Teamsters President Sean O’Brien’s Not-So-Secret Dream to Take on Amazon, Tesla, and Starbucks

From a Washington Post story by Nick Tabor headlined “Sean O’Brien’s summer of the strike”:

As 8 a.m. brought the end of the night shift at a suburban UPS distribution center, Sean O’Brien stood in the parking lot and sized up two of the men walking out.

Black shorts, black T-shirts, black sneakers. These guys weren’t drivers; they worked inside the warehouse.

A local union official with a graying handlebar mustache beckoned the two men. “How’s it going, guys? Meet Sean O’Brien — general president of the Teamsters union. Come on over! Say hi.”

“How are ya, brotha?” O’Brien said, shaking each hand, his Boston accent coloring every vowel. “You guys preloaders?”

“Yes sir,” said one.

“So you gonna try to be drivers or not?”

The worker started to explain — human resources had taken his application but seemed to be jerking him around. O’Brien listened long enough to get the gist. “A lot of that stuff is subcontracted out now. So just go to your local union. Don’t believe a f—in’ word these people are saying.” O’Brien paused to let this sink in. “There’s a big pandemic goin’ on in there with management,” he continued. “It’s called f—in’ lie-abetes.” Now the workers were grinning. “Ever heard of diabetes? … Well, they got lie-abetes.”

The worker asked for guidance on some shift-scheduling problems. O’Brien advised him to talk to local officials; a national Teamsters leader couldn’t speak to the specifics of each shop. “But get involved with the union,” he urged.

The preloaders may not have recognized him, but the circumstances that brought O’Brien to stake out their workplace — in a prelude to what could be an economy-rattling, history-making strike against UPS this summer — reflects the labor movement’s biggest culture shift in decades.

In 2021, the veteran trucker triumphed in an insurgent campaign to become president of the International Brotherhood of Teamsters, an election marking the end of the Hoffa era. James P. Hoffa, that is, the 82-year-old son of mid-century labor legend Jimmy Hoffa, and a lawyer by training who, rivals like O’Brien believed, lacked his dad’s connection with the average worker and conceded too much for the sake of remaining friendly with employers.

Hot-tempered, profane and ambitious, the 51-year-old O’Brien ran a combative campaign against Hoffa’s endorsed candidate. But he hasn’t stopped running, trying to win hearts and minds in a nation where union enrollment has been declining for decades.

His immediate priority is trying to win more concessions from UPS for its 340,000 Teamster-represented workers — and he seems to relish the prospect of the largest-ever strike against a single U.S. business. On Friday, UPS union members voted by 97 percent to authorize the Teamsters to order a work stoppage as soon as Aug. 1 if contract negotiations haven’t culminated in a deal.

Yet even a UPS strike would serve as a mere testing ground for what could be organized labor’s defining battle of the new century. O’Brien wants to unionize Amazon’s 1 million-plus workers, before the omni-retailer’s culture of hyper-efficiency and gig work — which the Teamsters perceive as a threat to labor aspirations for worker safety, rights and living standards — takes hold permanently in North America.

Some see the fourth-generation Teamster as labor’s long-awaited savior — a 1970s-style scrapper uniquely capable of bringing the movement into the 21st century. O’Brien may not be the spiritual reincarnation of Jimmy Hoffa, but Hoffa could never brag he went viral. Video clips of O’Brien insulting Sen. Markwayne Mullin (R-Okla.), who has owned several businesses, in a March committee hearing were viewed more than a million times within a week.

O’Brien: “We hold greedy CEOs like yourself accountable.”

Mullin: “You calling me a greedy CEO?”

O’Brien: “Oh yeah, you are.”

But some see O’Brien’s old-school sensibilities as a liability. He is seeking to organize a younger generation of workers that chafes at 20th-century managerial tactics, while the Teamsters are still trying to rehabilitate a reputation clouded by the venality and criminality of its mob-linked heyday. Smaller, nimbler unions are competing to organize Amazon’s vast network of supply centers. And O’Brien’s viral moment happened after Mullin attacked him over his $225,000 salary and reputation for “intimidation.”

The senator isn’t alone in that criticism. On the same day O’Brien was sworn in last spring, more than 70 employees — roughly 19 percent of the staff — were abruptly terminated via email, with no severance, and locked out of the Teamsters’ Capitol Hill headquarters. A partial work-from-home policy was eliminated and a dress code enforced. Some employees say they find the new environment stern, uptight and wary.

