DeSantis Tried to Bury Her. Now She’s Helping Trump Try to Bury Him.

Two months before Election Day 2020, Susie Wiles stood uncomfortably inside a hospitality tent in Florida, caught between two proud and exacting men whom she had helped elect: President Donald J. Trump and Gov. Ron DeSantis.

Mr. DeSantis was not thrilled to see her.

A year earlier, Ms. Wiles had been one of the most powerful people in the Florida governor’s orbit, leading his political operation and plotting his path to national prominence. Then he abruptly banished her, privately questioning her loyalty and moving to blackball her across Republican politics.

So when Mr. Trump and Ms. Wiles, his top Florida adviser, saw the governor inside the tent at a joint event, Mr. Trump proposed a détente.

“Shake hands,” he instructed them, according to two people with direct knowledge of the exchange.

They did not. Both parties looked miserable and said little before walking off.

Less than three years later, Ms. Wiles, 65, has ascended to become perhaps the most significant voice inside Mr. Trump’s third presidential campaign.

Born into celebrity — her father, Pat Summerall, was a famed broadcaster — the attention-shunning Ms. Wiles has worked to send three Republicans to the White House and two to rule Tallahassee over a four-decade career. A key strength, friends say, is negotiating the egos of swaggering Republican men whom she can come to understand almost viscerally.

And she and the rampaging former president suddenly have more in common: They both helped make Ron DeSantis. They would both like to unmake him.

“She knows where the bodies are buried,” said Roger J. Stone Jr., a longtime Trump adviser and expert of political dark arts who has known Ms. Wiles for more than 30 years.

Now, she has become the unwitting embodiment of the conflict between her old boss and her current one, who has not hesitated to state the obvious.

“This guy really hates you!” Mr. Trump has told Ms. Wiles privately, according to a person present, occasionally praising her if she is not in the room: “The only person who ever really had a problem with her is Ron DeSantis.”

Ahead of the 2020 election, Mr. Trump rehired Ms. Wiles, over the governor’s objections, to run his campaign in Florida, as she had in 2016. After his defeat (though not in Florida), Mr. Trump placed her in charge of his post-presidential political affairs.

In many ways, Ms. Wiles’s arc with him mirrors the party’s — the compromises made, the behaviors forgiven — reflecting professional Republicans’ unbridled embrace of a twice-impeached, freshly indicted former president who has lied for more than two years about the last election.

A self-described “card-carrying member of the G.O.P. establishment” when she first joined Mr. Trump’s cause, Ms. Wiles has watched him redefine the term’s very meaning, helping to position him as a pseudo-incumbent in a party he has rebuilt in his image.

Mr. Trump, forever enchanted by television celebrities of a certain era, is also partial to Ms. Wiles’s “good genes,” as he has told people, nodding at Mr. Summerall, whom the former president knew casually.

“Susie is a great and well-respected leader from a wonderful family,” Mr. Trump said in a statement, “and she is also a very smart and tough negotiator!”

Yet Ms. Wiles little resembles the spotlight-seeking, publicly combative Trump aides who have often passed through his upper campaign ranks. She spent much of the 1990s and 2000s working for medium-profile Jacksonville mayors. She is not a television surrogate. She tweets sparingly.

Besides her tenure with Mr. DeSantis — whose allies now insist that Ms. Wiles leaked and influence-peddled at the governor’s expense when she was on his team — she has been the subject of far less internal backbiting than the typical senior Trump adviser. (In conversations with friends, Ms. Wiles, who declined to be interviewed, has furiously denied ever undermining Mr. DeSantis while working for him.)

Those who know Ms. Wiles say she is motivated less by money or fame than by behind-the-scenes recognition that she has sway with the people who matter. She has assumed such unappealing duties as overseeing who gets paid, with a hand that aides have described as tightfisted.

“She’s comfortable being staff and understanding that that’s who she is,” said Newt Gingrich, the former House speaker and an informal Trump adviser. “A lot of people, particularly in the early parts of his presidency, thought their job was to manipulate him.”

The standard caveats about life with Mr. Trump remain immutable: No one can control him in earnest. No position is guaranteed in perpetuity. Ms. Wiles has now survived in his circle more than six years after he first mused, to her face, about firing her.

If Ms. Wiles stops short of the let-Trump-be-Trump creed that has sometimes informed his senior team, neither has she fundamentally changed him or tried.

She has not drastically curtailed his inputs from a constellation of far-right figures and MAGA hangers-on, whose value with the base Ms. Wiles recognizes. (“She has extraordinary judgment,” Mr. Stone said.)

She was managing Mr. Trump’s political operation when he decided to endorse a roster of 2022 candidates who largely underperformed.

She failed to head off Mr. Trump’s dinner in November with Kanye West and an entourage that unexpectedly included Nick Fuentes, an outspoken white supremacist — a gathering that raised questions about what controls were in place around the candidate.

