For both better and worse, Teamster president Jimmy Hoffa was one of the most consequential union leaders of the 20th century. Unlike his very few peers (the Auto Workers’ Walter Reuther and the Mine Workers’ John L. Lewis could both claim comparable historic impact), he also has become the subject of three Hollywood pictures—1978’s F.I.S.T., with Sylvester Stallone ineptly playing a character modeled on Hoffa; 1992’s Hoffa, with Jack Nicholson in the title role; and now Martin Scorsese’s The Irishman, with Al Pacino as the Teamster president.

The source of Hollywood’s recurring fascination isn’t merely Hoffa’s disappearance and apparent execution by the Mafia. It’s also Hoffa himself, whose ego, brilliance, rage, and willingness to employ violent and corrupt means transformed an entire sector of once marginal workers into a blue-collar middle class for several decades, while simultaneously casting unions into a public opprobrium from which it has taken labor decades to recover.

The UAW’s Reuther improved the lives of even more Americans than Hoffa did, but Reuther led a largely puritanical existence that could never provide material for one of Scorsese’s fables of moral descent. Conversely, the mobbed-up thugs who once ran the East Coast longshoremen’s union were so completely indifferent to the lives and fortunes of their members that they’ve made it to the screen only as out-and-out heavies—Lee J. Cobb chewed a lot of scenery playing one in On the Waterfront—but never as protagonists.

With Hoffa, however, you’re plunged into a moral stew where egalitarian initiatives and goonish brutality bubble simultaneously to the surface. What Robert Penn Warren once saw in Huey Long, Scorsese doubtless saw in Jimmy Hoffa.

Sheeran

The Irishman is the tale of a thug who worked on Hoffa’s dark side: Frank Sheeran, a Philadelphia Teamster official who was also a Mafia hit man, and although and because he was close to Hoffa, was presumably the hit man the Mafia chose to end Hoffa’s life. I say “presumably” because Sheeran’s story, which in his old age he related to an attorney who published it after Sheeran’s death, has slim—in some instances, wafer-thin—basis in fact. In his new book In Hoffa’s Shadow, Jack Goldsmith writes that the FBI now believes Hoffa’s killer was a Detroit-based young mobster who died just last year. But whatever Sheeran’s tenuous claims to veracity, his is a tale that Scorsese couldn’t easily resist.

As Scorsese tells it, Sheeran, played by Robert De Niro, navigated by two stars that eventually fell out of alignment—the Teamsters and the mob, personified by his two mentors, Hoffa and Russell Bufalino, the boss of a Pennsylvania Mafia family. Whether working for one or the other or both, Sheeran comes off as a man with catatonic emotions, broken only by outbursts of anger that occasionally peek through his otherwise unruffled acts of violence, decimating his relationship to his family and leaving him alone and unremembered by the film’s denouement.

Sheeran’s delicate balance between unions and the Mafia was shattered when Hoffa was released from prison in 1971 and sought to regain control of the Teamsters, which he’d entrusted when imprisoned four years earlier to a pliable stooge named Frank Fitzsimmons. In Hoffa’s absence, the mob—to whom Hoffa had loaned millions from a Teamster pension fund at usurious interest rates that were lucrative for the union—had taken to looting that fund, to which Fitzsimmons responded with benign neglect and untroubled golf.

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Hoffa’s identification with the Teamsters was so intense he may have determined he’d either retake the union or die trying.

Fitzsimmons’s one initiative had been to transform the Teamsters into a leading political and financial supporter of Richard Nixon. To reward such patriotism, Nixon put one condition on Hoffa’s pardon: He couldn’t have anything to do with the Teamsters until 1980, ensuring Fitzsimmons’s continued control of the union and its obeisance to Nixon for the duration of his presidency and beyond.

Hoffa, who was born in a rage, responded to this new exile with towering fury, hatching all manner of schemes to recapture the Teamsters, even threatening to bring down Fitzsimmons by revealing the union’s subservience to the mob. Bufalino and Sheeran made very clear to Hoffa that the Mafia wouldn’t let him do that, lest this Samson pull down the Temple on them all. On a leisurely car trip to Detroit, Bufalino told Sheeran there’d be a plane waiting to take him on a quick trip to the Motor City, with a gun inside for dispatching his friend. The implication was unstated but clear that Sheeran’s own life depended on this—so Sheeran did the deed.

