Vice President Kamala Harris’ campaign for re-election in 2024 was marred by an incident involving Teamsters President Sean O’Brien, who revealed that Harris told him she would win the election “with or without you” after a tense meeting on the campaign trail. This moment of arrogance, according to O’Brien, occurred shortly before Harris suffered a significant defeat to Donald Trump.
The meeting between Harris and the Teamsters was set up after President Joe Biden dropped out of the race, and Harris was looking to secure the union’s endorsement for her presidential bid. However, the meeting quickly took a sour turn. O’Brien recounted how Harris agreed to sit down for a roundtable with the union but only answered four out of the 16 questions the Teamsters had prepared. This was in stark contrast to other candidates, like Donald Trump, who answered all the questions the union had for them.
As the meeting progressed, things became increasingly tense. O’Brien recalled that after the fourth question, one of Harris’ staff members slipped him a note informing him that this would be the last question, cutting the meeting short by 20 minutes.
O’Brien was taken aback by this abrupt departure and was left with a memorable line from Harris: “I’m going to win with you or without you.”
The incident stood out not just for the abruptness of Harris’ exit but also for the perceived arrogance of her statement. O’Brien was shocked and mentioned that he immediately contacted Marty Walsh, who had served as Biden’s Secretary of Labor before moving to the NHL Players’ Association. O’Brien said he asked Walsh, “Let me ask you a question, Marty. Excuse my French. Who does this f–king lady think she is?”
The exchange between O’Brien and Harris came at a crucial moment in the election cycle. Harris’ words, along with the union’s decision to withhold its endorsement, signaled a larger dissatisfaction among labor leaders with the Democratic Party. The Teamsters, which represents 1.3 million members, had long been a reliable ally for Democrats, endorsing both the Biden-Harris ticket in 2020 and Hillary Clinton in 2016. However, by 2024, that alliance was visibly fraying.
In fact, weeks before the election, O’Brien made the historic announcement that for the first time since 1996, the Teamsters would not endorse a presidential candidate. This was a significant break from tradition and underscored the growing divide between the Democratic establishment and certain labor groups. O’Brien later revealed that the union’s membership, in a surprising move, overwhelmingly supported Donald Trump over Harris, with 59.6% of Teamsters backing the former president, compared to just 34% for Harris.
O’Brien’s comments also touched on his concerns about President Biden’s ability to continue serving as president due to his age. He remarked that Biden’s decline was evident during their meetings, describing the situation as “kinda sad.” The union leader referred to the plan to run Biden for a second term as “kinda looked like elderly abuse,” further highlighting the concerns about Biden’s fitness for office.
Despite Biden’s struggles, the union had consistently backed the Democratic ticket in recent elections, making their decision to withhold support a strong statement. This shift, combined with the Teamsters’ internal support for Trump, revealed a deeper rift within American labor politics.
The failure to secure the Teamsters’ endorsement was just one of several factors that led to Harris’ crushing loss in the 2024 election. The combination of internal party divisions, dissatisfaction with Biden’s performance, and a lack of support from key unions contributed to a broader sentiment that ultimately saw Trump reclaim the presidency.
As the election results came in, it was clear that Harris’ arrogance had not paid off. Her dismissive attitude toward union leaders and her perceived lack of engagement with the working class played a role in her defeat. The Teamsters’ decision to back Trump, rather than the Democratic candidate, was a clear signal of the changing dynamics in American labor politics.
One of O’Brien’s final remarks captured the sentiment surrounding Harris’ campaign: “The way she treated us—like she didn’t need us—was a big mistake.” This quote underscores the broader frustration many felt with the Harris campaign’s lack of humility and willingness to engage with essential working-class voters.
Kamala Harris’ claim that she would win “with or without” the union’s support seemed to ring hollow as she faced a crushing loss to Donald Trump in the 2024 election. The episode serves as a reminder that political arrogance, especially when it alienates key allies, can have serious consequences on the campaign trail.
