Their concerns reflect long-standing gripes about inflation and a rise in illegal immigration that have long dragged on the president’s approval ratings. More recently, however, some have added exhaustion at the various legal proceedings against Trump (not all of which involve the federal government) and dismay over the Biden administration’s flagging support for Israel in the Gaza conflict.

The potential groundswell of deep-pocketed support for Trump could be critical for his campaign, given that its fundraising considerably lags Biden’s. At the same time, any redirection of funds from the Biden campaign could hurt it further, given the president’s political predicament: Many big donors are put off by his softening support for Israel, even as other voters want him to be far tougher on Israel for its invasion of Gaza.

Millionaire and billionaire political donors who are reconsidering Trump include not just longtime Republican boosters returning to back the party’s presumptive nominee but donors like Griffin who steered clear of the former president in his two prior runs for the White House.

In some ways, the well-to-do class isn’t so different from the electorate, as polls have shown Trump leading in the majority of battleground states. Those figures have been largely unchanged since late last year. Also, big-time donors of all political stripes often move to support leading candidates in races.

Big business was hardly part of Trump’s political base in either 2016 or 2020. Corporate leaders came out vociferously in early 2021 against his attempts to interfere with the transfer of power; the largest bank in America, JPMorgan Chase, responded by pausing all political donations, and its CEO, Jamie Dimon, said Trump had been “gassing up a mob.”

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Dimon turned heads across Wall Street in January when he told CNBC from the World Economic Forum in Davos, Switzerland, that Trump had been “kind of right” about a number of issues, including taking a tougher stance toward China and passing tax cuts. The bank’s political action committee, funded by employees including Dimon, has since resumed its giving and handed out more this election cycle to Republicans than to Democrats.

In interviews, other senior Wall Street executives and political donors said they felt that Dimon’s comments had provided cover for them to back Trump more openly.

Dimon declined through a spokesperson to elaborate. A Trump campaign spokesperson did not respond to requests for comment. A Biden campaign spokesperson pointed to the president’s recent fundraising trip to the West Coast, which she said had raised $US10 million from Silicon Valley founders and executives.

There remains a difference between what some prominent businesspeople will say publicly and privately about Trump, who has challenged norms by vowing to investigate political rivals if he is returned to the Oval Office.

Last month, a group of technology heavyweights including Elon Musk, venture capitalist Marc Andreessen and investor Peter Thiel gathered for a dinner during which they discussed how best to oppose a second Biden term, two people briefed on it said. The dinner was reported earlier by the newsletter Puck.

Andreessen, who once said Trump’s immigration plans left him “sick” to his stomach, later told investors from the Middle East that he would not support Biden, one person who was told of the meeting said. That’s further than what Andreessen has said publicly.

A spokesperson for Andreessen declined to comment on those remarks and said he wouldn’t take sides publicly. “Marc talks about current events in casual settings all the time, like every other normal human being,” said the spokesperson, Margit Wennmachers.

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Thiel, one of Trump’s biggest boosters in 2016, has said he does not plan to donate this time around, although he has vented privately about Biden’s management of the economy, according to three people who have spoken with him about the topic. Yet Thiel’s data analytics firm, Palantir Technologies, recently met with a representative of the Trump campaign to discuss the candidate’s potential return to the White House, two people briefed on the sit-down said.

The political environment is also creating some odd bedfellows for Trump. Take Cliff Asness, a billionaire hedge fund manager and self-described libertarian who as recently as this year called the Republican Party a “cult” under the former president.

Last week, after the White House paused an arms shipment to Israel to prevent the weapons from being used in an assault on the tightly populated Gaza city of Rafah, Asness wrote on social platform X that he was “perilously close to the formerly (and still kind of) unthinkable: #TRUMP2024.”

This article originally appeared in The New York Times.