Admirers say navigating Mr. Trump’s volatile impulses is part of the bargain for anyone in Ms. Wiles’s seat — or at least anyone hoping to hang onto it.

And adversaries know enough to fear Mr. Trump’s chances more with Ms. Wiles at his side.

“She’s formidable,” said Charlie Crist, the party-switching former Florida governor who lost a bid for his old office last year as a Democrat.

“She wins,” said John Morgan, a prolific Democratic donor in the state.

“Susie Wiles,” Mr. DeSantis said in his 2018 victory speech, as his wife, Casey, clapped behind him. “Really the best in the business.”

‘She knows when to drop the hammer’

For better and for worse, Ms. Wiles developed an early tolerance for flawed and famous men.

Her father, Mr. Summerall, was a professional football player who later teamed with John Madden to form one of the most successful duos in sports broadcasting history. He was also, by his own account, an alcoholic and often absentee father who credited a letter from Ms. Wiles with eventually getting him to the Betty Ford Center for treatment.

In his 2006 memoir, Mr. Summerall, who died in 2013, described his daughter as someone regularly mortified by his conduct but never compelled to abandon him entirely, recalling his own xenophobic language toward a doctor during a hospitalization. “Susan wanted to crawl under the nearest bedpan and hide,” he wrote.

Raised mostly in New Jersey, Ms. Wiles took an early job as an aide to Jack Kemp, a Republican congressman who had been Mr. Summerall’s teammate. She worked on presidential campaigns for Ronald Reagan and George H.W. Bush.

She forged ties to Republicans locally and nationally, serving in Jacksonville as a district aide to Representative Tillie Fowler but becoming close with Washington fixtures like Paul Manafort, a lobbyist who was later Mr. Trump’s 2016 campaign chairman (and the recipient of a presidential pardon).

After leaving the business for roughly a decade when she had children, Ms. Wiles established herself as one of the party’s go-to strategists in northeastern Florida, alongside her former husband, Lanny Wiles, a veteran Republican advance man.

She developed a reputation for elevating the strengths of her principals, stressing that perceived authenticity could overwhelm many warts. She did so with a down-home delivery that could sometimes be misread, colleagues said.

“It all depends on how you deal with her,” said Tony Fabrizio, a pollster who knew Ms. Wiles before both worked for Mr. Trump. “She knows when to drop the hammer.”

A client’s ideology has not generally been a chief concern. In 2010, Ms. Wiles helped lead Rick Scott’s campaign for Florida governor, throwing in with a Tea Party-era businessman-outsider.

The next year, Ms. Wiles swerved to the establishment-friendly presidential campaign of Jon M. Huntsman Jr., the former Utah governor and Obama administration ambassador to China, briefly managing his run before abruptly leaving.

Ms. Wiles seemed to acknowledge the whiplash when she joined Mr. Trump’s 2016 bid; a top Florida adviser whom Mr. Trump adored, Karen Giorno, was among those who encouraged the campaign to give her a larger role. Ms. Wiles noted in an email at the time that many people thought her support for him “was ill advised — even crazy.”

Yet she seemed to appreciate Mr. Trump’s talents at a microphone and his curated celebrity, appraising his drawbacks as pardonable and politically surmountable.

“I think I can help him,” she said privately.

Ms. Wiles’s presence lent Mr. Trump credibility with old-guard Florida Republicans who might have preferred Jeb Bush or Marco Rubio as their nominee.

Mr. Trump, though, was not initially pleased to have her. Amid a state polling downturn in fall 2016 soon after Ms. Wiles took over in Florida, as Mr. Trump sawed at a steak one night at his Miami golf resort, she was summoned to his table for what amounted to a ritual castigation.

“I don’t think you can do this job,” Mr. Trump told her, tossing off expletives, before turning to others in the room. “Find me somebody else.”

Ms. Wiles replied that if he wanted someone who would set her “hair on fire,” she was indeed the wrong fit. But she maintained that she could help him win.

When Mr. Trump continued to complain, Ms. Wiles eventually left, shaken.

But she did not leave the team. Mr. Trump, more confident as Election Day neared, later told Ms. Wiles that he was sorry they had to have “that little motivational talk,” according to a person familiar with the conversation.

Ms. Wiles rejected the characterization. “We can’t do that again,” she said.

“We won’t have to,” he promised.

An alliance and a rupture with DeSantis

Much of Mr. DeSantis’s 2018 campaign in Florida was premised on Trump emulation: his endorsement, his talking points, a viral ad in which the would-be governor urged his toddler to “build the wall” out of blocks.

So when Mr. DeSantis’s general-election bid sputtered early on, he and Representative Matt Gaetz, a close adviser at the time, determined that another Trump echo was in order. They needed Susie Wiles.

It was an unnatural fit on paper — the sometimes standoffish candidate with few initial ties to Tallahassee and the genial consultant who had helped elect the man he hoped to succeed.

