At each gathering, the guest of honor was President Trump. And the people there to celebrate him were some of his wealthiest supporters, who in the case of the hotel fete wrote six-figure checks to hear him crack jokes and discuss his agenda in a rarefied setting.
Even as Trump holds court in large arenas filled with thousands of cheering supporters, he also has been giving rich financiers and business executives up-close access, helping cultivate the kind of big-money outfit he once derided. The effort is intended to boost his favored candidates in this year’s midterms — and to bolster his own reelection prospects.
The money is flowing to America First, an independent operation stocked with former Trump aides that aims to scoop up $100 million through two entities, with the bulk of the funds so far flowing to a nonprofit arm that is not required to disclose the names of its donors.
The chase for wealthy backers is exactly what Donald Trump denounced on the campaign trail in 2016, saying it made candidates “psychologically” beholden to donors and declaring it was “not going to happen with me.”
“Somebody gives them money — not anything wrong — just psychologically when they go to that person, they’re going to do it,” he said in a January 2016 CNN interview. “They owe them.”
But as president, Trump is now immersing himself in that world, wooing figures such as investor and former ambassador Ronald Weiser and Oklahoma oil executive Harold Hamm over New York strip steak and arugula salad.
His allies cast it as a pragmatic move, making the same argument that aides to Democratic presidential nominee Hillary Clinton did when she embraced big-money support in her bid.
“He understands the nature of the political landscape today,” Sean Spicer, former White House spokesman and senior adviser to America First Action, the super PAC, said of Trump. “You can’t unilaterally disarm if the other side is going to utilize super PACs.”
They say it does not conflict with Trump’s oft-repeated pledge to “drain the swamp,” because the rich donors are simply trying to help Trump achieve his aspirations for the country, not get something out of him.
“The donors aren’t D.C. They’re from all over the country, mostly from flyover states,” said Doug Deason, a Dallas investor who is on the finance committee of the America First groups. “They’re looking to get our country back to the states and away from the federal government.”
The White House did not respond to requests for comment.
Among the Trump loyalists who have financially benefited from the effort are former campaign manager Corey Lewandowski and former Milwaukee sheriff David Clarke, who campaigned for Trump.
Their firms, along with ones run by former campaign spokeswoman Katrina Pierson and former campaign digital media director Brad Parscale, all earned at least tens of thousands of dollars each since 2017, the super PAC’s federal filings show.
A firm founded by Marty Obst, an adviser to Vice President Pence, also provided fundraising consulting services. Pence for months zipped across the country as the public face of America First, speaking at rallies and raising millions of dollars at fundraising dinners.
Group officials say America First was modeled as a Trump-focused corollary to Organizing for Action, formed after the 2012 campaign by President Barack Obama’s allies to support his legislative agenda.
America First’s stated goal is to keep GOP control of Congress in 2018 and to get Trump reelected in 2020. But exactly how they’ll get there remains nebulous.
America First groups say they have raised $46.1 million — less than half their goal. The groups have focused their electoral spending on the special elections in Alabama, Pennsylvania and Georgia this cycle.
As for the midterms, America First Action has helped a pro-Trump Republican incumbent in New York fend off a primary challenger. The super PAC says it is holding off on the bulk of its spending, waiting to see how it can complement outside spending from other major GOP groups as November approaches.
Some longtime GOP donors and strategists are skeptical, privately noting that they expected the groups to be more actively fundraising and spending by this point in a midterm election year.
White House officials have privately complained to super PAC officials that there has not been as good a turnout as they wanted at some events, and that some of the prime beneficiaries appear to be Trump loyalists who have left the administration, a White House official said.
They have joked that the super PAC is a “lifestyle PAC,” with large salaries going to “the island of misfit toys,” in the words of one White House official, who spoke on the condition of anonymity to speak candidly about internal discussions.
Meanwhile, America First is drawing a fan club of supporters in the orbits of cable news punditry, social media and former Trump aides and surrogates — united by their adoration of the president and affinity for expressing it on Instagram.
“We don’t have a political director or a policy director. We don’t need one. We’re for everything the president is for, and we’re against everything the president is not,” said Roy W. Bailey, finance chairman of the super PAC.
The two-day Trump hotel event last month in Washington, which included panels and dinner, raised an estimated $5 million for the super PAC, one official said.
Guests paid $100,000 for entry and $250,000 for VIP access to get an insider pitch about the benefits of Trump’s policies from the likes of Treasury Secretary Steven Mnuchin, Rep. Kevin McCarthy (R-Calif.) and Sen. Marco Rubio (R-Fla.).
“This was an amazing event to actually get close to the powerful people who have such an impact, not just in America but the world,” said Dontez Sanders, a real estate investor from Ohio.
According to an attendee, former Arkansas governor Mike Huckabee quipped at dinner that he wanted a Huckabee in the White House and got one: his daughter, press secretary Sarah Huckabee Sanders.
Throughout the two days, the president’s son Donald Trump Jr. shook hands and took photos with donors, who commented that he was an electric speaker like his father.
The events capped off with Trump’s roughly 45-minute, celebratory speech. He was “on fire,” one attendee said, rattling off at least 20 accomplishments from his first 500 days.
He brought champion boxer Evander Holyfield to the stage and gave an “examination” of his famed bitten ear. He thanked individual attendees in the crowd by name, and marveled at the wealth of one of those present.
After the official events ended, guests mingled at the hotel lobby bar, some still wearing their “America First” lanyards.
Andre Soriano, the designer behind “Make America Great Again” gowns, glided through the lobby in a flowy, all-black outfit studded with metal accessories. The ensemble struck a stark contrast with Clarke, the hard-charging sheriff, who chatted with him wearing a suit and white cowboy hat.
“I give so much credit to Donald Trump, who needed this like he needed a hole in the head,” said Charles Gucciardo, a lawyer from New York who attended the dinner. He said he once waited six hours at a Trump event — and then failed — to shake the president’s hand.
“I’ve seen Donald Trump four times so far, but I’ve never gotten to shake his hand,” he lamented. “I just want to shake his hand!”
Josh Dawsey and Anu Narayanswamy contributed to this report.