Chuckie O'Brien, Jimmy Hoffa’s Confidante and Surrogate Son, Dies at 86

February 14, 2020, 12:57 AM by  Allan Lengel

Chuckie O'Brien (Family photo)

Chuckie O'Brien, Jimmy Hoffa’s confidante, “surrogate son," driver, gofer and conduit to the mob, died Thursday in Boca Raton, Fla., at 86. The cause of death appeared to be a heart attack, his stepson said.

O'Brien became somewhat of a household name after the disappearance of Hoffa in July 1975, and the FBI quickly named him as a suspect. The feds theorized that he drove the car to Hoffa's death at the behest of the mob that wanted to keep the ex-Teamster boss from regaining power in the union. Hoffa experts, including journalists Dan Moldea and Scott Burnstein,  subsequently theorized that the driver was more likely Detroit mobster Vito Giacalone.

No one has ever been charged.

Just recently, O'Brien's stepson, Jack Goldsmith, a former Justice Department official who now teaches at Harvard Law School, wrote a book, "In Hoffa's Shadow," which laid out convincing evidence that O'Brien couldn't have driven the car that day.

Goldsmith tried to get the feds to write an official letter clearing O'Brien in the Hoffa caper, and the FBI and U.S. Attorney's Office seriously considered it. But in 2014, then-U.S. Attorney Barbara McQuade decided against it. Goldsmith hoped the feds might change their mind after his book was published.

I wrote a column here Dec. 4 headlined "Time For Feds To Clear Chuckie O'Brien In Hoffa Murder," based on information in the book and my interviews, which included a former FBI agent who worked on the case.

I wrote:

FBI agent Andrew Sluss, now retired, picked up the case in 2003.

He entered the investigation with the institutional belief that O’Brien was the likely wheelman for Hoffa’s last ride. But “within a year,” Goldsmith writes, “Sluss had concluded that this belief was erroneous and that Chuckie was not at the Machus Red Fox parking lot that afternoon. …Sluss also apparently studied the timeline of Chuckie’s activities during the afternoon of July 30 more carefully than the original investigators, and concluded that it was practically impossible for Chuckie to have picked up Hoffa...based on his known whereabouts that afternoon.”

As for Goldsmith’s account of the Hoffa investigation, Sluss tells Deadline Detroit: “I think it’s 100 percent accurate.” And he says with “no hesitation” that O’Brien is entitled to be formally exonerated with a letter.

Jack Goldsmith: "Chuckie lived ... under that shadow." (Photo: Harvard Law School)

There had been rumors of late that the U.S. Attorney's Office was considered re-examining O'Brien's role, but on multiple occasions when I inquired, the official word was there would be no comment.  

In a column Thursday in an oline publication, Lawfare, Goldsmith writes about his stepdad's death:

Chuckie was most famous for two things. In the 1950s, 1960s and early 1970s, he was the closest aide and near-constant companion of Jimmy Hoffa, the infamous and influential leader of the Teamsters Union. And following Hoffa’s disappearance on July 30, 1975, Chuckie became a leading suspect when the government publicly accused him of picking up Hoffa and driving him to his death. The latter charge is, I believe, untrue. But practically everyone believed it. This accusation was repeated in story after story and book after book and, most recently, in the movie “The Irishman.” Chuckie lived the last 44 years of his life under that shadow.

I explain in my recent book, “In Hoffa’s Shadow,” why I do not think Chuckie was involved in Hoffa’s murder. But, as I also explain, Chuckie knew many of the other leading suspects well— and after Hoffa disappeared, he became tragically ensnared between the government’s public accusations and pressure and the mob’s very different types of private pressure. As one FBI agent on the Hoffa case in the 1970s told me, “For some reason the gods just decided to position [Chuckie] where so much of his life would be chewed up in the clash between an implacable government and an implacable Mafia.” The clash of implacables ruined Chuckie’s life—it cost him his job, his reputation, many of his friends, and his honor.

To me, Chuckie was, most of all, a great father. He became my father when I was at a vulnerable point in my life at age 12. Despite the unbearable pressures of the Hoffa investigation, Chuckie was a constant source of love, stability, encouragement and even inspiration. I broke with him in my 20s for reasons I came to regret deeply. But in 2004 I sought his forgiveness and he gave it without question. One of the great joys of my life was our time together during the last 16 years, when we learned a great deal about one another and grew very close.

While writing my column in December, Goldsmith told me that O'Brien was still mentally sharp, but was declining in health.

"I very much hope that the government will do the right thing and give Chuckie the letter it promised him,” he said. 

“It would mean a ton to Chuckie, who for 44 years has proclaimed his innocence. Imagine if you were publicly, but falsely, accused by the government of picking up your father figure and driving him to his death; imagine if you would want exoneration.”

O'Brien is survived by his wife Brenda; his daughter Josephine and his son Chuckie; three stepsons, including Jack Goldsmith and his brothers Brett and Steven and by numerous grandchildren.

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