She helped Trump win Florida twice. She now she could lead his campaign for 2024

Oppenheimer: I'm inclined to think Trump will run in 2024 3:15

(CNN) --

Susie Wiles was looking for her next challenge when Donald Trump knocked on her door in the spring.

Planning his comeback after his supporters violently stormed the US Capitol on January 6, 2021, was turning out to be more of a task than the former president expected, so he needed someone to shape it. its chaotic political operation.

Trump, surrounded by advisers who, it seemed to him, had only stayed to enrich themselves, began asking his close friends who would be the person he could entrust with such an unenviable task.

"After all the drama of his first term and the election, the whole world was getting rich off of Trump, and he hates that. After several people mentioned his name, it became clear that Susie would not be like that," he said. a person close to Trump.

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Wiles was an intriguing choice from the start.

A veteran of Trump's presidential campaigns, she had already proven her political mettle twice, helping him to a victory in Florida in 2016 and then increasing his margin of victory there in 2020. Still, it was a curious decision for the former president, obsessed with optics, making his top lieutenant a 64-year-old woman with a hobby of bird-watching and baking cakes, who only asked for her travel expenses to be covered when she accepted the job in March 2021.

But as Trump prepares for his long-awaited 2024 campaign, people from all corners of his orbit, from ardent 2020 election deniers to members of the Republican establishment, say Wiles may be the most sensible choice to run it.

CNN spoke with 16 former and current Trump aides and advisers and those close to Wiles for this report, many of whom described her as the consummate professional, someone who has deftly navigated the factions of Trump's world, the "Mr. las Moscas" without making enemies, earning the respect of both his younger aides at Mar-a-Lago and the dominant personalities in his personal cabinet.

"Trump's world is dynamic and volatile and innovative and ever-changing, and Susie is the rock," said Florida Republican Rep. Matt Gaetz, who has known Wiles for years.

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"The people around her, whether they like Susie or not, they all agree she doesn't make trouble," said Michael Caputo, a former Trump administration official who is close to both Trump and Wiles.

Wiles' mastery of Trump's post-presidential activities, from his midterm trips and 2022 endorsements to fundraising through his various committees, has also earned him praise in Washington, where some Republicans are decidedly less enthusiastic. with the prospect of another run for the White House by the former president.

"Susie is a highly talented woman in a male-dominated arena," said Republican National Committee Chairwoman Ronna McDaniel.

"Her ability of hers to navigate difficult political environments to execute campaign goals and win Republican victories is unmatched."

Of course, there is another theory for Wiles' meteoric rise through the ranks of the Trump world.

Her complicated history with Ron DeSantis has left some Trump allies with the impression that she could be an asset if Trump finds himself in an unexpected and competitive 2024 primary against the popular Florida governor.

Wiles was once a top adviser to DeSantis, but was abruptly ousted from her inner circle in 2019 amid rising tensions between the duo and was later fired from the Trump campaign operation at the governor's behest.

She was later reinstated.

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“I have never heard her lash out at DeSantis in a ruthless way, but I think she is well aware that he was intimately involved in [her] being kicked out of the 2020 campaign,” said a current Trump adviser.

At the very least, it was enough to create a lasting rift in their relationship, which according to several knowledgeable sources is virtually non-existent today.

But some believe Wiles' familiarity with DeSantis, especially his potential weaknesses as a candidate, could also come in handy down the road.

"I don't think President Trump would have won Florida in 2016 without Susie Wiles, and she was instrumental in Ron DeSantis winning [as governor] in 2018. They would both benefit from having Susie involved in a 2024 campaign," David said. Bossie, a longtime friend and adviser to Trump.

"Without a doubt" she would be more loyal to Trump in a primary, Caputo said.

"She's as tough as they come, and I think the president understands that in Susie Wiles, she has competence and loyalty at levels that are very beneficial to him."

A spokesman for Trump and Wiles separately declined to comment for this story.

A person who has been in Trump's world for a long time

Being respected and scandal-free in Trump's orbit is no small thing.