“If you open up the newspaper, as a Teamster,” said one former employee, who spoke on the condition of anonymity to avoid blowback from O’Brien, “and you saw a company that immediately terminated folks with no notice, no severance, no health care, cutting off your email, you’d say, ‘Holy s—! What kind of an employer is this? There should be a public outcry.’”

O’Brien’s team argues that they had a mandate for sweeping change and that the staff cuts were typical of any political turnover. More broadly, he says, he can’t take on the country’s most powerful retailer without an aggressive approach.

“I’m a conscience, not a bully,” he said. “That’s why they don’t like me.”

O’Brien grew up in the Teamsters the way some people grow up in a church. His father drove trucks, his grandfather drove trucks, his great-grandfather drove trucks. O’Brien could have had a glide path to a white-collar career, thanks to a University of Massachusetts football scholarship, but he dropped out after one semester to haul heavy equipment on construction sites.

“I always wanted to be a Teamstah,” he said.

For O’Brien, union work represented job security and excellent benefits to support a family. “I wanted to buy a home by the time I was 20 years old,” he said. “I bought a home by the time I was 20 years old.” Within two years, he’d become a shop steward. “Here I’m like 22 years old, and grown men with families are coming to me with their problems,” he said. “I’m like, ‘This is great. I can solve problems.’ That was a training day for me.”

In 2006, on the brink of his 34th birthday, he was elected as the principal officer of Boston’s Local 25 — the youngest person ever to run the largest Teamsters chapter in New England. Veteran labor attorney Michael Feinberg, who began representing O’Brien, was stunned by the young man’s charisma and seriousness when he first saw him speak at a Local 25 meeting.

“He had the room,” Feinberg recalled. O’Brien had the “ability to express in his words what the rank-and-file member was thinking but could never formulate.”

For a century, the Teamsters had helped workers leverage their numbers into wages and benefits that ushered their families into the middle class. But the tentacles of organized crime had snaked their way into the union by the 1950s. Even after years of investigations and prosecutions, the mob still polluted the Teamsters image, if not its very culture. Local 25 was associated with Whitey Bulger’s Winter Hill gang well into the 1980s, when O’Brien was a teenager with dreams of trucking. In the ’90s, when he first joined, some members were running a crime ring, robbing banks and armored cars; another member was convicted in a scheme to take bribes from an FBI agent posing as a film producer.

O’Brien acknowledges the Teamsters’ checkered past but bristles when the subject comes up. He argued that politicians and the media exaggerate the union’s misdeeds to undermine its strength.

“There were issues like every other organization,” he said. “I came into this organization concerned about one thing. That was maintaining a career and providing an opportunity for myself and my future family.”

When he took over, O’Brien recognized that an image rehab was in order. Local 25 raised $5 million for charity over the next decade, much of that through an annual fundraising gala for Autism Speaks New England.

But he didn’t achieve his rapid ascent beyond Boston — by 2011, becoming the Teamsters’ eastern region vice president — entirely through charm. O’Brien had a reputation as the guy who would do whatever it took to get his way.

Five of O’Brien’s union associates were indicted for allegedly trying to extort a nonunion production company for “Top Chef: Boston” with tactics such as tire-slashing and bullying behavior. (Four were acquitted; Local 25’s secretary-treasurer pleaded guilty to attempted extortion.) O’Brien himself was suspended for more or less threatening a rival faction of the union, in a speech where he declared that Teamsters for a Democratic Union needed to be “punished” for supposedly trying to “tear down” a Rhode Island local. (He later called it “a poor choice of words.”)

Still, when Hoffa needed a right hand in 2017 to oversee the union’s Package Division as they prepared for contract negotiations with UPS on behalf of the Teamsters’ largest bloc of workers, an aggressive reputation was hardly going to be disqualifying. He tapped the pugnacious young leader from Boston.

Five years later, the Teamsters are gearing up for another negotiation, but this time Hoffa is gone. Now it’s O’Brien’s show.

“If we don’t f—in’ win this campaign,” the new president was telling his staff on an August day in Washington, “we don’t have to worry about ever having a conversation with each other again, because we won’t be here in five years.”

O’Brien now occupies the same mahogany-paneled office once claimed by Hoffa father and son in the Teamsters’ fortresslike headquarters, overlooking the U.S. Senate complex. Legend has it that in the 1950s, an ambitious young staff lawyer on the Senate’s so-called Rackets Committee named Bobby Kennedy looked out his office window in the evenings to see whether Hoffa’s light was still on: He didn’t want to be outworked by his nemesis. Hoffa started keeping the light on overnight.

