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As Boston’s own Sean O’Brien matches UPS at the bargaining table, Amazon could be next

Teamsters showdown with delivery giant could lead to the biggest private-sector strike since the ‘50s — and it’s being led by a labor leader with deep roots in Boston

Teamsters president Sean O'Brien spoke at a rally with UPS workers in Charlestown on April 2, before their national contract negotiations began.Matthew J. Lee/Globe Staff

Sean O’Brien is gearing up for the fight of his life.

The Medford native and fourth generation Teamster knew that resolving the next contract with UPS would be among his first big challenges as president of the International Brotherhood of Teamsters. He worked hard to line up this month’s strike authorization votes, a show of strength backed by 97 percent of the participating members across nearly 180 locals around the country.

The union and the Atlanta-based shipping company have come to terms on dozens of work rules during their talks in Washington, D.C., including a deal that provides for air conditioning in many vehicles. Now comes the hard part: reaching an accord on pay and benefits before the current contract expires on July 31. If that doesn’t happen, O’Brien said, the roughly 340,000 Teamsters members who drive or work in warehouses for UPS will walk off the job. It would be tough for them, tough for the company, and tough for all of us who rely on them to get our packages delivered.

Presumably, no one wants that to happen. But O’Brien said he’d support pulling the trigger — putting the International’s $300 million-plus “strike defense fund” to use — if he doesn’t see adequate financial gains for his membership.


For him, this battle over the largest private-sector union contract in the United States isn’t only about righting the wrongs baked into the union’s current agreement with UPS. It’s meant to show how organized labor can flex its muscle against giant companies. And it’s a prelude for a long-awaited showdown with decidedly anti-union Amazon, where the Teamsters hope to organize the online retail giant’s massive logistics workforce.

“All eyes are upon what the Teamsters do in these negotiations,” O’Brien said in an interview. “It’s going to be the defining moment in the labor movement. It’s going to be a template on how we take on Corporate America, how we take on big business.”


Dissatisfaction with the current UPS contract, signed in 2018, helped O’Brien win his race to lead the Teamsters two years ago. Then the head of the Teamsters Local 25 in Charlestown, O’Brien broke away from the previous International leadership, led by James Hoffa, because of disagreements over the last round of UPS negotiations. In 2018, a majority of voting members rejected the contract terms with UPS, but the Hoffa administration cut a deal with the company to impose it anyway. Of particular concern: the creation of a new tier of drivers, known as “22.4s” (a reference to a contract section), meant to minimize mandatory weekend overtime among regular drivers. The result, though, was to create a new class of lesser-paid drivers. O’Brien wants this two-tier system gone.

A United Parcel Service driver piloted his truck in New York last month. Richard Drew/Associated Press

O’Brien notes that UPS workers were hailed as heroes during the COVID-19 pandemic, as home deliveries became more crucial than ever. UPS, meanwhile, made billions in profits over the past three years, and now, O’Brien said it’s time for the company to share the wealth. It was a theme O’Brien touched on during a Zoom call last week to update members on the negotiations, telling them: “We’re asking for big things [but] the company knows they owe you.”

The starting pay for part-timers is $15.50 an hour — nowhere near what O’Brien wants to see.

“[UPS employees] feel, correctly, they worked crazy hours under unsafe conditions [in the pandemic], during which the company made lots and lots of money,” said Steve Striffler, director of UMass Boston’s Labor Resource Center. “It’s now their time to be paid back. ... There’s a real sense that the rank-and-file are ready for this fight.”


UPS chief executive Carol Tomé told investors in April that she was confident a deal could be reached, and a strike avoided, before the current contract expires. UPS officials continued to express that sentiment after the last of the authorization votes was tallied earlier this month, saying both sides are getting closer to an agreement “that provides wins” for employees, the company, the Teamsters, and customers.

Should Tomé be proven wrong, the resulting strike would be epic in scale.

John Logan, a labor professor at San Francisco State University, said it would probably be the country’s largest private-sector strike since 1959, when a half-million steelworkers walked off the job. Logan counts the 51-year-old O’Brien among a younger generation of labor leaders who aren’t afraid to stand up to corporate interests. It’s a peer group that includes Shawn Fain at the United Auto Workers and Sara Nelson at the Association of Flight Attendants.

“There’s a feeling now, in large sections of the labor movement, that now is the time for bolder, more assertive leadership,” said Logan, who contends that the Teamsters members were eager for someone like O’Brien to take charge.

UPS workers and Teamsters members during a rally outside a UPS hub in the Brooklyn borough of New York on April 21. Paul Frangipane/Bloomberg

O’Brien has breathed new life into the union, Logan added, and has made it clear he won’t accept a lousy deal. One other thing O’Brien has made clear: A strong UPS contract should be the springboard for the Teamsters to go after Amazon.


As head of the union’s Boston local, O’Brien battled Amazon regularly. For example, he said he thwarted the company’s efforts early in the pandemic to use the Boston Convention & Exhibition Center for distributing packages. He also pushed the Boston City Council and similar councils in roughly a dozen other local municipalities to pass nonbinding resolutions urging Amazon to hire drivers as direct employees, not contractors, and to work with Local 25 before opening a local warehouse.

That was well and good in union-friendly Boston. But taking on Amazon on a national scale is a whole other task. Amazon has beat back unionization efforts in places like the Albany area and Alabama. And while warehouse workers famously voted to unionize in Staten Island last year, they don’t yet have a contract to show for it.

For now, O’Brien’s focus is in D.C., where he is trying to secure the best possible deal for his UPS members. But he also has not lost sight of his other big goal: adding Amazon’s hundreds of thousands of blue-collar workers to the International’s 1.2-million-strong membership.

“If we’re going to be successful in organizing Amazon,” O’Brien said, “we need the best contract in the industry [at UPS].”

In other words, the fight is just getting started.

Jon Chesto can be reached at Follow him @jonchesto.