Were this all that Sheeran confessed to, he might have more credibility. In both the attorney’s book and Scorsese’s film, however, he pads his résumé by recounting how he also transported guns for the Bay of Pigs invasion and the weapon used for the JFK assassination, not to mention how he whacked mob renegade Joey Gallo in a Greenwich Village clam house.

To the suitably skeptical, Sheeran comes off less as a one-man death squad and more like Zelig with a gun. To believe he participated in all these epochal ventures, you’d have to believe the Mafia had a very small talent pool.

Chuckie

A minor character in Scorsese’s film is Chuckie O’Brien, whom it depicts as a sometime Hoffa gofer. Following what has been one of the few aspects of the Hoffa murder mystery that is common to most narratives, Chuckie is shown picking up Hoffa in a restaurant parking lot and unknowingly transporting him to the house where Sheeran sends Hoffa to his end.

Anticipating that Scorsese would film this scene as Sheeran recounted it, Harvard law professor Jack Goldsmith has risen to Chuckie’s defense with In Hoffa’s Shadow, timed as a counternarrative to Scorsese’s picture. No mystery attends Goldsmith’s choice of topics: He is Chuckie’s stepson. And in penning his stepdad’s apologia, he has added considerably to our knowledge of the byzantine interactions between Hoffa and the Mafia.

Goldsmith chronicles a life at once more tragic and comic than Sheeran’s—more tragic because Chuckie’s ties to both Hoffa and the Cosa Nostra were deeper and more emotionally overwhelming than Sheeran’s; more comic because as an “associate” of the mob rather than a member (he wasn’t Sicilian on his father’s side), and an inveterate screw-up, his tasks were entirely nonviolent. And three times out of four, he botched those, too.

On January 3, The New York Times ran an op-ed by Goldsmith pointing out two features of the Scorsese film he deemed flat-out wrong. First, he wrote, Chuckie did not drive Hoffa to his murderers, nor did he have any awareness that day that Hoffa—the closest thing Chuckie ever had to a father—was about to be killed. Second, the film showed Sheeran playing the role in Hoffa’s life that Chuckie had actually played. As Goldsmith wrote, “It was Chuckie, not Mr. Sheeran, who for decades served as Mr. Hoffa’s ‘intimate companion, driver, bodyguard and special troubleshooter’” (that characterization is from New York Times labor reporter A.H. Raskin).

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Many Teamsters not only forgave Hoffa for his excesses; they positively reveled in his transgressions.

Chuckie’s actual father ran out on his family in the 1930s, when he was a small child. His mother, Sylvia, soon moved the family to Detroit and went to work for Hoffa’s Teamster local, and later as a bookkeeper for the Detroit mob’s numbers racket. If ever a boy’s worst friend was his mother, it was Sylvia.

When Chuckie was nine, she introduced him to Hoffa. Jimmy took a shine to the boy, had him summer with his family at a lakeside cabin, taught him to drive, called him his stepson, and treated him as he would his own child. A year or two later, Sylvia also introduced Chuckie to Anthony Giacalone (Uncle Tony), her numbers racket boss, who became Chuckie’s other, sterner mentor. By age 12, Chuckie was collecting numbers picks from autoworkers at the gates to Ford’s River Rouge factory. At age 19, he took a job at Hoffa’s Detroit local and became his body man; in the same year, at Uncle Tony’s prompting, he also took an oath to the Detroit mob: “On my honor, I will never betray any relationship I have with any of you.”

Did I mention that Sylvia became the primary liaison between Hoffa and the Mafia, and Chuckie the courier between the two? In the early 1940s, Uncle Tony was providing muscle for a lumberyard that was resisting Hoffa’s efforts to unionize it. After Sylvia introduced them, Hoffa cut a deal with Tony to give his boys stolen lumber trucks if he’d switch sides, which Tony did—the first such deal between Hoffa and the mob. FBI phone taps decades later revealed mafiosi crediting Sylvia with persuading Hoffa to make the loans that enabled the mob to build more than half the hotels on the old Vegas Strip.

After years of service to the Teamsters and the Mafia, the two halves of Chuckie’s world came into violent collision on a hot July afternoon in 1975. Chuckie spent the final day of Jimmy Hoffa’s traceable life bumming rides and driving around Detroit in borrowed cars (including one from Giacalone’s son) on a host of errands. Goldsmith argues persuasively that the fact that Chuckie was carless that day makes it highly improbable that he served as Hoffa’s final chauffeur. You don’t assign the role of get-there (as opposed to get-away) driver to a guy without a car, using a vehicle registered to the son of the city’s ranking mafioso.

