Hedge fund magnate Paul Singer was so anti-Trump before the 2016 election that he helped bankroll a political action committee dedicated to closing off the reality TV star’s path to the presidency. Trump said at a news conference that there was a “lotta controversy” surrounding the billionaire and attacked Singer’s stance on immigration.

But at the Lotte New York Palace Hotel in midtown this May, Singer amicably chatted with the president and a dozen other high-dollar donors during a fundraiser for Trump’s reelection campaign, according to a person in the room. And he gave $240,000 to the Republican Party this spring shortly before the event.


It was a sign of success for a monthslong charm offensive by the president and his allies toward establishment Republicans who were wary of him during the 2016 campaign.

The president — who claimed in 2016 that he was self-funding his campaign so he couldn’t be “controlled” by donors, even though he ultimately raised most of his funds from outsiders — has developed a new ease with the donor class and is spending significant time away from the White House fundraising from them. Trump has attended eight events for the political groups supporting him in 2018, an uptick from the five he attended the previous year, and he has crisscrossed the country to Los Angeles, Dallas and Columbus, Ohio.

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In closed-door meetings with the megarich he once publicly rebuffed, Trump this spring held relaxed conversations with donors like Singer, who earlier donated to Trump's inaugural committee. He’s tried to soothe their anxieties about his Twitter account and boasted that the media’s criticism doesn’t bother him. Once, Trump veered too far off script and disclosed classified information.

The change in attitude means Trump will be hard-pressed to claim he’s self-funding his 2020 campaign. But his political strategists remain eager for more support from establishment Republican donors, some of whom, like the billionaire Koch brothers, are still wary about donating to the president. Trump allies believe that, given an energized Democratic base, they will need help from potential backers big and small, including those who eschewed him in 2016.

In two weeks, Trump’s power with donors will see its biggest test yet: He'll appear at a two-day fundraiser for America First, the super PAC supporting his agenda, at the Trump International Hotel in Washington. America First initially struggled to raise funds amid staff turnover and competition from other pro-Trump groups, but it now aims to draw contributions from the biggest players in Republican politics. Donors will pay a minimum of $100,000 to attend the event.

Trump’s reelection campaign and the Republican National Committee have amassed huge amounts of money so far. The RNC has $44 million cash on hand to spend on the midterm elections — more than the committee has ever had at this point in a political cycle. Trump, who launched his reelection campaign earlier than any president in history, has accumulated $28 million a full 2½ years ahead of his reelection.

The White House declined to comment for this story, which is based on interviews with Trump operatives and fundraisers directly involved with the efforts to build relationships with donors and attendees at recent fundraising events.

Last week, Trump’s travels took him across the country and back two times, once to Tennessee, where he hosted a rally and attended a fundraiser for Republican Senate candidate Marsha Blackburn, and to Texas for fundraising stops in Houston and Dallas. On three other occasions, the president — who rarely steps out of the White House during his evenings in Washington — joined small groups of donors to America First for dinners around the district hosted by supporters such as lawyer C. Boyden Gray.

The events have not all gone smoothly. At a recent event in New York, Trump boasted about a classified clash between U.S. troops and Russian mercenaries in Syria. A Chinese bank tried to sell tickets to a May 31 dinner in Dallas, which could constitute a violation of election law. And the Associated Press reported that former RNC fundraising vice chair Elliott Broidy helped arrange a photo of the president with a man who had been convicted of sexually abusing children. Broidy stepped down from the RNC in April after news reports that Trump attorney Michael Cohen had negotiated a $1.6 million payoff to a Playboy Playmate on Broidy’s behalf.

In Texas, where Trump has attended three fundraisers in the past year, some longtime supporters of the Bush family have yet to donate to pro-Trump causes or have only recently come around. Trump once called Jeb Bush, who he faced in the Republican presidential primaries, a “puppet” to his donors.

Several Texas billionaires with a long track record of giving to Republican politics — such as Kinder Morgan CEO Richard Kinder — have not donated to the Trump campaign or the RNC since he became president.

“There was a lot of loyalty towards the Bush family,” said Gaylord Hughey, a sought-after East Texas bundler who originally supported Bush during the presidential election before fundraising for Trump. “These are hard-fought battles, and sometimes it just takes a while for people to get to know, accept and trust what they viewed as the opposition.”

Last week, Trump charmed the moneyed Texas political class that funded Bush’s presidential run. The president pontificated about negotiating with North Korea and reviewed his accomplishments as supporters asked questions and ate lobster and steak.

"He’s so great from a retail perspective. He overdelivers. I think major donors are getting beyond their expectations," said Texas financier Roy Bailey, who served as a co-chairman of Trump’s national finance committee during the 2016 elections and is now fundraising for America First.

Trump could use more such donors. Most of the funds raised by his campaign and the RNC still come from people who give $200 or less. That’s a point of pride because it shows grass-roots support, but it’s also an expensive way to raise money. The RNC spends millions of dollars each year on postage alone to mail out requests for $25 and $50 contributions.

Six-figure contributions to the RNC, meanwhile, come with strings attached: much of its cash legally must go toward categories such as building maintenance and legal fees, not political activities. As of February, about a third of the RNC’s funds were tied up in those accounts.

Trump also needs to widen his donor pool for his reelection campaign. Because he launched his campaign so early, bigger donors could max out well before 2020. Two-thirds of the donors contributing $200 or more who have given money to the joint fundraising committee formed by Trump and the RNC for large contributions have already given the maximum amount for the 2020 primaries, according to a POLITICO analysis of disclosure records. And smaller donors could tire of frequent requests for cash.

And not every Trump donor is an unequivocal fan of the president.

“Is every tweet that he makes one that we’re enthusiastic about? No,” said retired Los Angeles investor Thomas Wachtell, who saw Trump at the Beverly Hills home of Tampa Bay Buccaneers owner Edward Glazer in March.

There, Trump fielded an hour of questions on policy issues such as a “Right to Try” pharmaceutical bill then moving through Congress. Around 60 guests attended, each of whom paid between $35,000 and $250,000 for the event.

“It was a superb performance of somebody who was enjoying his job, who knew what he was doing, and who was comfortable in his own skin. It was unexpected,” Wachtell said. “He had fun that night.”

-- Alex Isenstadt contributed to this report.

