazen and bring a crew to help line up guests against the wall and steal their jewelry.
‘I don’t talk about this like I’m proud of it, but it was what we knew,’ explains Frank Jr.
As time passed, the elder Calabrese became increasingly paranoid and violent, and his son grew desperate to escape the Outfit. ‘I feared my dad more than anything,’ he reveals of the man who once held a loaded gun to his head and threatened to kill him.
Salvation, Frank Jr. says, finally arrived in 1995 when the feds indicted him, his father, and several Outfit crewmembers. He pleaded guilty to charges of racketeering, extortion, mail fraud, perjury and intent to defraud the IRS. The son and dad were eventually incarcerated together in Milan, Michigan, where Frank Jr., sentenced to serve 57 months, hatched a risky plan to free himself from his father’s omnipotence.
He mailed a letter to the FBI on July 27, 1998, and offered to help agents entrap the killer. In what became known as 'Operation Family Secrets', Frank Jr. agreed to wear a wire behind bars and tempt his dad into talking about several gangland murders.
‘I just wanted my father to leave me alone, and the only way I could figure out how to do that was to keep him locked up,’ he says of the life-changing realization.
Frank Jr. was released from prison in February 2000. Seven years later, the 'Family Secrets' trial he was responsible for sparking created a firestorm both in the press and behind the scenes. After testifying on the stand against his dad, Frank Jr. went into a private room, where he had tears rolling down his face because he realized their courtroom confrontation was probably the last time he would see the man alive.
Frank Calabrese Sr., found responsible for 13 murders — likely a fraction of the number he actually committed — died in solitary confinement of heart failure on Christmas Day 2012.
Confirmation he made the right choice by ratting on his dad came when Frank Jr., who wrote the 2011 memoir Operation Family Secrets: How a Mobster's Son and the FBI Brought Down Chicago's Murderous Crime Family, learned Frank Sr. tried to put out a $150,000 contract on his head before he died. He believes one of the big reasons he’s still alive to tell the tale is nobody trusted the cagey Mob boss to actually pay up once the job was completed.
Now ‘every day is like a gift,’ Frank Jr. says. ‘I try to be a good person and I try to surround myself with good people.’
And he gives tours and shares his story as a way to somehow make amends with his dark past.
‘I have to deal every day with what I know,’ Frank Jr. explains. ‘I’m not trying to glorify something. I want people to realize you can change your life around; I want to do something good.’
Thanks to Aaron Rasmussen.
Best of the Month!
- Chicago Mob Infamous Locations Map
- The Chicago Syndicate AKA "The Outfit"
- One Family's Rise, A Century of Power
- Mafia Links of Frankie Valli and the Four Seasons
- THE OUTFIT'S GREATEST HITS
- Top Ten Signs a Mafia Boss is Nuts
- Profile: Harry Aleman
- Firm with reputed mob ties flourishes
- Chicago Alderman Ed Burke Charged with Extortion by Federal Prosecutors #Corruption
- Top Ten Ways The Mafia Can Improve Its Image