In late September, Donald Trump was in his element, hosting a Sunday dinner at Trump Tower. Surrounded by a few of the wealthiest Republican donors, the former president had little interest in the niceties that typically accompany such gatherings. Hedge fund titan Paul Singer, investment banker Warren Stephens, and Chicago Cubs owner Joe Ricketts all sat around the table, yet the mood was far from cordial.
Instead of expressing gratitude for their past contributions, Trump launched into a frustrated monologue. Between bites of steak, he made it clear that their support wasn’t meeting his expectations. “People need to appreciate me more,” he said angrily, directing his dissatisfaction to those sitting right in front of him.
The episode, first reported by The New York Times, gives a glimpse into the exasperation brewing within Trump’s camp as Election Day draws nearer. Kamala Harris, his Democratic rival, has surged ahead in fundraising, pulling in a staggering billion dollars since replacing Joe Biden on the progressive ticket. And while Trump’s campaign has always leaned heavily on his name and personality, it’s now being seriously outspent on the ground.
Harris’s campaign is using that financial edge to blanket swing states with targeted ads, while Trump struggles to keep pace. She out-raised him by a wide margin over the summer, and that gap isn’t shrinking. For a man who equates money with success, the financial disadvantage is a bitter pill to swallow, and it’s adding to the pressure.
At the Trump Tower dinner, according to The Times, Trump reportedly took swipes at Harris, using a slur to refer to her, and criticized Jewish voters for not backing him despite his pro-Israel policies. He even threw in praise for the tax cuts he had secured, hinting that the donors in the room had directly benefited. The tone was raw, and Trump wasn’t holding back — not even with those whose checks had helped him get this far.
But the donors weren’t exactly rattled. Ricketts, for one, seemed to take it all in stride, commenting afterward that Trump “was in good form.” It’s a sign of how much Trump has shaped the Republican donor class, bending even its wealthiest members to his often abrasive style. They know what they’re signing up for.
However, it’s not just the money — or lack of it — that’s got Trump on edge. He’s feeling stifled by the realities of this campaign, confined to high-dollar dinners instead of holding his signature rallies. The rallies were always where he drew his energy, but security concerns have forced him to cut back. He’s even had to skip out on golf more often than he’d like. “He’s grumbling about how much time he has to spend fundraising,” said one campaign insider, noting that Trump feels boxed in by the endless phone calls and meetings with donors. He sees it all as a distraction from what he truly enjoys — being out on the trail, firing up his supporters, letting loose.
Meanwhile, Harris is running a very different kind of campaign. With her fundraising machine running smoothly, she doesn’t need to spend as much time courting donors. She’s out in swing states like Georgia and Pennsylvania, while Trump has been stuck hosting dinners in places like Texas — where his lead is already secure. At a fundraiser in Los Angeles on the same weekend as Trump’s dinner, Harris raised $28 million. Her team says it’ll likely be her last major fundraising event before the election, a luxury Trump can’t afford.
Trump’s frustration is pushing his campaign to get creative. In some cases, they’ve had to rely on allied groups to cover the costs of his events, a move more typical of an underfunded campaign. Even with massive contributions from the likes of Timothy Mellon, who gave $125 million to pro-Trump super PACs, the money hasn’t stretched far enough.
Trump’s campaign spokeswoman Karoline Leavitt shrugged off concerns about Harris’s financial lead. “If money guaranteed elections, Hillary Clinton would’ve won in 2016.” It’s a line they’ve used before — and one that reflects Trump’s belief that sheer force of personality can still win the day.
Yet behind the bravado, there’s a growing sense of unease. Trump’s team knows that the financial shortfall is hurting them, particularly in critical battleground states where Harris’s campaign is flooding the airwaves. The former president’s increasing agitation and his frequent venting about donor support suggest he understands the stakes. He’s been here before, but this time, the path to victory feels narrower. And while he won’t admit it, the shrinking coffers could be a problem too big even for Trump to bluster his way out of.
