The book was shut on the federal government’s last full-scale assault against the Detroit mafia ten years ago this spring, resulting in prison time for two reputed high-ranking members of the organization and the acquittal at trial of the case’s lead defendant, alleged Motown mob don Jack (Jackie the Kid) Giacalone. The feds indicted Giacalone and 14 co-defendants in March 2006 on racketeering, sports gambling and money laundering charges. Most of those named in the case pled guilty in March 2007, however, the 66-year old Giacalone, the Tocco-Zerilli crime family’s then-street boss, decided to fight the charges in court and was found not guilty at a jury trial the following month.

Also indicted in the case was Giacalone’s current reputed street boss Peter (Petey Specs) Tocco and Giacalone’s protégé and former driver David (Davey the Donut) Aceto, an alleged capo these days. Pete Tocco, 70, and Davey Aceto, 59, both pled out and did two years apiece behind bars. Tocco is the nephew of deceased Detroit mob boss Giacomo (Black Jack) Tocco, who passed away peacefully of heart failure in the summer of 2014 after over three decades on the throne.

While Tocco was released from the clink on Christmas Eve 2009, Aceto got sprung in April of 2010. In the years since they got out, Tocco became Giacalone’s street boss and Aceto received a bump up to a capo spot on the city’s eastside, per sources on both sides of the law.

Jackie Giacalone has been convicted of federal gambling and racketeering charges twice, once in the mid-1980s and again in the early 1990s. His father was legendary Motor City mafia luminary Vito (Billy Jack) Giacalone. The elder Giacalone died of natural causes in 2012. He was a daily attendee at his son’s April 2007 trial. At the time, authorities pegged Billy Giacalone as Jack Tocco’s underboss.

The trial itself didn’t go well for the government, as the prosecutor’s main witness against Jackie the Kid failed to hold up on the stand. Giacalone was charged with trying to extort local high-rolling Detroit gambler and renowned playboy Don DeSerrano out of $350,000. DeSerrano allegedly owed the Detroit mafia for unpaid gambling debt and reportedly was levied a “tax” for operating rigged card games.

In the early 2000s, the handsome and always well-dressed DeSerrano, known on the streets as “Dee Dee” or “Debonair Don,” was the biggest gambler in Southeast Michigan, according to court records. When he was informed of his debt, per the court filings related to the indictment, DeSerrano sought aid in dealing with Giacalone from an old school area bookie named Vince Fiorlini, a reputed associate of Billy Giacalone’s and a handicapper and card-game expert who worked for Giacalone crew gambling bosses Allen (The General) Hilf and Freddy (The Saint) Salem.

DeSerrano had a meeting with Jackie Giacalone, Hilf and Fiorlini in 2004 to discuss his debt, per court records. When called to testify at Giacalone’s trial, DeSerrano said he never felt threatened by Giacalone. The jury concurred and came back with a not guilty verdict on April 28, 2007.

“Jackie took the dice in his hand and threw some good combinations at the proverbial craps table,” joked retired U.S. prosecutor Keith Corbett of Giacalone’s gamble going to trial.

Hilf, one of the largest bookmakers in America for decades, was the younger Giacalone’s best friend until he died suddenly of kidney failure three years ago. He was an unindicted co-conspirator in the 2006 case. Salem died of natural causes in 2009. Hilf and Salem ran the primarily non-Italian Capital Social Club crew in tandem.

Corbett, the main mob buster in Michigan at the U.S. Attorneys Office for close to four decades, recalled a run-in with Billy Giacalone in an elevator during Jackie Giacalone’s trial – Giacalone was prosecuted by Corbett in the landmark Operation GameTax case of the late 1990s and did six years in prison.

“I got into an elevator after one of the court proceedings concluded for the day and Billy Jack was there with a big smile on his face,” Corbett recollected. “I said ‘what’s so funny, Billy?’ and he goes, ‘Mr. Corbett, I want to thank you for sending me to prison, it was the best thing I could have done for my health, I’ve lost almost 50 pounds’ or something like that. I turned to him and said ‘Bill, you know that’s great, it was my pleasure and if you give me the chance I’d be more than happy to do it again.”

Jackie Giacalone


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