As an 19-year-old hustling odd jobs around Boston, I happened to be behind the wheel on the set of the ’93 thriller Malice, starring Alec Baldwin and Nicole Kidman. With roots in trucking that run four generations deep in Medford, I wasn’t much for savoring white wine and hors d’oeuvres with Hollywood’s elite. Yet, I formed a bond with Tom Cruise, who was then married to Kidman, often hanging out on the set during filming days.
On the set,” O’Brien reminisces, “I was the youngest person there, and he frequently approached me for conversation.” Over time, they developed such a strong bond that they organized a touch football game involving Baldwin and a band of Teamsters during their free days.
The scene reveals more than just Tom Cruise’s friendly demeanor as a worker. It provides a glimpse into the fascination of International Brotherhood of Teamsters general president O’Brien with the entertainment industry and its connections, a desire to be associated with Hollywood and promote his agenda in ways that extend beyond casual social gatherings. Lately, after his contentious speech at the Republican National Convention last summer, the union boss, now in his 50s, has become one of the rare figures in the industry who wields influence in the Trump administration, an uneasy alliance that has caused concern among Hollywood’s liberal community.
Even though some may link the Teamsters primarily with big rigs, as a fan, I can attest that they’re an indispensable part of the film and TV industry scene. With roots in Hollywood dating back to the Great Depression, their 15,000 members play a pivotal role behind the scenes. They not only drive equipment ranging from set decorations to transporting talent, but also cast some of the stars themselves (approximately 700 casting directors within the industry are Teamsters). They also scout locations for production, train set animals, and ensure that both cast and crew are well-fed.
A bold, working-class figure with a knack for challenging highbrow Hollywood personalities, O’Brien often showcases his tattoos on his black veterans’ group T-shirt during podcast appearances, regaling listeners with anecdotes from his Boston union days. He aspires to transform the influence of the entertainment industry in Washington and safeguard its future. Currently, he is vigorously advocating for a federal tax credit, backing Trump’s 100% tariff on foreign productions, and urging Apple and Amazon to be reined in due to perceived negative impacts on the industry. However, it remains uncertain whether his efforts will make him the bridge to Washington that the industry has been yearning for or simply a publicity seeker more focused on gaining viral video fame than promoting a healthier Hollywood.
O’Brien’s narrative isn’t merely about the rise of a blue-collar influencer in showbiz politics – it delves into the intricate bond between the raw environment of Boston’s white working class and an entertainment industry, located 3,000 miles away, that keeps depicting this setting. At times, O’Brien appears more like a character from the latest Ben Affleck or Mark Wahlberg film than a shrewd political figure who is friends with both of them.
Sean O’Brien combines traditional hardness with modern media skills seamlessly at times, as demonstrated when Oklahoma Republican Sen. Markwayne Mullin proposed a fistfight during a hearing about unions affecting working families. This unusual scene in Congress had Sean O’Brien as its focal point, and he appeared ready to accept the challenge until Sen. Bernie Sanders intervened to cool down the situation. The incident gained wide popularity online, making Sean O’Brien a familiar name to millions who previously didn’t know him.
In a groundbreaking move for contemporary Republican and especially Trump-era politics, O’Brien has established an unprecedented position – a figure who can represent the interests of Hollywood directly from within the White House. However, an essential query lingers: Is it Hollywood that truly desires his presence?
At the Republican National Convention, there was an unusual buzz in the air. Sean O’Brien, a prominent figure known for leading one of the country’s biggest and most influential labor unions, had made an unprecedented move by addressing the GOP gathering. Typically, labor leaders would appear at the Democratic National Convention, but this unexpected speech might have been the reason why O’Brien wasn’t extended an invitation afterwards.
During his speech, O’Brien advocated for a significant shift in favor of the union. Interestingly, during his campaign to lead the union, he had criticized Trump and instead praised then-President Joe Biden and a Democratic-controlled Congress in 2021 for passing the COVID stimulus bill. This bill was crucial for the financial stability of a pension fund serving approximately 400,000 Teamsters, as it faced significant opposition on Capitol Hill. Vice President Kamala Harris played a pivotal role by casting the deciding vote in the Senate to advance this legislation.
