JPMorgan Chase ( JPM ) CEO Jamie Dimon has been talking regularly to both presidential campaigns in the final stretch of the 2024 contest.
The growing question is whether he will throw his support behind either candidate. The boss of the biggest US bank hinted Tuesday that such a move may be possible.
"I will decide, and I will vote," Dimon said in a Bloomberg Television interview. "I reserve the right to do whatever I want. I'm a citizen. I can vote. I can say what I want. I've never been in the habit of endorsing candidates. But I am thinking through what I want to say or do or something like that."
But whom he might support or whether he will do so at all is far from a foregone conclusion as he sends signals both publicly and privately that have been embraced by both sides.
Dimon’s dialogue with both campaigns is happening on a weekly basis with allies of both candidates, according to people familiar with the talks.
The conversations have included informal and formal advisors to both campaigns, one of these people said, a list that includes both current and former cabinet members.
The tenor of his conversations with the Trump campaign is an agreement on pro-business policies to grow the economy.
It's a level of agreement that Trump's team clearly hopes could lead to more.
Both Dimon and President Trump "share support of commonsense policies like a government efficiency commission that would eliminate fraud and save taxpayer dollars," Trump senior advisor Brian Hughes said in a statement.
But Dimon has also offered public support for key Harris priorities, including new tax credits to lower income Americans.
Dimon has more engagement at the moment with the Harris campaign, one of these people said, as the CEO offers feedback on the Vice President's economic agenda. Dimon has talked with Harris directly within the last three weeks, this person added.
The scrutiny of Dimon's views are intensifying, with a possible endorsement looming as one of the campaign's final most sought after prizes. Just last week Donald Trump’s account even posted a false claim of a Dimon endorsement.
The banker’s eventual retirement as top boss of JPMorgan adds another wrinkle to the intense focus on his actions, as the bank prepares possible successors once Dimon is ready to leave.
A long and complicated relationship with both candidates
The 68-year CEO and executive chairman for JPMorgan holds an outsized sway across Wall Street.
Thus, in addition to a possible endorsement, both campaigns are also eager for his support on their economic narratives.
For instance, Harris could gain support if Dimon says he isn't worried about inflation — while Trump's side would surely prefer him to focus on problems with the economy.
Trump and Dimon also have had a hot-and-cold relationship that stretches back for years.
Trump reportedly courted Dimon for a cabinet role as far back as 2016. When that didn't work out, Trump later claimed the banker "is a poor public speaker & nervous mess."
Just this summer, Trump mentioned Dimon as a possible Treasury Secretary in June before backtracking in July .
Likewise, Dimon encouraged primary season opposition to Trump earlier in this election season but in a January CNBC interview offered kinder words.
"Take a step back, be honest. He was kind of right about NATO, kind of right on immigration," said Dimon. "He grew the economy quite well," he added.
The latest wrinkle came when Trump's Truth Social account posted a false post Friday that claimed an endorsement. The banker's aides quickly shot it down and confirmed it to be false.
Trump sought to distance himself from the post, telling an NBC reporter traveling with him "I don't know anything about it" and adding "somebody put it up."
Yet the false post remains live as of Tuesday evening.
"President Trump often discusses the future of our nation with the best and smartest people, and alongside leaders like Dimon, he will restore America's economy to make life affordable again in a second term," added Hughes of the Trump campaign.
Dimon's relationship with Harris is equally lengthy — and fraught.
In her 2019 autobiography, Harris recounted a tense exchange when she, then California's Attorney General, was helping negotiate a settlement between banks and homeowners who faced foreclosure during the 2008 financial crisis.
"We were like two dogs in a fight," Harris recounted of the phone call with Dimon.
The battle raged over the bank's offer of between $2-4 billion in compensation for California. That offer was eventually raised to $20 billion.
Harris and Dimon appear to have been more cordial as of late. They met for lunch in Washington in March as part of what a person familiar with the discussion then described as Harris's regular outreach to business leaders.
Dimon has also offered support for Harris priorities. The Vice President has made expanding the earned income tax credit for low- to moderate-income workers and families a centerpiece of her economic plan. Dimon has often touted the credit and has called more support there "a no brainer."
Dimon has also offered conditional support for raising taxes on the richest Americans, to align with the so-called "Buffett rule" that the richest Americans shouldn't have an effective tax rate lower than the middle class.
Mr. Dimon's wife, Judy, is also on the record as a Harris supporter. She has donated over a quarter of a million dollars to support the Democratic ticket, according to government records.
Mr. Dimon, meanwhile, has only made a few smaller donations this campaign season totaling about $20,000, those records show. He has also split his money between moderate Democrats like Jon Tester of Montana and conservative Republicans like Joni Ernst of Iowa.
The looming question: Dimon's next step
Further clouding the dynamic and the question of an endorsement in the coming weeks is whether Dimon would be interested in a role in either future administration.
Earlier this year, he offered some indication that the timetable for his retirement may be nearing. It's "not five years anymore," Dimon said in May while speaking at his bank's annual investor day in New York City.
In past years, when asked about the topic, his default response was to say he would stay in the job another five years.
Dimon has also been for years frequently linked to top roles in Washington.
As far back as during President Obama's time in office, Dimon was mentioned as a possible Treasury Secretary. Billionaire Warren Buffett even offered his endorsement in 2012.
This year, Dimon has offered an array of commentary on what direction he'd like to see the campaign take this year but avoided specifics.
During his conversation with Bloomberg this week, Dimon said "I just want to help our government do the right stuff" and offered Dwight Eisenhower as a model president.
"He got the right people there...He never blamed people, he never insulted people," said Dimon adding "it's a more unifying leadership [than] yelling or scream[ing] at each other."
Dimon also published an op-ed with the Washington Post in August, describing in gauzy terms how he hopes the next US president will embrace the concept of unity.
"We live in a perilous time," he wrote. "If we're going to truly unify our country, we need to begin treating opposing views, complaints and critiques as opportunities to find common ground and make us better."
He concluded that if the next president took his advice — no matter who he or she is — they "could be one of our greatest presidents."
David Hollerith is a senior reporter for Yahoo Finance covering banking, crypto, and other areas in finance. Ben Werschkul is Washington correspondent for Yahoo Finance.