June 11, 2021 — Reputed Detroit mob boss Jack (Jackie the Kid) Giacalone dodged the penitentiary by paying $12,000 to Uncle Sam last week related to a civil back-taxes case he’s been dealing with for the past four years.
U.S. District Court Judge George Steeh held Giacalone in contempt several weeks ago for failing to make payments on his more than $500,000 tax debt. Steeh gave Jackie the Kid until last Thursday to begin to settle up or risk going to prison. He finally wrote a check. He’ll be writing $2,000-to-$4,000 checks on a monthly basis going forward if he wants to avoid being back in the same predicament.
According to federal records, the 71-year old Giacalone has not paid any income taxes since 2004. He refers to himself simply as a “gambler.” Uncle Sam thinks it’s a little more complicated than that and has hounded Jackie the Kid and his family for the better half of the last century.
The feds have believed for quite some time now, that Giacalone controls all illegal gambling in the Metro Detroit area. Per sources, Giacalone was voted in as don of the Detroit mob in 2014, but had been serving as street boss for the outfit for over a decade.
Giacalone hails from distinguished mafia stock. Longtime Detroit mob street boss Anthony (Tony Jack) Giacalone was Jackie the Kid’s uncle and capo and underboss Vito (Billy Jack) Giacalone was his father. The infamous Giacalone brothers were the faces of the Tocco-Zerilli crime family from the 1960s until their deaths in the New Millennium and their passing of the torch to Jackie the Kid, who had been being groomed for the job since he was in his 30s.
Back in 2007, Giacalone beat a racketeering and extortion case in federal court, found not guilty at a jury trial. Despite his legal victory in the case, he still has a pair of federal bookmaking and conspiracy convictions on his record and did a combined five years behind bars as punishment in the 1980s and 1990s, respectively.