At a recent debate with my opponent, Steve Vairma, I expressed my heartfelt appreciation to everyone who put in the effort on that project. It’s regrettable that many of our members supported Donald Trump during his presidency, a term which I previously referred to as a ‘four-year reign of terror’ due to the actions of the National Labor Relations Board under his leadership.
The shift in stance by O’Brien in Milwaukee, where he praised Trump as “one tough SOB” (a strong compliment from a Teamster), made this change all the more noteworthy.
The fact that O’Brien, in Milwaukee, called Trump a “one tough SOB” (a significant praise from a Teamster) added weight to his unexpected transformation.
Or:
The Teamster compliment O’Brien gave Trump in Milwaukee, calling him “one tough SOB”, made the sudden change in his stance even more surprising.
Experts struggled to decipher O’Brien’s strategy. Jonathan Weisman from The New York Times Politics wondered if he was secretly sabotaging the Big Business party. However, a simpler interpretation could have been valid as well: O’Brien might have been expressing a shift towards working-class populism that was becoming evident in certain Republican circles (a point that O’Brien would later validate by aligning with Missouri Republican Senator Josh Hawley, who has taken a similar stance). According to a pre-2024 election poll conducted by the Teamsters, around 60% of members expressed support for Trump, as per O’Brien.
One reason suggested for leaning towards Trump is straightforward political pragmatism, according to the leader. “We’ve never had this level of access before,” states O’Brien, who identifies as a Democrat but admits he still holds that label. He claims to engage in regular discussions with the president – at least twice or thrice monthly – which is significantly more frequent than his interactions with Biden. According to O’Brien, these conversations primarily revolve around current events and Trump shows great empathy towards our relationship and working people.
Despite O’Brien’s ambiguity about the specific outcomes of their phone conversations, he does point to a notable development: Lori Chavez-DeRemer being appointed as Labor Secretary. This choice, seen in Washington as a form of reciprocity for O’Brien’s decision not to endorse Harris among his 1.3 million members, is significant given the numerous departments under Trump that seem to be working against their intended goals. However, some progressive groups like The Nation have criticized Chavez-DeRemer as being anti-union. O’Brien remains vague about other accomplishments, mentioning only that they have been consulted on various issues by the administration and have access and credibility.
The approval for this matter hasn’t gone down smoothly among certain parts of the Teamsters’ management. Richard Hooker Jr., the secretary-treasurer of Local 623 in Philadelphia, opines that the close relationship with the White House has severely undermined both the Teamsters’ reputation and their objectives.
Hooker expresses his disapproval to THR, stating, ‘We’re being ridiculed within the labor community due to the general president’s affinity for Trump.’ He continues, ‘In essence, when you’re a labor leader, it means standing up for all workers. So when approximately 50,000 TSA employees lose their right to unionize, and the most powerful voice in the labor movement remains silent, that speaks volumes to employers about their freedom to act as they wish.’ This silence, he implies, refers to O’Brien’s lack of response to the government’s decision in March to weaken workers’ rights at the Homeland Security department.
Instead of keeping the White House as a frequent contact, according to Hooker, Teamsters should roll up their sleeves and join the fray alongside everyone else, aggressively resisting Trump and his administration. This Philadelphian is vying for the union leadership position against O’Brien in next year’s elections.
From my perspective as a gamer, I’d say it’s been pointed out that O’Brien seems to side with Trump beyond just practical gain, leaning towards the politics of tough-guy white males. Much like the president, O’Brien sees himself as a shrewd negotiator and unfortunately, he’s also shared anti-immigrant views. He stated, “I think the biggest issue is people are trying to protect illegal aliens who come here and commit crimes, and that’s unacceptable,” during his conversation with Hawley on his podcast.
Sean O’Brien, as Joe Allen, a left-wing author and former Teamster who often critiques O’Brien on Counterpunch, points out, has disguised his actions under the guise of bipartisanship. However, in reality, he seems to be currying favor with the far right by exploiting the weaknesses of the Democrats. Regardless of one’s political stance, it’s hard to deny that this isn’t beneficial for labor unions. Allen also highlights that under Trump, organizations like the NLRB and OSHA are essentially dysfunctional, while ICE is targeting working-class families instead of protecting them.
