How The Feds Finally Toppled Detroit Mafia Czar Tony Giacalone

In the months and years after the disappearance of Teamsters union power Jimmy Hoffa, which famously took place in Metro Detroit exactly 40 years ago this summer on July 30, 1975, Motor City mob chieftain Anthony (Tony Jack) Giacalone, the prime suspect in the notorious gangland slaying, became Public Enemy No. 1 for the federal government.

Giacalone, the Detroit mafia’s street boss and day-to-day overseer, has been dead since 2001 (kidney failure), but back on the afternoon Hoffa vanished in 1975, he was scheduled to meet the fiery labor leader for lunch at the Machus Red Fox Restaurant – a lunch date Tony Jack didn’t keep, instead spending the afternoon at his Southfield Athletic Club headquarters five miles down the road. The FBI believes that Giacalone sent a crew of assassins to scoop him up and deliver him to his slaughter. Nonetheless, Tony Jack, nor anybody else was ever charged in the Hoffa hit, reportedly carried out for Hoffa’s refusal to retire from union politics at the mob’s request and discontinue his bid to get re-elected International President of the Teamsters after a five-year prison sentence for fraud, bribery and jury-tampering.

Having avoided arrest for his well-known role in Hoffa’s murder, Giacalone had a major target on his back – the feds put him in their crosshairs and went after him full-tilt, intent on bringing him down by any means necessary. They achieved their goal. Twofold.

Before the end of the decade, the steely-eyed and deadly-as-cancer Giacalone (a suspect in over two dozen gangland killings) would be convicted in two separate cases and serve seven years behind bars as a guest of the United States government in an Atlanta federal penitentiary. First, he was found guilty of federal tax evasion charges at a jury trial in 1976. Then two years later, he pled guilty to extortion charges following being the lead suspect in a racketeering case out of Saginaw, Michigan, a working-class community roughly 100 miles north of Detroit. He served his pair of prison sentences concurrently.

The tax case was Al Capone-style, who’s bloody Prohibition Era-reign in Chicago as the country’s first true gangster celebrity came crashing down in the wake of his ordering the iconic St. Valentines Massacre (the killing of seven Irish mob rivals), for not paying enough income taxes, not murder.The feds in Detroit took the same approach in their campaign to incarcerate Tony Jack in the aftermath of the Hoffa ordeal.

Giacalone was convicted for not paying proper taxes in the calendar years of 1968, 1969 and 1970. While the government calculated Giacalone’s net-worth at well over a million dollars, he was only reporting less than $75,000 annually.

“We’re talking about a man who enjoyed the finer things in life and that just didn’t match up with what he was claiming to the government every year on his tax return,” former U.S. Prosecutor Richard Zuckerman recalled. “We went into his home and we found a closet filled with very expensive, Italian-made, custom-designed suits and shoes. He was eating at the best restaurants in town every night and traveling all over the place. He liked the job he had, he liked and reveled in being a mob boss. He liked scaring people. But got he got sloppy with his finances or at least accounting for them. And that gave us an angle to go after him on the tax indictment. Everyone knew he was responsible for probably countless murders, put the whole Hoffa execution together, however, he was always able to cover his tracks. In this particular case, he didn’t and we nailed him.”

Shortly after Giacalone’s conviction, his son, Anthony (Fat Tony) Giacalone, Jr, at that time an aspiring mob thug who often acted as his dad’s driver, was indicted and eventually jailed for perjury – he testified untruthfully at his father’s trial that the $25,000 the FBI found in Tony Jack’s bedroom upon his arrest was cash that belonged to him and was money he received as part of the more than $125,000 he got as presents at his wedding years earlier.

His brother’s car, Tony Jack’s youngest boy, Joseph (Joey Jack) Giacalone’s maroon, four-door mercury marquis sedan is believed to be the lone piece of physical evidence recovered in the Hoffa case – it resides in the basement of FBI headquarters in downtown Detroit. Joey Jack’s Mercury is suspected to have been used by the killer’s in Hoffa’s kidnapping and possibly for the transportation and disposal of his dead body (traces of his DNA were discovered in the vehicle’s backseat and his scent detected in the trunk by police dogs).

