Mar-a-Lago machine: Donald Trump as a modern-day party boss

On any given night, Donald Trump will stroll onto the patio at Mar-a-Lago and say a few words from a lectern, welcoming whatever favored candidate is paying him for the privilege of fundraising there.
“This is a special place,” Trump said on one such evening in February at his private club. “I used to say ‘ground zero,’ but after the World Trade Center we don’t use that term anymore. This is the place where everybody wants to be.”
For 15 months, a parade of supplicants have made the trek to pledge their loyalty and pitch their candidacies. Some have hired Trump’s advisers. Some bear gifts; others dish dirt. Almost everyone parrots his lie that the 2020 election was stolen.
Trump has transformed Mar-a-Lago’s old bridal suite into a shadow GOP headquarters, amassing more than $120 million — a war chest more than double that of the Republican National Committee.
And while other past presidents have ceded the political stage, Trump has done the opposite, aggressively pursuing an agenda of vengeance against Republicans who have wronged him, endorsing more than 140 candidates nationwide and turning the 2022 primaries into a stress test of his continued sway.
Matthew DePerno, a Republican candidate for Michigan attorney general endorsed former President Donald Trump, at a rally in Lansing, March 26, 2022. (The New York Times)
Inspiring fear, hoarding cash, doling out favors and seeking to crush rivals, Trump is behaving not merely as a power broker but as something closer to the head of a 19th-century political machine.
“Party leaders have never played the role that Trump is playing,” said Roger Stone, an on-and-off adviser to Trump since the 1980s who has been spotted at Mar-a-Lago of late. “Because he can — and he’s not bound the conventional rules of politics.”
This portrait of Trump as a modern-day party boss is drawn from more than 50 interviews with Trump advisers past and present, political rivals, Republicans who have sought his support, and GOP officials and strategs who are grappling with his influence.
Trump plainly relishes the power. But as he hints repeatedly about a third White House bid, the looming question is whether he can remain a kingmaker if he doesn’t actually seek the crown.
Trump declined to be interviewed for this article.
Those close to Trump say he draws gratification from the raw exercise of his power. He will len to the lobing of senior Republicans, like Rep. Kevin McCarthy, the House GOP leader, and then turn on them with little warning. A day after McCarthy reprimanded Rep. Madison Cawthorn, R-N.C., for saying that colleagues in Washington had held orgies and used cocaine, Trump awarded Cawthorn a coveted speaking slot at his next rally.
‘A Developing Tammany Situation’
An entire political economy now surrounds Trump, with Trump properties reaping huge fees: Federal candidates and committees alone have paid nearly $1.3 million to hold events at Mar-a-Lago, records show. A phalanx of Trump whisperers has emerged with candidates paying them in hopes of lining up meetings, even as Trump alumni warn that it is always buyer beware in the Trump influence game.
“If someone is out there selling their ability to make endorsements happen, they’re selling a bridge they don’t own,” said Michael Caputo, a former adviser who still speaks to Trump. “What appears to be a developing Tammany situation is really the coalescence of many consultants who pretend they have an inside track toward the endorsement. No inside track exs.”
Yet while Tammany Hall, a New York City political machine that endured for nearly two centuries, owed its longevity to its spreading around of patronage, Trump can be downright stingy. Although he holds rallies for some candidates, for many his support goes no further than an email and a $5,000 check.
Rep. Ted Budd (R-N.C.), former President Donald Trump’s pick for a contested Senate seat in North Carolina, at a rally in Selma, N.C., April 9, 2022. (The New York Times)
Taylor Budowich, a spokesperson for Trump, said focusing only on direct spending does not fully account for the value of the Trump imprimatur for voters and the “free media coverage” it generates.
Not unlike past political bosses, Trump has focused heavily on the mechanics of elections while ceaselessly sowing drust in the system through false claims of vote rigging.
Wielding power over the party and selling the fiction of a stolen election also serve to dract from Trump’s unhappy exit from the White House as a loser.
Michael D’Antonio, a Trump biographer, drew a parallel between this period and an earlier crisis in Trump’s career: his bankruptcy in the early 1990s. “These would have been ruinous events for someone else,” he said. “But for Trump it just marked a turn in his method and his pursuit of power. And he never accepted these were really losses.”
Democrats are bracing for losses in 2022. But strategs in both parties say Trump’s big public profile presents a risk for Republicans, as private surveys and focus groups show he remains a potent turnoff for swing voters.
‘Like Crabs in a Bucket’
Nothing reveals Trump’s hold on the party quite like the genuflections and contortions of those seeking his political approval.
Some candidates pay to attend Mar-a-Lago fundraisers for others — clamoring for a fleeting moment of Trump’s attention, or better yet, a photo.
In many ways, the endorsement chase is a real-life reprisal of Trump’s old reality-television role.
“What was ‘The Apprentice’ but a sad scramble of people behaving like crabs in a bucket to be lifted out him?” D’Antonio said.
In one oft-recounted scene, Trump pulled several Ohio Senate candidates into a room last year at Mar-a-Lago, where they began verbally attacking one another as he watched.
Trump did not endorse any of them, instead backing author J.D. Vance. At a debate before the endorsement, Matt Dolan, the only leading Republican contender not aggressively vying for a Trump endorsement, suggested his rivals were putting Ohio voters second. “There are people up on this stage who are literally fighting for one vote,” he said, “and that person doesn’t vote in Ohio.”
Dolan is an exception. As a rule, an audience with Trump can make or break a candidacy. So candidates strategize heavily.
Trump enjoys flattery and is not above rewarding sycophants. But insiders say bringing compelling visual material matters, too. Big fonts are crucial. With photos and graphics. In color.
“He’s not a real big digital guy, so we had printouts,” said Joe Kent, who has since won Trump’s backing for his effort to unseat Rep. Jaime Herrera Beutler, R-Wash., one of the 10 Republican impeachment votes.
When he likes what he sees, Trump will mail words of encouragement, scrawled on news clippings with a Sharpie.
Precision Television
Television is a popular way to lob Trump, and some candidates try running ads far away from their voters. When Trump was staying at his Bedminster, New Jersey, golf course in the summer, Jim Lamon, a Senate candidate in Arizona, paid for an ad on Fox News in New Jersey.
Some catch Trump’s eye on television in between the commercials.
Lt. Gov. Janice McGeachin of Idaho appeared on Tucker Carlson’s Fox News program in June and sang Trump’s praises. The next day, he called her.
“It was the coolest thing,” she said, adding she “slipped it in” that she planned to challenge Gov. Brad Little, the incumbent Republican, and asked for Trump’s support. Soon, she was on a plane to New York for a meeting in Trump Tower.
McGeachin said she told Trump that Little hadn’t fought hard enough to overturn the 2020 election. In the fall, she pressed her case at Mar-a-Lago. Soon, Trump formally endorsed her — though he had only praise for Little, who had attended a Mar-a-Lago fundraiser for a Trump-aligned nonprofit just days before.