Before Wiles became the former president's de facto chief of staff, four men held the title in some capacity during his presidency.

One was fired via Twitter, two have become high-profile critics of his former boss and the last may be in serious legal jeopardy amid revelations from the House panel investigating the Jan. 6 insurrection. of 2021.

Wiles would never cast herself as Trump's chief of staff, preferring to think of herself as a trusted adviser, but she is seen as such by nearly everyone in her inner circle, including her adult children, according to people familiar with her thinking.

"She's probably the longest-serving adviser. Every time I go [to see Trump], she's there or she just left," said Carlos Trujillo, a Florida-based lobbyist who served as ambassador to Trump. the Organization of American States during the Trump administration.

Wiles, who is not a golfer, spends most of his time with Trump in the offices of his golf club in Bedminster, New Jersey, or at the Mar-a-Lago resort.

People who talk to Trump regularly say he often interrupts phone conversations to get Wiles into action, which is a supreme testament to his courage.

Last week, Wiles sat to Trump's right during a meeting in Bedminster with Hungarian Prime Minister Viktor Orban, according to a photo released by Orban's spokesman.

"It's always, 'Let me bring Susie here,' or 'Make sure you tell Susie about that,'" Caputo said.

But if he needs to get something to Trump without delay, he's been known to make an appearance on the green, too.

"She herself will get in a car and go to Trump if she needs to deliver something to him," said one of Trump's advisers.

Unlike Trump's previous gatekeepers, Wiles doesn't keep a close eye on who he talks to, according to multiple people familiar with the matter.

He also does not actively try to avoid contact with fringe figures, these people said.

That includes a rotating cast of characters who indulge in Trump's obsession with the 2020 election or periodically pitch him with his own conspiracy theories.

Wiles' own opinion on whether the election was stolen is less clear than his boss's, according to multiple people familiar with his thinking.

"I don't think she believes the election was stolen," said a person close to Wiles.

"She believes that we were beaten by ... not doing a good enough job of stopping the states on the regulatory aspects of the election and that the Democrats were smart and ruthless in using the COVID-19 pandemic to their advantage."

Wiles "tread carefully," Caputo said.

"He has to interact with the people who believe [the election was stolen], and the people who don't."

Several Trump advisers who were directly involved in organizing the January 6 "Stop the Steal" rally or who assisted in his efforts to overturn the 2020 election have come under intense scrutiny by the House select committee. Representatives investigating the disturbances at the United States Capitol.

Wiles has not been asked to testify before the panel, a source familiar with the matter told CNN, nor has she been subpoenaed to testify in other ongoing investigations related to election interference.

Some of those allies are in Wiles' weekly calls with Trump's political team, when she and her cabal of paid advisers discuss the primaries on the horizon and how Trump's endorsed candidates are faring.

More recently, she has been involved in conversations about how Trump can best position himself for a third presidential campaign.

Wiles "is in everything," as she described her role as a Trump adviser.

Over time, these calls have endeared Wiles to the rest of the Trump team.

He will take the time to praise aides and advisers by name for contributing smart ideas and make sure everyone is up to date on Trump's upcoming trips, people familiar with the calls said.

But he will also face failures.

"Susie is so sweet that everyone wants to please her - and maybe that's part of her cunning - but when she has to discipline the motley crew that is Trump world, she doesn't think twice," said one of the people. close to Trump.

Above all, what sets her apart is competition from Wiles and the former president's belief that he is not profiting from him, according to some of the older faces within Trump's circle.

As one Florida Democratic strategist put it, "If I were running for president, I'd want Susie Wiles."

Making his mark on Republican Party politics

Wiles has earned a reputation for speaking harsh truths to powerful men.

Some of the hardest words he has ever had to share were with his father, the late sportscaster Pat Summerall, during a 1992 intervention to deal with his alcoholism.

"Dad, the few times we've been out in public together lately, I've been embarrassed that we share the same last name," Wiles said in a letter read during the speech, according to Summerall's 2006 autobiography. her knees would buckle, Summerall wrote.