The 2018 UPS contract negotiations have everything to do with why O’Brien is sitting here now — and how he’s decided to wage the campaign this time.

O’Brien never really clicked with the younger Hoffa, he says. But the partnership ruptured for good when O’Brien proposed adding a leader of Teamsters for a Democratic Union to the negotiating committee. (Hoffa declined to comment for this story.)

O’Brien says now that he was trying to make peace with the administration’s critics and broaden a base of support. But the particular TDU member he turned to was Fred Zuckerman, Hoffa’s unsuccessful challenger for the Teamsters presidency the previous year. Hoffa’s camp saw O’Brien’s outreach as pure betrayal — and in hindsight, they regard it as a political end run. Just months after entrusting O’Brien with the negotiations, Hoffa fired him.

With O’Brien sidelined, the Hoffa administration’s approach to the UPS negotiations backfired spectacularly. In October 2018, workers voted by 54 percent to reject a contract that created a tier of lower-paid, part-time drivers; but Teamsters HQ decided to push it through anyway, invoking a little-used constitutional provision that required a two-thirds majority if less than half the membership voted. Amid the rank-and-file uproar that followed, O’Brien — already campaigning for Hoffa’s job, with Zuckerman as his running mate — saw opportunity. Promising a better contract next time, they defeated Hoffa’s candidate with 67 percent of the vote.

Now, O’Brien is taking nothing for granted. He knows he needs to get this next contract right if he wants to keep his job — and expand the Teamsters’ reach.

It’s the spark for the combative spirit that permeates Teamsters headquarters, where a whiteboard charts a long-term battle plan on a timeline — “practice picketing,” “CAT trainings” (for “contract action teams”), “identify strike teams” … and finally, on the July 31 spot that marks the end of the current contract: “STRIKE.”

Why strike now? As O’Brien himself acknowledged in his Senate testimony, UPS already offers the most plum jobs in the logistics industry, with driver salaries starting at $93,000.

But O’Brien argues that the pandemic gave UPS workers the greatest leverage they’ve had in decades. In 2020, union members risked their health to keep packages moving. UPS’s profits surged and have remained high, with customers still hooked on the online shopping habits they adopted during the lockdowns. “Our members are fed up” and remain convinced, he said, that “the only concern that was being addressed was UPS’s bottom line and their balance sheet.”

No better time, O’Brien reasons, for workers to go to the mats to demand wages beginning at $20 an hour, tighter safety provisions and an end to the two-tier employment system ushered in by the last contract.

A UPS spokesman, Glenn Zaccara, said the company is making “meaningful progress” in the contract negotiations: “UPS has worked collaboratively with the Teamsters for nearly 100 years, and this year is no different. We respect this step in the process and remain committed to making progress at the bargaining table.”

On a grander scale, O’Brien believes organized labor has a once-in-a-generation opportunity to push back against the gig-ification of the American workforce — and he hopes to make this contract into a powerful exhibit of what traditional unions can still offer.

All of this explains O’Brien’s parking-lot charm offensive, where he’s been coaxing members across the country to get more invested in union activities with a friendly display of his workingman bona fides. (“This is how you drive a f—in’ truck, right there,” he told a Teamster in Atlanta, pulling out his phone to show off a recent video of himself operating a tractor-trailer.)

Back at headquarters, O’Brien peppered staff with strategy ideas gleaned from his tour. When he learned that many UPS drivers loathe the cameras the company is installing on some vehicles, he suggested that local officials should emphasize the issue at upcoming rallies. (A company spokesman said that most cameras face outward, not on the driver.) There’s no detail too small for O’Brien, who was especially pleased by a new smartphone app for UPS workers, complete with a built-in “strike savings calculator,” to show how much they need to bank before walking off the job.

He and Zuckerman plan to keep hitting the road every week until August to personally rally the workers.

“We’re not taking vacations,” he said. “I already told my family, ‘I’ll see you around Eastah.’

‘Strike! Strike! Strike!’

The chant filled the ballroom as O’Brien took the stage in Chicago last summer before a crowd of more than 2,000.

Even the emcee at the Labor Notes Conference — a millennial-heavy gathering that aims to strengthen grass-roots ties across disparate unions — seemed taken aback. She had just introduced their next speaker as the man who “pledged that 300,000 Teamsters will strike UPS” when the room erupted in a standing ovation. (She hastened to clarify that a strike would come only if they don’t reach a satisfactory contract.)

“Thank you very much!” O’Brien said. “This is my first time here, and wow — is this an unbelievable crowd!”

