Longtime Detroit mafia street boss Anthony (Tony Jack) Giacalone always publically denied any connection to or knowledge of the disappearance and gangland murder of spirited labor union leader Jimmy Hoffa, without question America’s most notorious unsolved crime which is marking its 40th anniversary this month. In private, it was a completely different story. Tony Jack enjoyed using his reputation as the villainous mastermind of the infamous kidnapping and assassination as currency in the underworld, per a number of reported incidents and first-hand accounts, most gallingly in his attempt to extort Hoffa’s protégé-turned-rival and successor as Teamsters president Frank Fitzsimmons in the years after Hoffa vanished in the summer of 1975. According to FBI documents, Giacalone (pictured as a young goodfella in the feature photo & dead since 2001), tried shaking down Fitzsimmons for $250,000 dollars in the winter of 1978 in relation to Hoffa’s execution and was partially successful. Tony Jack bluntly informed Fitzsimmons at a meeting in Florida that he did him a favor by getting rid of Hoffa, in essence paving the way for his reelection to office in 1976, and if he didn’t deliver a lump sum pavement of 250 large in return for an effort that brought Giacalone even more squarely into the federal government’s crosshairs than he already was, he’d kill him. Fitzsimmons paid Giacalone a portion of the extortion money however was able to buy time and stave off further attempts to collect the cash until Tony Jack was shipped away for a seven-year stint in the can months later. During the days that they were allies, the diminutive, broad-shouldered and high-energy Hoffa and the tall, chubby and more low-key Fitzsimmons made an odd, yet incredibly prolific pair. With “Big Fitzy” by his side watching his back, Hoffa climbed the ranks of the Teamsters, first locally in Detroit in the 1930s and 40s and then nationally and worldwide in the 1950s and 60s, as the fiery labor leader built the trucker and cartage workers union into a massive political power. Fitzsimmons was Hoffa’s vice president at his Michigan Local (Southwest Detroit’s Local 299) and eventually his international VP following his ascent to the Teamsters Presidency. At least a share of Hoffa’s rise in the organized labor movement, if not more, is directly attributed to his mob ties, specifically his deep links with Italian mafia factions in Detroit, Ohio, Chicago, New York, Pennsylvania, Florida and New Orleans. One of the key entry points into his mutually-beneficial arrangement with the mob from early on in his career was his relationship to Tony Giacalone and Giacalone’s mentor, legendary Motor City Godfather Joseph (Joe Uno) Zerilli. Giacalone, Zerilli and their associates (men like underboss Angelo Meli and capos Pete Licavoli and Santo Perrone) provided Hoffa muscle and an introduction to other mafia luminaries across the country for him to build inroads with and grow his powerbase.The mob in return got free run of the union itself, jobs, contracts and access to the Teamsters overall coffers and pension funds to loot. Zerilli, widely beloved, respected and revered in underworld circles on multiple continents, sat on the American mafia’s National Commission until he died of natural causes in 1977. Giacalone, a suspect in literally dozens of gangland slayings and a man that reveled in his role as a terrifying hoodlum, was the face of the Detroit mob in the last half of the 20th Century. Upon Hoffa’s imprisonment in 1967 (convicted for bribery, fraud and jury tampering), he named Fitzsimmons his temporary replacement, maintaining the official title even though he was behind bars. As Fitzsimmons negotiated a Presidential pardon with Richard Nixon in the early 1970s, Hoffa was convinced to officially resign his post as boss of the Teamsters as a gesture of good will, presumably under the promise that he would be allowed to get his job back once free. Big Fitzy either didn’t get the memo or got too comfortable in the boss’ chair to care. The Teamsters’ backers in the mob had a different idea as well. The consensus in the mafia was it wanted Fitzsimmons to remain in the president’s seat – being he was much easier to control – and Hoffa to voluntarily retire. Hoffa and Big Fitz circa 1966 Realizing that was probably wishful thinking, they sought insurance. In the proverbial 11th hour of talks, Fitzsimmons quietly got Nixon to add a clause in the pardon barring Hoffa for running for re-election for 10 years. Unaware of the last-minute added language, Hoffa agreed to accept Nixon’s pardon and walked out of his Pennsylvania federal prison cell in December 1971. Learning of his restrictions in reclaiming the union in the days after his release, he was livid and vowed to fight it and the mob for that matter if he had to in order to take back the Teamsters presidency he lusted for badly. He blamed Big Fitzy, who he viewed as a traitor, for the pardon double-cross and openly cursed him. Per several FBI informant logs, Hoffa sought on more than once occasion to place a murder contract on Fitzsimmons’ life for his betrayal. Once his parole was lifted in early 1974, Hoffa