Only after listening to Wiles did the former NFL kicker and legendary broadcaster agree to check into the Betty Ford Center for treatment.

By then, Wiles had already started a successful path in politics.

It wasn't her college activism, or Ronald Reagan, or a momentous moment of hers that attracted her.

The hyper-competitive arena of politics just seemed second nature to Wiles, who had grown up with two brothers as well as being the only daughter of a professional athlete.

In 1979, she was hired as an assistant to US Representative Jack Kemp, Summerall's former teammate on the New York Giants.

She then joined Reagan's presidential campaign in 1980 as a programmer.

After a few years in the Reagan administration, Wiles began a consulting career in her northeast Florida.

She soon became a powerful actor in Duval County, along with her then-husband Lanny Wiles, who was also active in Florida Republican politics (they later divorced in 2017).

There, she ran the district office of Republican US Rep. Tillie Fowler before advising successive Jacksonville mayors while raising two daughters.

"I have rarely met someone with his flair for politics and laws and where they intersect," said John Delaney, the first of those mayors, who leaned on Wiles to sell voters a multimillion-dollar tax hike to modernize the city. city.

"He knows what to magnify to resonate with the public."

After two decades on City Hall in and around Jacksonville, Wiles was asked in 2010 to meet with a former healthcare executive named Rick Scott.

A political novice and bumbling public speaker, Scott had launched a last-minute, self-funded GOP gubernatorial bid against Florida Attorney General Bill McCollum, a heavy favorite with the support of most Republicans. .

"We told him, 'Hey, we've got a guy nobody knows, we're down 50 points, come join us,'" said Curt Anderson, one of Scott's top campaign strategists.

"She was able to jump right in and bring a level of organization that kept people on task."

With his candidate's fortune at his disposal, Wiles pulled off an upset on McCollum and the GOP establishment.

Scott scored a narrow victory in the general election.

(He is now the state's junior senator.)

Anderson recalled that prior to Scott's victory in 2010, GOP operatives had warned Wiles and the other campaign aides, "You're going to regret this and you're not going to work in politics again."

So when Wiles later joined Trump, in a campaign his teammates considered doomed, he was entering familiar territory.

The two met during a Trump Tower date arranged by Wiles' then-boss, lobbyist and fundraiser Brian Ballard.

At the time, most of Florida's political class had sided with native sons Jeb Bush or Marco Rubio in the GOP presidential primaries.

Wiles herself did not seem like the Trump type.

She had run the short-lived 2012 presidential campaign of Jon Huntsman, whose high-level political approach was antithetical to Trump, and then helped Mitt Romney's presidential campaign in Florida that year.

Tim Miller, who advised the Huntsman campaign, said it was "strange" to see Wiles side with Trump.

"We were campaigning on modernizing the GOP, and we were running on climate change and being decent to immigrants," said Miller, a vocal critic of the GOP's embrace of Trump.

"You can't think of a campaign further removed from Donald Trump's than Huntsman's."

But Wiles felt the match needed a shake-up from the outside.

The two hit it off, though Trump was initially unconvinced that his campaign needed a full-time person in Florida.

That changed after Trump secured the nomination.

Dissatisfied with his top Florida strategist, Karen Giorno, Trump advisers convinced him in September 2016 that he consider bringing Wiles into his campaign.

"Susie was hired to handle battlefield communications as the campaign expanded," said Bossie, then her deputy campaign manager.

At first, Wiles did not fit well with Trump's style.

"He likes someone who can command a room and fit the role he sees in his mind, and here's this grey-haired lady," a source told CNN.

"She is not she who is chosen from the central casting."

The tension erupted in the final weeks of the nomination after a fundraiser at his Doral golf course, when Trump, convinced he was going to lose Florida and blaming his campaign on the ground, took out his anger on Wiles. during a late-night meeting, according to three sources with knowledge of the incident.

