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Sean O’Brien has dogged Amazon at nearly every turn in Boston during the past year, proving to be a formidable nemesis for the retail and logistics behemoth in his hometown.

Now the Teamsters Local 25 president wants to go after Amazon on the national stage. Toward that end, he is crisscrossing the continent in a heated campaign to become president of the International Brotherhood of Teamsters, a job that involves leading nearly 1.4 million members in the United States and Canada. Ballots went out by mail two weeks ago.

O’Brien and his opponent, Steve Vairma, will continue to trade barbs and attempt to win hearts before the voting ends in mid-November. No matter the outcome, it will be historic for the Teamsters. Longtime leader Jim Hoffa is stepping down. A controversial contract with UPS is coming up for renewal. And organizing workers at the ever-growing Amazon tops the to-do list.

Amazon has been a notoriously difficult target for organized labor. The Retail, Wholesale and Department Store Union lost a high-profile vote at a warehouse in Alabama earlier this year, though the result is still being disputed, because of the tactics that the company employed. The Teamsters, meanwhile, has reportedly started membership drives at several locations in Canada, a place that is generally seen as more labor-friendly than the United States.

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Is Amazon unstoppable? O’Brien doesn’t think so. He says labor and government leaders need to ramp up the pressure at the local and national levels. It’s not just to ensure workers get decent pay, working conditions, and benefits, he says. It’s also about leveling the playing field for unionized employers that compete with Amazon — such as UPS, DHL, and Ahold Delhaize.

O’Brien says Local 25 raised an alarm when Amazon sought to use the state-owned Boston Convention & Exhibition Center last year for distributing packages; Amazon was kept at bay. After that, the union persuaded the Boston City Council in December to unanimously pass a resolution saying the company should commit to hiring drivers as direct employees, not independent contractors, and to confer with Local 25 before opening a warehouse or fulfillment center within the city limits.

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The Boston resolution was nonbinding. But the message was clear.

Driven by Local 25′s advocacy, nearly a dozen other municipalities around Boston have since adopted similar measures.

To take the fight nationwide, O’Brien first needs to win this election. O’Brien was once a Hoffa ally. The longtime Teamsters boss had put him in charge of negotiations with UPS, the largest Teamsters employer, at the start of the last round of contract talks. But Hoffa booted him from those talks in 2017 after O’Brien reached out to a rival faction within the union to include more Teamsters in the negotiations.

Vairma, Hoffa’s choice to be his successor, says he has far more experience than O’Brien in the upper levels of union management. O’Brien, he says, has just focused on what’s happening in Massachusetts, while Vairma has embraced a new “Project Amazon” strategy to take on the Seattle-based tech conglomerate across the country.

While declining to disclose the details of this Amazon strategy, Vairma is clear about his overall goal to engage a variety of other unions in this effort, including by rejoining the Teamsters with the AFL-CIO umbrella group.

Vairma, a Denver-based union executive, also paints himself as “the only candidate who hasn’t been suspended from office.” That’s a dig at O’Brien, who faced a two-week suspension from union duties after declaring that opponents of his preferred candidate in a 2013 Rhode Island election should be punished. O’Brien has won over this opposition group, Teamsters for a Democratic Union, as a key supporter in his campaign against Vairma. TDU’s choice in the 2016 race to unseat Hoffa, Fred Zuckerman, is O’Brien’s running mate now.

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Amazon spokeswoman Barbara Agrait says the company does not believe unionization is the best approach to empower workers; Amazon argues that continuous improvement is harder to do nimbly with unions involved, as opposed to direct relationships between managers and employees. The company, she adds, has made great progress with employee pay and safety in recent years and now has an average starting wage of more than $18 an hour, with comprehensive benefits.

Ask labor experts about who poses a bigger threat to Amazon, and they’ll put their money on O’Brien. He is seen as more willing to authorize a strike against an employer and less willing to accept concessions at the bargaining table.

Steve Striffler, director of University of Massachusetts Boston’s Labor Resource Center, says O’Brien and his team represent a more aggressive approach with employers — an attitude Striffler says is necessary if the Teamsters are to prevail against deep-pocketed Amazon.

That’s one reason that John Logan, director of labor and employment studies at San Francisco State University, believes O’Brien will be the likely winner in the election. He says O’Brien has another advantage: his ties to key players in Washington, starting with former Boston mayor Marty Walsh, now President Biden’s secretary of labor.

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O’Brien, a fourth-generation Teamster, has come a long way from hauling heavy equipment for crane operator Shaughnessy & Ahern in South Boston, a job he started soon after graduating from high school. He moved into union administration in the late 1990s. At that time, from his perspective, Amazon was nothing more than a big book club.

Now he’s 49 and in the race of his life. Amazon, he says, has essentially become a global economy. The COVID-19 pandemic accelerated the shift to online commerce, giving Amazon even more clout. The International Brotherhood of Teamsters has missed numerous opportunities to take on Amazon over the years as the company grew bigger, with more resources at its disposal to fight. If O’Brien has his way, the union won’t miss another one.


Jon Chesto can be reached at jon.chesto@globe.com. Follow him on Twitter @jonchesto.