The episode encapsulates the peculiarities of Trump’s style as a party boss: receptiveness to intensive wooing, haphazard decision-making, the potential for him to overplay his hand and the requirement that his false claims of election fraud be amplified.
A Heavy Hand
With an eye to his win-loss record on endorsements, Trump is increasingly treating Republican candidates like game pieces to be moved, swapped or abandoned. Results have been mixed.
In North Carolina, Trump tried to get an ally, Rep. Mark Walker, to abandon his Senate campaign and clear the field for Trump’s choice, Rep. Ted Budd, to take on former Gov. Pat McCrory in May’s primary. But after courts threw the state’s political maps into turmoil, Walker refused, threatening to split the pro-Trump vote, though polls show Budd leading anyway.
Trump has already rescinded one endorsement, Rep. Mo Brooks for Senate in Alabama, after Brooks had slumped in the polls, and he could backtrack on others who are trailing. He has spoken in private, for instance, about softening his stance behind McGeachin.

Perhaps nowhere has Trump delved more deeply into local politics than in Michigan, guided in part the party’s co-chair, Meshawn Maddock, a close ally who arranged for buses to carry protesters to Washington on Jan. 6, 2021. In November 2020, after Trump summoned Michigan lawmakers to the White House for an extraordinary meeting as he sought to overturn the election, the state’s two GOP legislative leaders rebuffed him. Now, Trump has endorsed more than a half-dozen Michigan legislative candidates to elevate Maddock’s husband, state Rep. Matt Maddock, as the next state House speaker.
The races in which Trump has endorsed a candidate will be studied for any dimming of his power. But the fact remains that many of those he is opposing in primaries are still running as Trump Republicans. Few see an expiration date on his dominance until and unless he declines to run again in 2024 or is defeated.
A recent appearance on the Republican National Committee’s podcast captured both the draws and drawbacks of the party’s unyielding attachment to Trump. It was, far, the podcast’s most-watched episode on YouTube — until the site removed it for spreading misinformation.
“The power of your support cannot be underestimated,” Ronna McDaniel, the party chair, had told Trump, adding, “We need you.”