He seemed genuinely touched and surprised: A year out, and already his brand as the Guy (Maybe) Striking UPS had caught on with a new generation.

But as he continued his battle cry (“We are gonna put that company on its knees if it needs to happen!”), it was not UPS CEO Carol B. Tomé’s name that he invoked. He launched into a tirade about the “three stooges”: Jeff Bezos, Elon Musk and Howard Schultz, the CEOs of Amazon, Tesla, and Starbucks, respectively. “They are white-collar criminals,” he claimed, hyperbolically, that should be “held accountable” for “the way they treat their workers.”

The crowd booed furiously.

All three billionaires are reliable boogeymen in rooms like these. (Amazon founder Bezos owns The Post. Interim chief executive Patty Stonesifer sits on Amazon’s board.) But Musk’s Tesla and Schultz’s Starbucks are somebody else’s labor fight. O’Brien has made no secret of his hunger to take on Bezos, and Amazon.

With more than 1 million workers, many in modestly paid, highly physical jobs, Amazon is seen as ripe for organization by many in labor. Workers say they have been expected to process as many as 350 items an hour, with mandatory 60-hour weeks during some busy seasons — conditions that some employees say have led to orthopedic injuries or urinary tract infections, because they don’t have time for bathroom breaks. (Amazon spokesperson Mary Kate Paradis said the injury rate across Amazon warehouses has dropped more than 23 percent since 2019. “We’re proud of the progress made by our team and we’ll continue working hard together to keep getting better every day,” she said.)

Yet the jobs come with little security as Amazon increasingly shifts toward gig employment. Thousands of Amazon drivers actually work for third-party companies, subject to being cut without explanation.

But whose place is it to unionize Amazon? In Chicago, O’Brien shared a stage with a younger man with some claim on that turf.

He was Chris Smalls, a New Jersey native and former rapper in his early 30s who had spent five years working in Amazon warehouses. While O’Brien turned out in a traditional navy blazer, Smalls wore dark sunglasses, a clutch of gold chains and a multicolored jacket with EAT THE RICH stitched in yellow thread on the back.

O’Brien has a compelling narrative about coming of age on the same big rigs as his grandfather, but Smalls has what could be the quintessential origin story for the next generation of labor leaders. In March 2020, he led a walkout at a Staten Island warehouse over what he maintained were insufficient covid safety protocols. Terminated that same day, he joined forces with three other Black workers to try to organize the facility.

It was the scrappiest of campaigns, with a bus stop as the base of operations and Smalls living nearby in a tent. Amazon confiscated union fliers and mounted a high-powered anti-union PR blitz. But in March 2022, workers at the facility voted 2,654 to 2,131 to join the fledgling Amazon Labor Union. (An Amazon spokesperson said its employees “have the choice of whether or not to join a union” and that “as a company, we don’t think unions are the best answer for our employees.”)

O’Brien has been quick to praise the ALU. “You can’t take away anything they’ve done,” he told The Washington Post. “Because they’ve been more successful than … anybody, right?” The Teamsters provided meeting space and guidance for the ALU. It was a no-brainer, as O’Brien explains it — of course the Teamsters want every union in the logistics industry to succeed, to force all employers to keep workplace standards as high as possible.

And yet, the dynamics are complicated. Because O’Brien sure would love to see a lot of those 1 million Amazon workers wearing Teamsters jackets one day.

Even while lending the ALU a hand, the Teamsters have been launching their own efforts to organize Amazon workers in Michigan, Pennsylvania and Canada; last month they negotiated a contract for California drivers and dispatchers employed by a third-party Amazon contractor. And yes, O’Brien realizes that winning a strong new contract with UPS would make a fabulous advertisement for the Teamsters as they woo potential members.

Onstage in Chicago, he spoke philosophically about the campaign at hand.

“A victory — whether it’s an election, or once you win an organizing drive — it does not end there,” O’Brien told the audience. “Because in an election, you make a lot of promises. You make a lot of commitments. And you have to deliver on those promises and those commitments.”

He was talking about the UPS battle; but for knowing ears in the room, it also sounded like a subtweet. The ALU’s momentum has slowed; an organizing effort at a second Staten Island warehouse failed. With Amazon’s lawyers throwing up challenges to the initial victory, the ALU may be months or years away from even starting contract negotiations. Smalls’s celebrity — he and fellow ALU leader Derrick Palmer made Time’s “most influential” list of 2022 — has provoked some backlash within the ranks, and employees at other warehouses complain about emails going unanswered when they seek ALU help organizing their own units.

