February 14, 2020 — Former Teamsters delegate and Detroit mob associate Chuckie O’Brien died this week at 86 living in retirement in Florida and actively trying to clear his name after decades of most-likely wrongly being implicated in the crime of the century. O’Brien was iconic labor leader Jimmy Hoffa’s surrogate son, for years a top suspect in his famous disappearance and murder and the inspiration for the Tom Hagen character in the book and film, The Godfather. Author and Harvard Law professor Jack Goldsmith, O’Brien’s step son, broke the news of O’Brien’s passing on his blog Thursday, writing that he had died of a heart attack. Last year, Goldsmith penned an excellent book titled In Hoffa’s Shadow, making a very strong and compelling case that his stepdad had nothing to do with Hoffa’s death. O’Brien was booted from the Teamsters in the 1980s due to his connections to a number of high-ranking organized crime figures around the country. Actor Jesse Plemons depicted O’Brien in 2019’s Oscar-nominated movie, The Irishman, with Al Pacino playing Hoffa. The Martin Scorsese-helmed pic was adapted from the book I Heard You Paint Houses, chronicling the relationship shared by Hoffa and Delaware Teamsters boss Frank (The Irishman) Sheeran, who dubiously copped to being the triggerman in the hit in the months before he died of natural causes in 2003 and was portrayed by Robert DeNiro in the film. Hoffa was slain in a dispute with the very same mobsters who put him in power as president of the monolithic Teamsters union years earlier. The film controversially places O’Brien, albeit unknowingly, right in the middle of the conspiracy to murder Hoffa in Southeast Michigan 45 years ago. The fiery 62, year old Hoffa disappeared from a suburban Detroit restaurant parking lot on the afternoon of July 30, 1975. His remains have never been found and nobody has ever faced charges in his mythic kidnapping and murder. O’Brien’s name got dragged into the investigation right away because on the day Hoffa vanished he was in possession of a maroon-colored Mercury Marquis that the FBI believes was used to drive Hoffa to his execution and transport his body to where it was disposed of. The car belonged to Joseph (Joey Jack) Giacalone, the son of Detroit mafia street boss Anthony (Tony Jack) Giacalone, the man Hoffa was on his way to meet at the Machus Red Fox restaurant in Bloomfield Township, Michigan to try and settle a beef between him and New Jersey mob capo Anthony (Tony Pro) Provenzano, also slated to be present. The younger Giacalone’s vehicle was seized by federal authorities on August 9, 1975 and is the only piece of physical evidence ever collected in the case. Hoffa’s DNA was traced to the car’s backseat and trunk. Joey Giacalone and O’Brien was close friends and O’Brien admitted to driving the vehicle the day Hoffa was killed, but always steadfastly denied any involvement in the notorious gangland slaying. While investigators initially considered O’Brien a conspirator in Hoffa’s murder, in recent years, most current and retired FBI agents familiar with the case now dismiss that as a possibility and absolve him of playing a role in the hit. According to Goldsmith’s book, in 2013, the FBI had promised to issue a public statement clearing O’Brien of wrongdoing if he passed a polygraph, however once he did, the statement never came. O’Brien’s biological father was a Kansas City wiseguy. He moved to Michigan in the 1940s with his mom, mob paramour, Sylvia Pagano, who dated Hoffa, Tony Giacalone and other Detroit hoodlums as well as facilitated the business relationship between Hoffa and the mob which went on to fund the 1960s casino construction boom via the plump Teamster pension fund. Hoffa had O’Brien live with him and his family and brought him into the Teamsters to be groomed. In the 1950s and 1960s, it was very rare to see Hoffa without O’Brien by his side acting as his right hand man. By the time Hoffa was on the outs with the mob in the 1970s though — following a prison stint for bribery and fraud —, he and O’Brien were on increasingly bad terms, culminating in a 1974 Thanksgiving meal blowout that resulted in the pair cutting off communication. Hoffa had stepped down from being president of the union when he was behind bars and wanted to reclaim his post. As part of his plan to retake the Teamsters, he distanced himself from the mob and shunned O’Brien, refusing to back him for a administrative position in his old Local 299 located in Southwest Detroit. O’Brien moved to Memphis in the direct aftermath of Hoffa’s murder. Hoffa’s family openly placed blame on O’Brien and told him he was no longer welcome in their home. When author Mario Puzo was researching the mob for what would become his magnum opus, The Godfather, he came across the story of Hoffa essentially adopting O’Brien and used that narrative to craft the relationship between Godfather characters, Don Vito Corleone and his consigliere and surrogate son, Tom Hagen. O’Brien was also very close with Tony Giacalone, referring to him as “Uncle Tony.” Tony Jack died of kidney failure in 2001, awaiting trial for racketeering.
