June 4, 2021 – Reputed Detroit mob boss Jack (Jackie the Kid) Giacalone turns 71 this week. Next week, he might have to turn himself into jail.

Last month, Giacalone was held in contempt in his civil tax case in U.S. District Court in Detroit for failing to make payments on his over a half-million dollar debt to the IRS. U.S. District Court Judge George Steeh gave Jackie the Kid until June 3 to pay $14,500 for a first installment of his debt and produce the names of the people sending him money orders over the past year or go to prison.

Giacalone has fought disclosing the names for fear they will be harassed by the FBI. It is unclear at this time what option Giacalone chose Thursday. He claims financial hardship as the reason he has failed to pay back any of the monies owed to Uncle Sam. According to federal records, Giacalone has not paid any income taxes since the early 2000s

In April, Giacalone and his wife were awarded a $29,500,000 jury verdict against an ambulance company in Las Vegas for negligence in their daughter’s emergency medical care spawning from an incident in March 2013. Chantel Giacalone, 35, had an adverse reaction to a peanut allergy while modeling at a trade show hosted at the Mandalay Bay hotel and casino and is currently in a vegetative state being cared for at the Giacalone residence in West Bloomfield, Michigan. The gigantic jury award received wide-spanning media attention across the United States. The Giacalones did an interview with People Magazine.

Jackie Giacalone, a self-proclaimed “gambler,” comes from a vaunted mob dynasty in Detroit: his dad, Vito (Billy Jack) Giacalone and his uncle, Anthony (Tony Jack) Giacalone were the Tocco-Zerilli crime family street bosses from the 1950s until their deaths in 2012 and 2001, respectively. The Giacalone brothers are the top suspects in the disappearance and murder of Teamsters boss Jimmy Hoffa, who famously vanished from a Bloomfield Township, Michigan restaurant parking lot on July 30, 1975 en route to a lunch meeting with Tony Giacalone.

Hoffa’s remains have never been found and nobody has ever been arrested in the case, which remains an open investigation today. Hoffa and the mob were butting heads over leadership in the mammoth truckers labor union. The Giacalone brothers were responsible for “operating” Hoffa as an asset of organized crime, according to FBI intelligence reports. Jackie the Kid was just 25 years old the summer Hoffa went missing and a eager up-and-comer in his father’s crew headquartered in Detroit’s historic Eastern Market district.

Back in 2007, Jackie Giacalone beat a racketeering and extortion case in federal court, found not guilty at a jury trial. Despite his legal victory 14 years ago, he still has a pair of federal bookmaking and conspiracy convictions on his record. Per sources, Giacalone was “made” at a 1986 ceremony, promoted to a capo post in the 1990s and replaced his uncle Tony Jack as street boss in 2000. Multiple sources claim Giacalone became the Godfather of the Detroit mob in early 2014, taking the reins from an ailing Giacomo (Black Jack) Tocco, who led the crime family bearing his name for nearly four decades and passed away from heart disease just a few months later.