embarked on a media tour denouncing his former friends in the mafia and telling anyone who would listen that if he was allowed to return to power he intended of ridding the Teamsters of any and all organized crime influence. Word began spreading that Hoffa had a good chance of getting the pardon clause ruled unconstitutional by the courts and the pulse of the union rank-and-file showed he’d easily unseat Fitzsimmons in the 1976 election if cleared to throw his hat into the ring. The mafia eliminated the problem by eliminating Hoffa. Most experts concur, Tony Giacalone, Hoffa’s contact in the Detroit mob dating back as early as the 1940s, was tasked with coordinating his murder. Hoffa disappeared on the afternoon of July 30, 1975 en route to a sit down at a Bloomfield (Tony Jack’s cousin via marriage). Neither Tony Pro nor Tony Jack showed up for the sit-down and Hoffa got into a car believed to have belonged to Giacalone’s son in the restaurant’s parking lot and drove away with three unidentified men never to be seen or heard from again. Hoffa was desperate to quell tensions with Provenzano, needing Tony Pro’s east coast mob-puppeted Teamsters voting block to win a potential election. Tony Jack’s younger brother and fellow feared Michigan mafia capo Vito (Billy Jack) Giacalone is believed to have been Tony Jack’s representative on the Hoffa hit. A number of lieutenants working under both Tony Giacalone and Tony Provenzano are suspected of carrying out the slaying and the disposal of the body on their behalf. The “Two Tonys” themselves were at their respective headquarters – Tony Jack at the nearby Southfield Athletic Club and Tony Pro at his union hall in Jersey – at the exact time Hoffa was done away with. No arrests were ever made and charges have never been filed in the case. Detroit mob chieftain Anthony “Tony Jack” Giacalone circa 1975 In the weeks leading up to Hoffa’s kidnapping and homicide, Fitzsimmons’ son, Richard (Little Fitz) Fitzsimmons, had his car blown to pieces while it was parked outside a popular Local 299 hangout, Nemo’s Bar & Grille, and he and his dad dined inside. Nemo’s is located in between Local 299 and the now torn-down Tigers Stadium. Little Fitz was opposing Hoffa loyalist Dave Johnson in the race for the presidency of 299 at the time of the car bombing, an incident investigators peg as the exact point when Hoffa’s death warrant was signed. The FBI theorizes Hoffa either ordered the bombing himself as an intimidation tactic and possible attempt on the lives of both Big and Little Fitz as retribution for their disloyalty or rival forces in the Teamsters perpetrated it trying to make it appear that Hoffa had gone too far. Big Fitzy coasted to victory in the ’76 Teamsters presidential election with Hoffa out of the way. Tony Giacalone felt that he was responsible for laying the necessary groundwork that allowed Fitzsimmons to waltz back into office and wanted financial compensation, according to FBI records regarding labor-union corruption. Summoning Fitzsimmons to a dinner at Miami’s Joe Sonken’s Gold Coast Restaurant & Lounge in January 1978, Giacalone demanded $250,000 for rubbing out Hoffa two and a half years prior and in turn getting him elected. He threatened to kill Big Fitzy if he didn’t cough up the cash immediately. Sonken’s restaurant was a well-known mob hangout in South Florida, a congregating spot for gangsters spawning from a variety of mafia crime families around the U.S for almost 50 years. It closed its’ doors in 1994. A Jewish Chicago Outfit associate, Sonken opened his Gold Coast haunt in 1948. Sonken was alleged to have been a pimp and bookie back in the Windy City before migrating south after WWII. The summer after Fitzsimmons met Giacalone at the Gold Coast Restaurant, Big Fitzy got a visit at his palatial Washington D.C. office from one of Tony Jack’s labor-union lackeys, Chuckie O’Brien, a Detroit mob associate and Jimmy Hoffa’s surrogate son. Per court motions filed years later, O’Brien wanted to know why Fitzsimmons hadn’t paid Giacalone the 250K Giacalone had “requested.” O’Brien’s visit worked and elicited a payment. Shortly thereafter, Fitzsimmons’ son, Little Fitz, shuttled a $25,000 installment to Tony Jack in Michigan. Chuckie O’Brien circa 1975 Big Fitzy didn’t pony up any more money though. Probably because Giacalone went to prison – on January 2, 1979, Tony Jack reported to a federal correctional facility in Atlanta to serve a 10-year sentence for tax evasion and extortion related to a Detroit mafia satellite crew in Saginaw, Michigan ran by his nephew. Giacalone was paroled after seven years and returned to his gangland throne in early 1986. He died 15 years later of kidney failure under another federal racketeering indictment. Fitzsimmons died of cancer in 1981. Little Fitz would go on to be jailed for taking kickbacks. O’Brien, someone investigators think may have lured Hoffa into Giacalone’s son’s car that fateful July day 40 years ago, was booted out of the Teamsters union in 1988 due to his mob ties. He admits to having possession of the vehicle in the hours leading up to Hoffa going missing. Currently 80, O’Brien resides in Florida.