Offstage, O’Brien has been more bluntly skeptical about the ALU’s prospects.

“You can win any f—in’ election, whether it’s an international election, a local election, an organizing drive,” he told The Post. “But you gotta f—in’ deliver at the end of the day. It doesn’t mean s— if they don’t get a contract.”

The Teamsters, meanwhile, are attempting to fight Amazon on a political level that only a million-member dues-paying organization could afford — lobbying the White House to end its federal contracts and packing city council meetings to block construction of new Amazon facilities.

In an interview, Smalls expressed wariness of O’Brien’s intentions, complaining that the Teamsters’ moves could stymie organizing efforts by leaving workers confused over which union to join.

Why not just channel those resources to the ALU, he asked? “The old, established unions don’t want to pass the torch to new efforts,” he said.

Publicly, O’Brien is playing the gracious diplomat. Other labor organizations are circling Amazon: The Retail, Wholesale, and Department Store Union aided attempts to organize an Alabama warehouse, and an independent group called Amazonians United organized warehouses in Sacramento, Chicago and New York. The AFL-CIO says it wants to partner with the Teamsters on its Amazon crusade. Onstage at Labor Notes, O’Brien spoke of unity and collaboration. He saved some of his warmest words for “my man, Chris ‘Big Balls’ Smalls!” and drew big cheers.

When Smalls took the stage, his own calls for solidarity whipped the crowd into even more of a frenzy. “We gotta stay together,” he said. “The labor movement. It’s not just the Amazon Labor Union. It’s not just Chris Smalls and ‘what am I doing.’”

Then Smalls led the room in one of his favorite chants: “F— Jeff Bezos!” O’Brien was wearing a face mask, but it looked like he was joining in.

O’Brien told The Post that week he was ready to help the ALU with whatever they needed: Smalls had his cell number, he said. Smalls, though, still hasn’t called. “We shouldn’t have to ask,” Smalls said. “It should just be given.”

For all his shift-change bonhomie and diplomacy on the dais, O’Brien can be an abrasive force in the office.

“You know, I’m just sick of this,” he declared at the headquarters, half-chiding and half-commiserating with his staff. “I hear all these f—in’ reports about ‘an opportunity here,’ ‘we’re doing this,’ ‘We’re doing that.’ It seems like there’s no f—in’ execution. There’s a lot of f—in’ pressure on the International, and we’re going to do it, no questions asked.”

O’Brien’s problem at that precise moment: the Teamsters were nearing an agreement that would make it easier to unionize as many as 12,000 drivers for the third-largest school bus contractor in America — but with school about to start, why wasn’t his staff putting the squeeze on management now?

Numerous veterans of the Hoffa administration — including two who kept their jobs after the transition layoffs and others who are in touch with current employees — say the office culture is more stifled and less collegial, with staffers afraid to speak out or cross anyone who’s close to the new boss. In May, the board that oversees Teamster elections chided the new administration over its handling of the layoffs, ruling that at least three were actually retaliatory firings of supporters of O’Brien’s opponent.

But other staffers say they find Teamsters headquarters more energized. O’Brien, for his part, sees himself here as he does in general — a man of the people. Last summer, he arranged an office party on the rooftop terrace, where many staffers rarely ventured before. “Some of them have been here 20 years, and they hadn’t even seen the penthouse,” he said.

Later in the meeting, O’Brien hammered his staff on what he saw as a lagging campaign to unionize auto-transport drivers. (“Do you see my frustration? … Am I wrong to have this conversation?”) By the time O’Brien had dictated detailed instructions on whom to call and what to say, his national director of organizing had filled two notebook pages with blue ink.

“Just keep f—in’ following up with these f—in’ people,” O’Brien concluded. “Because at the end of the day? When I gotta blame someone, I wanna make sure I’m blamin’ the right f—in’ person.”

This is the Teamsters in 2023. In the Sean O’Brien era, no one needs to leave their light on overnight to pretend they’re outworking the other guy. With a pair of existential battles on the horizon, the white-collar office culture is no less intense than the scene on any picket line.

“We’re not complaining,” said Lindsay Dougherty, an L.A.-based former film worker elected with O’Brien’s slate as Western region vice president, who now finds herself traveling relentlessly to rallies across 13 states. “We just go — and make sure we have a lot of coffee in us.”

She added: “We all have, like, the Sean O’Brien in us now.”

Nick Tabor is a freelance journalist whose work has appeared in New York Magazine, The New Republic, The Washington Post, Oxford American, The Paris Review, and elsewhere.

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