It’s possible that critics could become a source of annoyance for O’Brien, but even those who are not fond of him acknowledge his skill as a political tactician. Despite having no formal education in politics and leaving the University of Massachusetts at Boston after just one term to work as a heavy-equipment driver for his father’s union, O’Brien has demonstrated an uncanny ability to manipulate those who initially disliked him. An example of this is his successful takeover of the left-leaning faction Teamsters for a Democratic Union before his 2021 election. Although his opponent was chosen by the incumbent, James P. Hoffa, O’Brien still managed to win the race, running on a reform platform that promised tougher negotiations with UPS. This victory came as a shock to some members and observers, but since then, Teamsters for a Democratic Union has largely followed O’Brien’s lead.
It’s quite noticeable that O’Brien, even casual social media users might remark upon this, has been frequently engaging with Republican leaders on entertainment industry matters recently. He’s been snapped in photos during these encounters, such as when he discussed film tax credits with Texas Governor Greg Abbott in the Lone Star State, or chatted about the Paramount-Skydance merger with FCC chair Brendan Carr.
O’Brien mentions that he and Trump often discuss entertainment-related matters. Lately, this union leader has been discussing with the President topics such as federal tax credits and tariffs for overseas production. The Teamsters were ardent supporters of Trump’s plan regarding tariffs, but since the President announced it in May, it appears this initiative has not moved forward.
O’Brien and Lindsay Dougherty, leader of the Teamsters’ film division, expressed gratitude towards President Trump for courageously advocating for decent union jobs at a time when others have looked away. This action is a significant stride in addressing the long-standing issue of Hollywood studios over-relying on outsourcing work that should be done locally,” they stated following Trump’s controversial post on Truth Social. Other labor unions in Hollywood were more reserved in their response.
O’Brien appeared on Fox News to support the proposal, winning over numerous supporters of former President Trump. He gave the plan an aura of endorsement from the American film industry by stating, “Impose tariffs, make them manufacture in the U.S., and accept slightly lower profits.
Growing up, O’Brien developed a strong connection with Hollywood. His father, Billy O’Brien, who served as a transportation coordinator for over five decades with Boston’s Local 25, frequently scanned through trade publications to find his next job opportunity. Notably, he secured significant roles in productions like Clint Eastwood’s 2003 film “Mystic River” and the classic Boston movie “Good Will Hunting.” O’Brien’s appreciation for gritty cinema was ingrained at an early age as well. He admired the gangster movies “Goodfellas” (which he claims to have watched thousands of times) and “State of Grace” (having seen it a hundred times), both released in 1990, and continues to revisit these films even now.
The concerns expressed by the labor leader regarding Hollywood echo sentiments that many townsfolk subtly voice: a shift toward tech domination. While studio executives have long been seen as adversaries by organized labor, O’Brien expresses a melancholic tone when discussing their management of a tradition he believes Silicon Valley is now jeopardizing.
As a gamer, I’m saying this: “It’s crucial to keep them in check, not wreak havoc on an industry that nurtures countless creative minds for centuries. To THR, I express my thoughts about these tech entertainment titans. The U.S. of Amazon, they’ve only dipped their toes into streaming as a marketing strategy. Their main venture? Their cloud and Amazon Prime.
Regarding this matter, it’s unlikely that Hollywood labor leaders would offer a differing opinion. However, they might add that companies like Amazon and Apple are significant employers within the industry as well. Essentially, O’Brien is expressing a concern that remains underdiscussed in industry circles even in 2025: If entertainment isn’t these companies’ primary focus, what will happen when they grow tired of this side venture?
The head of the Teamsters union shares concerns about artificial intelligence and has formed an alliance with Justine Bateman, a vocal opponent of AI. Bateman has spoken highly of him, and even enlisted the Teamsters to support her “No AI” film festival held in Hollywood in March.
O’Brien emphasizes that the danger posed by AI isn’t something in the distant future; it’s an immediate concern we should all be aware of. He points out how our society’s craving for convenience often blinds us to potential repercussions. Autonomous trucks, for instance, are a significant source of worry, but O’Brien insists that he’s equally concerned about the technology being used in film studios.