Tony Giacalone boasted a lengthy arrest record (a rap sheet with a litany of offenses dating back decades), however up until his pair of convictions in the late 1970s, he hadn’t done much prison time. Plucked off the streets of Eastern Market (the epicenter of Detroit’s one-time Little Italy) by longtime Michigan Godfather Joseph (Joe Uno) Zerilli in the early 1940s, Giacalone came up in the Motor City rackets as Zerilli’s bodyguard and go-to enforcer.

Tony Jack’s troubles in Saginaw resulted from a satellite crew the Detroit mob had operating in the area since the Prohibition years. The Giacalones had family ties in Saginaw, located in the heart of the Tri-City area, between Flint and Bay City, like the so-called “Sagnasty,” hardscrabble regions with lunch-pail mentalities and high crime rates.

Giacalone’s father-in-law was Giacomo (Big Jack) Provenzano, the Saginaw crew’s leader from Prohibition until his death of natural causes in 1970. Provenzano, a produce-business owner, was first cousins with New Jersey-based Genovese crime family captain Anthony (Tony Pro) Provenzano, the other top suspect in organizing the Jimmy Hoffa assassination beside Giacalone and his baby brother and fellow capo Vito (Billy Jack) Giacalone.

Tony Pro, a close friend-turned-bitter-enemy of Hoffa’s, as well as a powerful Teamsters union boss on the east coast, was supposed to be at the lunch meeting at the Red Fox that never happened alongside Hoffa and Tony Jack, but rather was playing cards at his union hall in New Jersey. He’s thought to have sent members of his crew to Michigan to help clip Hoffa instead.

After Big Jack Provenzano passed away, the Detroit mafia’s Saginaw crew was inherited by Big Jack’s grandson and the Giacalone brothers’ nephew, a brash, polished, thirstysomething mobster named William (Billy Lee) Loiacano. Stationing his affairs at the Pasta House restaurant in Saginaw, Billy Lee and his ragtag inner-circle made up of a rogue’s galley of goons, thieves, scam-artists, bookies, shylocks and drug dealers, known on the streets as “The Pasta House crew,” ran roughshod over the Tri-City underworld, invoking fear in the community not felt since Big Jack’s early days and enforcing a street tax on narcotics transactions and black numbers houses, a pair of businesses Big Jack had stayed away from in the past.

Billy Lee and his boys began to get the reputation as cowboys, the exact opposite of the traditional Detroit mob mold, a picture of stability and relatively low-key behavior, which always came in vast contrast to the other La Cosa Nostra franchises across the country.

“That Tri-City up there was pretty rough for a period in the 70s, we’d send word all the time to the Giacalones’ nephew, Loiacano, to quiet down and stop making so many waves,” said one former Giacalone crew member. “I actually think Tony and Billy Jack liked it, they certainly weren’t discouraging it as much as they could. They wanted to empower the kid up there, make him a big shot. He started to act like his uncles and in those towns he was operating up there, it sticks out more, attracts more attention. It didn’t do any of those guys any favors, they all got pinched and Tony was right there with them.”

In addition to his own rackets, Loiacano was also in charge of watching over the Tri-City interests of his uncles, Billy and Tony and other Detroit Mafiosi like Giacomo (Black Jack) Tocco and Anthony (Tony the Bull) Corrado. Tocco was the acting boss of the syndicate in the 1970s. Tony the Bull was his cousin and a capo in the regime. They co-owned Robertson Linen Service, a prominent business brand in the Tri-City area back then. The Giacalone brothers staked Loiacano’s gambling and loansharking operations.

