Rumors abound in crazy town.

As the nation braces for upcoming presidential debates — amid mudslinging and name-calling in the wildest political ride in recent history — Donald Trump and Kamala Harris feel the queasiness of anticipation: Whom will America’s largest labor union endorse for president? This question for years didn’t need to be asked as the International Brotherhood of Teamsters has traditionally backed the Democratic Party candidate.

There was a shift in air pressure early in the year when the Teamsters, headed by President Sean O’Brien, donated $45,000 to the Republican National Committee. And despite praising the current leader of the free world as “definitely the most pro-labor president we’ve ever had, and we’ve ever seen,” he didn’t endorse Joe Biden and isn’t quite prepared to endorse Trump or Harris, it would seem.

O’Brien may sense something in the air that could divert his attention to the GOP candidate and has alarmed the Harris/Walz camp by publicly stating, “We have an obligation to do our due diligence” and “not just automatically support one side.” The Teamsters, after all, comprise 1.3 million members, all shades of political stripe.

Teamsters Tough

It was O’Brien who approached Trump to speak at the convention in Milwaukee. He was invited and given a place of prominence in the time frame of speech and audience. The labor guy didn’t pull any punches but made several requests to unify all political sides for union workers. “At the end of the day, the Teamsters are not interested if you have a D, R, or an I next to your name,” O’Brien said during his RNC speech. “We want to know one thing: What are you doing to help American workers?”

The Democratic Party convention apparently had no room at the inn for the chief Teamster or any other representative to speak on behalf of that union’s members. O’Brien took it in stride, joking he “could take it personal, but I honestly think maybe my invitation got lost in the US Postal Service, and next time they should try to ship it [by] UPS, it’ll guarantee delivery.” United Parcel Service is the largest employer in the Teamsters Union.

The DNC had more important people on board to get the Harris train rolling: The Obamas, Clintons, Hollywood types, other billionaires, and lower ranks from battleground states were charged to bring the “joy.”

Hurry Up and Wait

The endorsement of the Teamsters could have a massive impact on how the GOP moves forward. What is significant to the appearance and performance of the union president at the GOP convention is that O’Brien was elected, in part, to reform and reignite the union. Much like Robert F. Kennedy Jr., who declared his independence from the Democratic Party, perhaps O’Brien is seeking a more neutralized ground for pushing his policies and ideals. In recent interviews, he has hinted as much: “You can have whatever opinion you want, but one thing is clear: President Trump is a candidate who’s unafraid to hear from new, loud, and often critical voices.”

The Teamster has his antennae on high alert about 45, telling CNN’s Dana Bash: “No doubt he [Trump] has made some decisions that are not favorable with labor, not favorable with me.” And then immediately pivoted, ensuring that no one could figure out where that important endorsement would land: “But, historically, the union has given money to Democratic candidates, whether it’s Senate or Congress, [who] promised hopes and dreams and never delivered on them.”

He who hesitates might just be weighing the odds of whether he can bring Trump closer to accepting the Protecting the Right to Organize Act — a policy Biden was enthusiastic about and one for which Harris is now leading the charge. Earlier in Detroit, Harris claimed she was all over it: “We who believe in the freedom to organize will pass the PRO Act and put an end to union-busting once and for all.”

But rumors are in full force in lieu of an outright public and official endorsement. Several news outlets claim the Teamsters may sit this election out. That is improbable. Teamsters’ spokesperson Kara Deniz refuted the rumors and added no decisions have been made yet. Deniz also pointed out that the 2024 union process “is the most democratic, inclusive and transparent it’s ever been in our 121-year history – to move this union forward and ensure our members’ voices come first.”

Republican National Committee spokesperson Anna Kelly dropped an inference that Trump, once called a “union buster,” is searching for the middle ground and “is making lasting inroads with union leaders and broadening the Republican tent in a historic way.”

And Deniz hinted further at unity that may ruffle Harris’ feathers. “A lot of our society nowadays, it’s far left, far right, arguments by pundits, opinions formed out the gate. It’s an important point to be able to actually stop and listen and engage with something that we need more of, and [O’Brien] is a firm believer in that.”