He suggests that it’s possible to produce a movie using an iPad and develop characters reminiscent of Hollywood productions. However, we need to stay cautious about safeguarding against AI misuse, while also employing AI when beneficial. In situations where AI isn’t necessary, let’s impose restrictions to prevent its use.
However, Trump, who has shown minimal concern about AI regulation to date – even dismantling a Biden executive order that aimed for modest steps in this direction – is an unusual ally in this matter. It’s still puzzling, both within and outside Hollywood, how O’Brien’s focus on human-oriented labor aligns with Trump’s apparent indifference towards the subject.
Other unions associated with Hollywood appear noticeably cool towards Trump. For instance, SAG-AFTRA has refused to readmit the former star of “The Apprentice”, while IATSE has criticized him for allegedly disregarding their picket lines. When major Hollywood unions were asked about O’Brien’s dealings with the White House, only one union responded – the actors’ union. The leader of this union, Duncan Crabtree-Ireland, didn’t directly mention Trump but instead praised the Teamsters as a “strong labor ally” that contributed to the union’s recent strike by showing solidarity and maintaining momentum. Additionally, they noted that O’Brien himself joined the picket lines and motivated SAG-AFTRA members.
Despite the general apprehension, it seems that some, struggling in a shrinking manufacturing sector, might be willing to seek Trump’s aid, albeit with a wrinkled nose. “We do have backing from those other unions,” O’Brien states. “They’re simply not as outspoken.
The uneasy dynamic between Boston residents and the entertainment labor community regarding the Trump influence was clearly demonstrated in an episode of the podcast Better Bad Ideas, released in March, featuring comedian Adam Conover, a WGA West board member. Towards the end of their friendly chat, Conover addressed O’Brien directly about actions taken by the White House that have caused concern among labor leaders, such as layoffs, the closure of DEI programs, and the dismissal of an NLRB board member. “I think we need to be aware that people in power are intentionally making it harder for us to unionize,” Conover asserted to O’Brien.
O’Brien suggested that something destructive might occur, but then surprisingly switched topics to discuss job losses due to Biden’s decision regarding the Keystone Pipeline.
O’Brien can potentially assist Hollywood by participating in domestic productions, especially since the industry is trying to convince Washington Republicans to approve federal tax incentives. However, it remains unclear if O’Brien or anyone else can persuade President Trump to support an industry he often opposes, given his dislike for the governor of the state where Hollywood is based. Some Hollywood insiders are doubtful that O’Brien or Trump’s friend and “special ambassador” Jon Voight will have much impact. Nevertheless, one source claims that O’Brien’s access to the presidency has at least kept Hollywood matters relevant for a president who easily gets distracted.
According to O’Brien, Trump has undergone a transformation in his political stance. “When you campaign on a promise to represent the working class, it’s natural to adjust your policies,” he explains about the president. “I believe he’s benefiting from having better advisors now.” O’Brien suggests that if the administration takes actions perceived as anti-worker, they would be held responsible, although his organization has been relatively quiet on several contentious issues that have sparked concern among other advocates.
O’Brien suggests that his critics may be perplexed due to the uniqueness of his method. “We’re venturing into uncharted territory, something no one else has attempted,” he notes about his approach toward the Trump relationship.
As a devoted admirer, I’d like to share an interesting historical fact: The bond between Teamster leaders and certain Republican presidents isn’t entirely novel. In the 1970s, Jimmy Hoffa’s ally Frank Fitzsimmons enjoyed a close relationship with President Nixon, which translated into some favorable outcomes for the Teamsters. Similarly, IBT boss Jackie Presser played a pivotal role in electing Ronald Reagan in 1980, eventually landing a position on his transition team. It’s worth noting that unlike other labor groups, the Teamsters have often chosen not to adhere strictly to political party lines.
David Witwer, an American Studies professor at Penn State Harrisburg and author of Corruption and Reform in the Teamsters Union, explains that they have historically operated without feeling held back. In other words, they wouldn’t hesitate to act because they perceive that their peers in other unions might not be doing the same thing.
