Charles O’Brien, James Hoffa Associate, Dead at 86

His mentor's disappearance cast a long shadow over his life

Charles "Chuckie' O'Brien
Charles "Chuckie' O'Brien
Getty Images

Charles O’Brien, a union organizer known best for his close relationship to his mentor Jimmy Hoffa, died last Thursday in Florida at the age of 86.

Besides his own appearances in the news over the years, O’Brien was also known for inspiring a host of high-profile fictional characters, including Tom Hagen in The Godfather. In the recent film The Irishman, O’Brien was portrayed on screen by actor Jesse Plemons.

O’Brien himself became involved in union organizing from a young age, and gradually became close to Hoffa, acting as the labor leader’s assistant for many years.

The aftermath of Hoffa’s disappearance in 1975 would embroil O’Brien for the rest of his life, including allegations that O’Brien had been involved. The book In Hoffa’s Shadow, written by O’Brien’s stepson Jack Goldsmith, explained how his connections to Hoffa shaped O’Brien’s life — and made a convincing case that O’Brien was not involved in Hoffa’s disappearance.

In an editorial for The New York Times published last month, Goldsmith wrote about the government’s surveillance of his stepfather:

When the government leaked some of the transcripts in 1976, in an effort to pressure Chuckie and others, it not only violated his privacy; it also deprived him of the power to define and shape these relationships for himself and the world.

O’Brien’s long life encompassed large swaths of American history, from the labor movement to government surveillance. He leaves behind a complex legacy and a life story that will fascinate students of history for years to come.

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