A son probes his stepfather’s ties to Jimmy Hoffa

Jack Goldsmith untangles a family relationship that involved links to the mob and the 1975 disappearance of Teamsters Union president Jimmy Hoffa.

Jack Goldsmith, who is the Henry L. Shattuck Professor of Law at Harvard University, couldn’t have chosen a more different career path than that of his stepfather, Charles “Chuckie” O’Brien.

O’Brien was Teamsters Union President Jimmy Hoffa’s confidante and he also had close ties to the organized crime figures suspected in Hoffa's still unsolved 1975 disappearance. O’Brien could never shake suspicions that he drove Hoffa to his abduction.

It’s not surprising that Goldsmith distanced himself from his stepfather as he moved toward adulthood and aspired to an elite legal career. He changed his name and ultimately cut O’Brien out of his life altogether.

They would reconcile decades later after Goldsmith’s experiences in the post-9/11 Justice Department made him rethink his views about government overreach. Having his own kids made Goldsmith question his decision to cut off the only father figure he’d ever known.

With “In Hoffa’s Shadow: A Stepfather, a Disappearance in Detroit, and My Search for the Truth,” Goldsmith set out to understand exactly what, if any, role O’Brien played in Hoffa’s disappearance and perhaps cast his stepfather in a better light.

I’m not spoiling anything by saying he doesn’t solve one of the greatest mysteries in American history, a puzzle that’s eluded two generations of FBI agents and countless amateur sleuths. Others can decide whether Goldsmith has unearthed anything new about Hoffa’s disappearance.

Regardless, Goldsmith has produced a wonderful book about the complicated relationship between a deeply flawed stepfather and the adopted son he loved deeply and forgave unconditionally for casting him aside.

O’Brien’s trajectory is largely fixed by two father figures he met as a child after his own dad abandoned him: Hoffa and Detroit mobster Anthony Giacalone, whom Hoffa was supposed to meet on the day he vanished.  

O’Brien, much to his detriment, remained equally loyal to Hoffa and the Teamsters and to Giacalone and the Cosa Nostra, though his mixed Italian-Irish heritage meant he couldn’t become a made-man himself.

Goldsmith pulls no punches, portraying O’Brien as a tragic although not entirely sympathetic figure.

O'Brien is not the savvy consigliere Tom Hagen of “The Godfather,” whom author Mario Puzo modeled on O’Brien and Robert Duvall later played in the movies. Rather, O’Brien comes off as a loyal but often hapless sidekick who dutifully carried out Hoffa’s directives, whether they involved attempted jury tampering or still more cringeworthy tasks.

He and a Teamsters colleague once paid a friend at the Wayne County Morgue $1,000 for a cadaver’s head that they boxed, wrapped, and delivered to the editor-in-chief of The Detroit News. The newspaper had angered Hoffa with its critical coverage of the Teamsters.

Still, Hoffa thought O’Brien was too unreliable to run a union local.

Goldsmith doesn’t excuse O’Brien’s misdeeds. But he comes to view his stepfather’s experience as a target of then-Attorney General Robert F. Kennedy through the prism of his own experiences reviewing the legality of new surveillance powers granted after the 9/11 attacks.

“It turned out that the Justice Department, as Chuckie had always said, was a dangerously powerful institution with surveillance and prosecution powers that, in pursuit of a righteous cause, were easy to abuse,” Goldsmith writes.

Goldsmith argues that the zealous Teamster prosecutions permanently damaged organized labor’s public image and opened the door for far worse mob infiltration after Hoffa went to prison in 1967.

Goldsmith also makes the case that O’Brien wasn’t involved in Hoffa’s later abduction, a view shared by many FBI agents involved in the investigation. More likely, O’Brien was simply in the wrong place at the wrong time as the mob sought to silence Hoffa before he exposed the cushy relationship between the Teamsters and organized crime.

O’Brien’s “eccentric integrity” as Goldsmith calls it and fealty to omertà, the mob’s code of silence, would never allow him to be completely honest about what he knew, even with his own son.

He and Goldsmith had only one entirely unguarded conversation during which O’Brien dished a bit about what role some organized crime figures might have played in Hoffa’s murder. He quickly came to regret his candor but never insisted on keeping it out of Goldsmith’s book – or even reading the manuscript when given a chance.

“Maybe he wanted the secrets out, but didn’t want the knowledge of, and thus the responsibility for, their publication,” Goldsmith writes. “Maybe he wanted to clear his name at any cost. Or maybe he knew how long and hard I had worked on the book, and he decided to sacrifice his honor and pride out of love for me.”

“I never asked,” Goldsmith adds.

Seth Stern is a Bloomberg Law editor and co-author of “Justice Brennan: Liberal Champion.”