When people in the region got out of line, they got dealt with swiftly and forcefully. Numbers runner and drug pusher David De La Rosa wouldn’t pay tribute and owed money to the mob for his gambling debts, so he got whacked out by Loiacano’s top muscle, Norman (Pete the Arm) Crawford at Crawford’s after-hours club. Local car dealer owner Robert Dean testified in front of a grand jury investigating the crew and Loiacano dispatched two of his soldiers, the LeBreche brothers (Bruce and Brent), to deliver a vicious beating. Contractor Gerald Yeager wouldn’t cough up a street tax for construction jobs he was working and the LeBreche brothers paid him a visit for a pummeling, too.

Sometimes Loiacano would reach out to his uncle Tony for help in collecting. The incident that led to Giacalone’s ensnarement in the Saginaw crew’s racketeering case stemmed from a business relationship-gone-sour and law suit involving Loiacano and Tony Dambro, a local builder. Dambro sold Loiacano the liquor license for the Pasta House and agreed to construct the restaurant for him. The problem was once Billy Lee assumed ownership of Dambro’s liquor license and the eatery opened for business, he decided against forking over all the money. In the end, Dambro was paid less than the agreed upon amount for the liquor license fee and flatout stiffed him in the construction job, Loiacano deeming the craftsmanship insufficient. Feeling he had no other options, Dambro sued Billy Lee and his wife and Pasta House co-owner, Tony Jack’s niece, for payment of the outstanding debt.

Bumping into each other at a restaurant in the weeks after the lawsuit was filed in early 1978, Loiacano threatened Dambro.

“This time you went too far, we chop motherfuckers like you up, put you in a box and dump you in the river,” Billy Lee said to Dambro.

A phone call a few days later, heard Loiacano tell Dambro, “We’re waiting outside your house ready to blow your fucking head off.”

A run-in at a mutual friend’s office saw Billy Lee scream at Dambro, “Don’t you know who I am and what I can do to you, cocksucker?”

It only got worse. To Dambro’s surprise and great discontent, Tony Jack himself showed up at his apartment and in Sicilian demanded $100,000 to lift the multiple murder contracts that were on his head. That was all he could take. Terrified for his life, Dambro dropped the lawsuit and paid the Giacalones and Loiacano the 100k. Then he called the FBI.

Arrested in the fall of 1978, Billy Loiacano’s Pasta House crew were all tried in 1980 and convicted on racketeering charges. Today, the 75-yeart old Loiacano is retired from the mob and living in Tampa, Florida, having hung up his gangster spurs a long time ago in exchange for work as owner of a chain of fruit markets.

Released from prison in 1986, Tony Giacalone continued his rein atop the Detroit mafia until the day he died in 2001, not shockingly, under indictment and awaiting trial on another racketeering case. Billy Giacalone, suspected by the FBI of being his older brother’s “rep” on the Hoffa hit, pled guilty in that case, admitting his membership in the mafia as part of a plea deal, and died of natural causes in 2012.

According to FBI records and informant logs, in the weeks after Tony Jack was sprung from the clink in January ’86, he and Jack Tocco (by then the Family’s official don) led an induction ceremony, “making” his two sons, Fat Tony and Joey Jack Giacalone. Alleged to be included in the Detroit mob’s “Class of ’86” was Billy Giacalone’s son, Jack (Jackie the Kid) Giacalone.

Fat Tony Giacalone died in 2013 of cancer. Per several sources, Jackie Giacalone, 65, assumed the Family’s boss’ chair from a dying Jack Tocco last year and Joey Giacalone is one of his most-trusted capos.

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3 comments

  1. Sean

    Does anyone here have an opinion on Frank Sheeran’s story/confession on the Hoffa disappearance, expressed in the book’I heard you paint houses’?

    • Yes, we talk about it in our new documentary “Killing Jimmy Hoffa”. Sheeran was sometimes hitman for the Mafia, but he also tried to sell his story for years…he eventually realized that saying HE was the triggerman would get him a book deal, so that’s what he did. His story is not credible for a slew of reasons we go into in the film.

  2. MightyDR

    Much thanks, good article. Seems a bit weird that Tony Jack would show up at this Dambro’s house himself and demand money. Was that the only way the FBI tied him into the racketeering case?