But the two coexisted well enough at first. After Mr. DeSantis edged his Democratic opponent, Andrew Gillum, he asked Ms. Wiles to help steer his transition. Some interviews for administration posts were conducted at her home.

The period represented an inflection point for Ms. Wiles. After 2016, a previous moment of campaign triumph, she did not join Mr. Trump’s White House and kept little contact with him in the years that followed. She remained in Jacksonville, where she had worked since 2011 as a managing partner at Ballard Partners, the prominent lobbying firm run by Brian Ballard, a fund-raiser for Mr. Trump and Mr. DeSantis.

This time, she took a top position in Florida for herself, as chairwoman of Mr. DeSantis’s political committee, charting a course to national exposure for him.

“It is the governor’s desire to fund-raise and maintain a high political profile at all times,” she wrote in a January 2019 memo, “inside and outside of Florida.”

Within months, Mr. DeSantis resolved to achieve these aims without Ms. Wiles.

The reasons given for this have varied. Even more than Mr. Trump, according to people who know both men, the governor and his wife, Casey, his closest adviser, can grow consumed with the idea that associates are trading on his name.

Did Ms. Wiles accept too much credit for his victory? Reward friends and prioritize clients with her expanded power? Speak too freely to reporters, whom Mr. DeSantis reflexively distrusts?

People who have spoken to the governor attributed the breakdown to a combination of such factors, without supplying evidence for the most explosive claims. One ally recalled Mr. DeSantis remarking that staff should remain staff, suggesting that Ms. Wiles had somehow drifted from her allotted lane.

Others have wondered if the governor considered her too close to Mr. Scott, with whom Mr. DeSantis has had a prickly relationship. (In a statement, Mr. Scott called Ms. Wiles “one of the best operatives in the party and a good friend.”)

A spokesman for Mr. DeSantis declined to comment on Ms. Wiles.

In September 2019, the rupture widened into public view. Ms. Wiles’s fund-raising memo, along with other snapshots from inside the governor’s operation, appeared in The Tampa Bay Times.

Ms. Wiles, describing the entire experience to friends as bewildering and bizarre, assured anyone who would listen that she was not the source of a leak that would plainly damage her standing with a boss who prized discretion.

The DeSantises would not hear it. The governor cited the article to others as a final straw.

“It’s her,” he repeated. “It’s her.”

Return to Trumpworld

Immediately, Mr. DeSantis made it known among state power brokers that Mr. Ballard’s firm would lose favor with his office if Ms. Wiles remained there, according to people who spoke with the governor.

Mr. Ballard has denied being strong-armed. Days after the Tampa Bay Times article, Ms. Wiles said she was leaving Ballard Partners “due to a nagging health issue.”

In the insular, gossipy world of Florida politics, her exile was an earthquake. Friends recalled her bordering on despondent in the months afterward.

Mr. DeSantis and Brad Parscale, Mr. Trump’s campaign manager at the time, sought to prevent her from joining his re-election campaign, angering her former Trump colleagues. When Jacksonville was briefly considered as a backup 2020 convention site, Mr. DeSantis was said to discourage donors from aiding the effort to bring the event to his state because Ms. Wiles was advising the planners.

By early summer 2020, after some unsettling Florida presidential polling, Mr. Trump wanted her back. He explained himself in a phone call he initiated with Mr. DeSantis, according to people familiar with the conversation, sounding unmoved as the governor disparaged her.

In July, a Trump campaign Twitter account announced her return with a pledge to “win Florida again going away!”

Mr. Trump did, even if little else went right in November.

While Ms. Wiles was not among those pushing Mr. Trump’s stolen-election fantasies before or after the Jan. 6 riot at the Capitol, neither did she appear to view any of his sins as unforgivable.

As Mr. Trump soured on several aides after his presidency and others left on their own, Ms. Wiles was ultimately brought back, assuming broad responsibility for his political portfolio. Privately, she has signaled a gratitude for his trust in her, particularly after her experience with Mr. DeSantis.

When Mr. Trump declared his candidacy, Ms. Wiles brought in an ally, Brian Jack, to oversee the campaign with her alongside Chris LaCivita, a longtime Republican strategist.

With the governor expected to formally enter the presidential race soon, some DeSantis allies suspect that Ms. Wiles has helped perpetuate a theme in news coverage that he churns through staff and interacts uncomfortably with donors. (Many former aides and even supporters have attested to his disdain for glad-handing.)

But over her past two years beside Mr. Trump, Ms. Wiles’s most notable read on Mr. DeSantis was far simpler.

The former president had sounded incredulous for months that his onetime acolyte would challenge him. Didn’t he remember what Mr. Trump had done for him? Why risk an embarrassing defeat?

Ms. Wiles respectfully disagreed.

“He’s running,” she would tell Mr. Trump. She knew her client.

Kitty Bennett contributed research.