A significant point of interest is how Trump’s influence impacts O’Brien’s relationship with Dougherty, the director of the motion picture division, who has demonstrated socially liberal leanings compared to some past Teamster leaders but remains staunchly loyal to her superior. Notably, she led the union in participating in the Los Angeles Pride parade for the first time, increased diversity within her executive board, and organized a Martin Luther King Jr. celebration. The leadership team of O’Brien’s general executive board is diverse, though controversy arose when his administration dismissed 20 employees from the Teamsters’ organizing department, the majority being people of color. This led to a $2.9 million settlement in a racial discrimination lawsuit; however, the Teamsters maintain they were not at fault, as reported by The Guardian.
Dougherty, who’s known for her daring character, sporting tattoos like one of the late Hoffa, and using explicit language (her popular phrase being “fuck around and find out”), has proven to be not only a valuable ally but also an essential asset for O’Brien.
For over a period of time, Dougherty, a team member at Teamsters and previously a transportation dispatcher on movies like “Transformers: Age of Extinction”, has significantly boosted the visibility of the 6,400-strong Local 399 based in North Hollywood.
During the 2000s, O’Brien, who had met Dougherty through her father who was the secretary-treasurer of a Detroit Teamsters Local, shrewdly invited her to join his political team before the union’s 2021 election. He aimed to contest against the preselected successor of the 23-year incumbent James P. Hoffa, Jimmy’s 80-year-old son, in alliance with Teamsters for a Democratic Union. As an outspoken millennial, Dougherty played a crucial role in strengthening his public image.
I jumped at the opportunity to be part of O’Brien’s 2021 team, as his bold and assertive approach stood out starkly against the complacency I had experienced with past leadership.
In recent times, O’Brien and Dougherty have stirred up the Hollywood labor scene with more assertive statements. O’Brien took things a step further when he arrived prior to Local 399’s contract negotiations in 2024, repeatedly labeling the studios as a “criminal organization operating within white-collar circles.
As a gamer, I’m always questioning if all the noise and drama we create leads to anything meaningful. Critics argue that the 2023 UPS battle didn’t yield as many positive results as O’Brien suggested, leading up to a brutal wave of tens of thousands of job losses due to automation and facility closures. In my eyes, it seems like Sean’s approach is to make loud promises and ultimately deliver less than expected. This is according to John Palmer, a high-ranking Teamsters VP from San Antonio and one of O’Brien’s major critics.
As a gamer, I’d be excited to share my thoughts on the recent UPS contract that over 86% of members approved. This new deal is a game-changer, boosting wages and enhancing working conditions. Frankly, the UPS agreement seems like a winning move! It’s clear that this is a step in the right direction for UPS employees.
Prior to his role of advising Trump about Hollywood, O’Brien was advocating for Hollywood himself. In 2006, he rose to the presidency of Local 25 with a promise to decriminalize the chapter. To dispel the negative perception that Boston was an unsuitable location for filming and that negotiations with producers were complicated by the Teamsters, O’Brien traveled from Boston to Hollywood for a backlot tour. He aimed to assure studios that Massachusetts was not as intimidating as it seemed and that working with producers was straightforward.
The previous leader, George Cashman, admitted guilt in extortion cases following several questionable incidents involving allegations of shakedowns on productions like The Cider House Rules and The Perfect Storm. These events had led to a decline in Hollywood’s interest in Massachusetts during the 2000s.
Sean O’Brien assured Hollywood that the union issues were resolved and such harassment wouldn’t happen again. Although tax incentives spearheaded by former Governor Deval Patrick likely played a significant role, Hollywood eventually came back, producing films like “Surrogates” starring Bruce Willis, Mel Gibson’s “Edge of Darkness”, and Ben Affleck’s “The Town” in the late 2000s. Affleck attributes Boston’s movie resurgence to O’Brien. As the Oscar winner explains to THR, “I believe Sean is significantly responsible for the amount of [Hollywood] work that came to Boston during that time.” He also ensured our production company had a positive experience.