In classic hapless Chuckie manner, he’d had a falling out with Hoffa some months before and actually spent part of the day of Hoffa’s abduction waiting for a ride in the very parking lot from which Hoffa was taken. He was a logical suspect for something, and retained that ambiguous status for decades. However, the fact that he voluntarily met with the FBI within days of the abduction, and that the mob didn’t thereupon whack him because they knew he knew nothing specific about the killing, suggests his innocence, in which Goldsmith notes that FBI agents on the case eventually came to believe.

When Chuckie discovered that Hoffa had been abducted, he paid an immediate call to his Uncle Tony, who had been meeting for months with Hoffa to tell him, in effect, what Joe Pesci’s Russell Bufalino character tells Hoffa in The Irishman: that if Hoffa didn’t shut up about Mafia corruption of the Teamsters, the mob would dispose of him. With Chuckie terribly upset and with Hoffa missing, Good Uncle Tony told him, “Life is very funny, Chuck. Things happen, and you don’t have control over it.”

That was Tony-speak for the Bufalino line to Sheeran in The Irishman: “It is what it is.”

× Expand Charles Kelly/AP Images Jimmy Hoffa leaves the Federal Building in Nashville following his arraignment on one of the multiple charges the feds would bring against him (June 7, 1962).

Hoffa

Both The Irishman and In Hoffa’s Shadow show a desperate Jimmy Hoffa engaging in inexplicable behavior. In the face of the government’s prohibition of his return to Teamsters leadership, and intensifying threats—actually, guarantees—that if he continued in his quest the Mafia would have him killed, Hoffa persisted. Goldsmith speculates that by the end of his life, Hoffa may have become suicidal—that he’d determined he would either retake the Teamsters or die trying.

That Hoffa’s identity was so wrapped up in leading the Teamsters requires us to understand the nature of both his leadership and his union. The key, I think, is that the Teamsters were peculiarly Hoffa’s—more than the Mine Workers were Lewis’s or the UAW Reuther’s. Unlike other unions, the Teamsters grew as, and partly because, Hoffa—a rare charismatic leader with a clear strategic vision—centralized power: first to the city body, then the regional, then the national, which is to say, Hoffa.

In the early years of the 20th century, the Teamsters were a collection of small, autonomous locals, grappling with an industry composed of small, autonomous employers. The need for a powerful national organization wasn’t apparent to local leaders, who had no desire to surrender their clout to some higher-up performing no discernible task. Dan Tobin, who headed the union from 1907 until 1947, never even persuaded convention delegates to establish a nationwide death benefit for members.

During the upheavals of the early 1930s, however, Teamster locals in Minneapolis, under the leadership of Farrell Dobbs, started to work together to refuse to unload goods shipped across jurisdictions and across town unless the trucking company agreed to unionize. Their actions culminated in a general strike that won them a citywide contract with a multiplicity of employers, and Dobbs schooled the young Hoffa in how to organize by using the Teamsters’ regional power to bring employers to heel.

What had worked in Minneapolis, Hoffa reasoned, could work in Detroit. And throughout the ’40s and early ’50s, as trucking slowly began to eclipse rail, Hoffa intervened to interdict shipments to grow his union across broader and broader terrains, crafting contracts that covered all of Michigan, and then all the Midwest. Local leaders sometimes resented the loss of autonomy that accompanied such regionalization, but Hoffa had developed into a dynamic speaker who convinced rank-and-file members that he was their champion, and produced the contracts that backed that up—salving local leaders’ egos and pocketbooks with financial rewards.

Labor academics like Harvard’s John Dunlop viewed Hoffa’s “area contracts” as an innovation in labor relations. They bore some resemblance to Germany’s regionwide contracts in a number of industries, which in recent decades have provided many German workers with higher pay and benefits than their American counterparts. They also heralded the sectorwide bargaining that other European nations have embraced.

In 1957, Hoffa was elected Teamster president, and began campaigning for a single nationwide truckers’ contract. Over the next seven years, constantly traversing the country, he schooled his members in the logic of sweeping, multi-employer contracts: telling Los Angeles workers in 1961 how he’d won higher wages all across Arkansas, telling New York workers in 1962 how he’d won higher wages across Los Angeles, telling Philadelphia workers in 1963 how he’d won higher wages across New York. In late 1963, seeing the handwriting on the wall, more than 800 trucking companies agreed to sit down with Hoffa to bargain a single nationwide contract.