Sean O’Brien told Hollywood that union problems were fixed and they wouldn’t face bullying anymore. This, along with tax incentives led by Governor Deval Patrick, helped Hollywood to return and shoot movies like “Surrogates”, “Edge of Darkness” and “The Town” in Boston during the late 2000s. Ben Affleck thinks O’Brien is responsible for this movie resurgence in Boston because he made sure our film company had a good experience.
During his tenure, O’Brien encountered some turbulence in Hollywood. Approximately five years following the wrap of Town, a Teamsters group disrupted the filming of the popular TV show Top Chef. They aimed to pressure the production into signing union contracts with union drivers instead of local ones, as alleged during subsequent trials. In addition, they reportedly hurled abusive language that was misogynistic, homophobic, and racist towards cast, crew, and a Bravo executive. Four Teamsters were indicted but were later acquitted. O’Brien wasn’t indicted in the matter, but his second-in-command, Mark Harrington, admitted to attempted extortion and served six months of home confinement. However, O’Brien has also had run-ins with union discipline. In 2013, he threatened members who didn’t vote as he desired in a Rhode Island Teamsters election, saying they would be punished. As a result, an independent oversight board for the union suspended him on charges of intimidation.
It seems that Conan O’Brien’s time spent near stages has sharpened his knack for showmanship. He occasionally travels to Southern California to record celebrity episodes of his podcast in a studio in Burbank face-to-face. On the show, O’Brien employs his Boston accent to serve up a blend of jokes and self-deprecating remarks. A recurring topic is guests acknowledging his toughness, a point that O’Brien usually finds amusing while also subtly agreeing. Drawing inspiration from early Joe Rogan, O’Brien invites guests from various political backgrounds, such as Hasan Piker and Ro Khanna, alongside figures like Hawley and Chavez-DeRemer, along with personalities like Casey Affleck and Dana White.
Regardless of his current travels across the nation, O’Brien’s Boston working-class background remains evident. It is rumored that he employs several undercover security personnel. One of these guards might be Daniel Risteen, a former Massachusetts state trooper who made a brief appearance in The Departed. Risteen left the force in 2018 due to two scandals: one involving an altered arrest report for a judge’s daughter and another concerning Risteen’s ex-girlfriend, a trooper who admitted to money laundering and drug trafficking. According to the union’s most recent financial disclosure form, he earned approximately $241,000 in the year 2024.
Years ago, O’Brien almost ventured into television, as friend Mark Wahlberg and his manager Stephen Levinson proposed an unscripted series centered around Teamsters to A&E, highlighting Local 25. The pilot for this show was filmed in 2012; however, the network decided not to air it.
Through his own statements, O’Brien spends a greater amount of time traveling rather than being in D.C., compared to previous Teamster leaders. This undeniably boosts his public image, but it also raises eyebrows among some skeptics who question whether he harbors bigger aspirations in the media or politics.
Currently, it seems that O’Brien is focusing on a different matter: his reelection for the Teamsters in autumn 2026. In April, he unveiled his team, indicating that he will once more be competing alongside his current secretary-treasurer Fred Zuckerman, along with other candidates such as Dougherty.
As a fervent supporter, I’m keeping my eyes peeled for possible contenders aiming to challenge O’Brien, but the Philadelphia Local official, Hooker, is one name that has caught my attention. Hooker, in his own words, is determined to dismantle a climate of “fear, intimidation, retaliation, autocracy, and harassment” within our union, which he alleges O’Brien fosters. Furthermore, O’Brien might find himself questioned about his connections with Trump, whose favor among members could potentially shift over the next year and a half.
Regardless of the outcome of his campaign, O’Brien is confident that time will validate his decision to leave the Democrats and silence those who doubted him.
He stated that it was similar to the concept of madness, isn’t it? We continue to back those who aren’t backing us and receive no benefit in return – this is what he implies about unnamed Democratic politicians. Many Democrats, including their representatives, have moved towards big business, such as Amazon, Apple, Uber, and Lyft. However, we don’t compromise for the sake of conformity. That isn’t our nature.
Rebecca Keegan contributed to this report.
The story you’re reading was published in the July 9 edition of The Hollywood Reporter magazine. Consider subscribing here.
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