In January 1964, the two sides came to terms—Hoffa’s terms. The National Master Freight Agreement set wage, pension, and health insurance standards which every employer was required to meet. Every one of the approximately 450,000 Teamster truckers (close to half of all truckers in America) was covered by the contract. The New York Times termed the agreement “one of the most significant developments of the postwar period.”

The deal led to an immediate jump in incomes in parts of the country where pay standards were low, particularly the South. To get that deal, Hoffa had had to win support from locals in parts of the country where work paid more handsomely than the standard. He included riders to the contract that allowed locals to bargain for pay and benefits above, but never below, the national floor. Goldsmith writes that the mob-controlled unions in places like New York also helped by squelching any dissent.

In building support among members for the contract, Hoffa established a rapport with the rank and file that no other union leader appeared to possess. His appeal wasn’t just in the merits of his arguments, but in his manner of speaking—abusive to critics, the establishment, the federal officials trying to put him in jail for jury tampering. Hoffa was the drivers’ guy, spewing bile at authority. Think Donald Trump, if Trump directed his attacks solely at wealthy elites, not minorities or immigrants, and solely for the benefit of workers. Like Trump’s legions, Hoffa’s not merely forgave him his excesses; they reveled in his transgressions.

The same posture, however, took its toll in public opinion. In early 1957, during his campaign for the Teamster presidency, Hoffa was made to testify before a senatorial committee probing corruption in the labor movement. Headed by longtime Southern reactionaries, the committee was determined to use the hearings as a basis for new, anti-union legislation. They were abetted by their young general counsel, Robert Kennedy, who took every opportunity to demean and ridicule the witnesses in general and Hoffa in particular. Throughout the nationally televised hearings, Hoffa responded with belligerent indifference to the charges of violence and corruption, displaying a hatred of government duplicity and bourgeois morality that his members relished but that the television audience found appalling.

In January, before the hearings began, Gallup found unions’ approval rating was at an all-time high of 75 percent. By the time the hearings had concluded in September, that rating had fallen to 65 percent, beginning a decades-long slide. The hearings, labor historian Nelson Lichtenstein has written, “had a devastating impact on the moral standing of the entire trade-union world.” For decades thereafter, companies would invoke the Teamsters’ reputation for violence and corruption in their campaigns to dissuade their workers from unionizing.

Hoffa went to prison for jury tampering in 1967, effectively ending his very personal reign over what then was the nation’s largest union. His North Star, wrote two academics who’d followed his campaign for the National Master Freight Agreement, had always been “power aggrandizement for himself and the union, the building of an industry-wide contractual structure under a single unified command—his own.”

No wonder he raged at his inability to take it back.

After the Fall

Thirteen years after Hoffa disappeared, the great edifice of economic advancement he’d constructed began to crumble. In 1980, in a bipartisan act of Congress demanded by President Carter, the trucking industry was deregulated. In short order, new entrants not bound by the National Master Freight Agreement flooded the industry, while established employers refused to renew its terms. Where once more than a thousand trucking companies adhered to its provisions, by 2008, only five companies remained in the national employers’ organization Hoffa had compelled the industry to assemble. Today’s truckers still drive the roads, but the middle-class wages and benefits their forebears once received have been largely relegated to the history books.

Throughout the 1970s and ’80s, the Teamsters grew steadily more mobbed up, until 1990, when the government finally ousted its leaders and began monitoring and restructuring the union. In 2015—with the union cleaned up and the mob decimated—the government lifted its oversight. Today, like its peers, the Teamsters are a union embattled by corporate and Republican existential hostility to labor, but at the same time are engaged in numerous organizing campaigns and generally progressive political initiatives.

In 1980, as deregulation was about to descend on American truckers’ livelihoods, the Teamster old guard tried one more old-school tactic. Teamster President Roy Williams sought to persuade Senator Howard Cannon, Democrat of Nevada, to kill the bill in committee. His method of persuasion, which Cannon rejected and for which Williams subsequently did time, was an attempted bribe.

Those of us who mourn the disappearance of a large and thriving middle class might wish that for one last time, this Hoffa-esque ploy had succeeded.