Wiles wondered if she should resign, one of the sources said, and he considered letting her go just 10 days before the election.

"In his words, it was a way he had never been spoken to in his life," said a person close to both Wiles and Trump.

But Trump's eventual victory in Florida earned Wiles a reputation as a talented fixer and an expert in the Sunshine State. So in 2018, when Trump's pick for Florida governor, DeSantis, then a former congressman, had difficulties in the final stretch of the campaign, Wiles was once again asked to take charge.

With her at the helm, DeSantis posted a 32,000-vote victory, the closest gubernatorial election in state history.

Shortly after, the problems began.

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DeSantis entered office as a relative unknown in Tallahassee and in the insular world of Florida state government.

To guide his transition, he turned to Wiles, who also ran his political operation, and to Gaetz, a former state legislator before he was elected to Congress whose father had reigned as powerful president of the state Senate.

Together, Wiles and Gaetz built the DeSantis administration, interviewing potential department heads from his Ponte Vedra Beach home, where they would kill time birding in their backyard estuary, Gaetz said.

DeSantis got off to a fast start, gaining national attention for his governing style while raising money at an impressive rate.

But behind the scenes, a chasm arose between him and Wiles.

A person close to DeSantis said the governor's wife, Casey, an influential voice in her orbit, privately questioned whether Wiles was more loyal to Ballard's lobbying clients, and the couple became skeptical of the loyalties of people who had hired.

They purged employees they considered too close to Wiles and marginalized his role in his political operation.

Then came a revelation, outlined in internal communications published by the Tampa Bay Times in September 2019, that DeSantis' political committee had planned to sell access to the governor to donors, including $100,000 to play golf privately with him or $250,000 for an intimate gathering.

Wiles had authored one of the memos, which made it clear that DeSantis and his wife approved of the fundraising plan.

DeSantis blamed Wiles and cut her out of her circle, though he never explained why, according to a source.

Trump then removed Wiles from his re-election team at the urging of DeSantis, multiple sources confirmed.

She walked away from Ballard Partners, citing health problems.

Within days, Florida's most successful political operator was out of a job.

"It was hard on her both personally and professionally," Delaney said.

Caputo, the Trump adviser, called it a "terrible mistake" by DeSantis to let Wiles go.

A source who worked for the governor told a reporter now working for CNN in 2019: "How do you kick Susie Wiles out of your inner circle if you want to be president of the United States?"

Wiles stayed on the sidelines until the summer of 2020, when Trump saw polls suggest he was in trouble losing Florida to Joe Biden.

Several people pushed for Trump to bring Wiles back, and he began to float the idea in the talks.

Bossie tried to get DeSantis on board, but the governor strongly opposed rehiring him.

Meanwhile, Ike Perlmutter, the billionaire Republican donor who owns a home near Mar-a-Lago, sided with DeSantis and heavily lobbied Trump to reconsider multiple times, sources familiar with those conversations told CNN. .

But Trump had made up his mind.

"Trump basically said that Susie running her Florida operation in 2020 was the correct answer. First he asked, 'How about we do this?'

and then the conversation turned to Trump basically saying, 'We're going to do this,'" a source familiar with the Trump-Perlmutter conversations recalled.

A DeSantis campaign spokesman did not respond to a request for comment about the governor's relationship with Wiles.

Several Florida political pundits declined to speak to CNN about the DeSantis-Wiles saga on the record, citing concerns that they or their clients could face retaliation from the governor.

Wiles' return to Florida was a "game changer," said a source familiar with operations there.

Trump gave her enormous latitude to run his Florida operation, including resources to target voters who weren't traditionally Republican, such as Latinos, Black parents and Jewish residents in Democratic strongholds.

In Florida, Democrats traditionally had an advantage during early voting on Sundays, when black churches staged "Souls to the Polls" election campaigns.

Trump's team in Florida launched "Believers and Ballots" to get white church Christians to early voting locations, and it got good results.

A GOP operative in Florida said, "We were the only state that got exactly what we asked for from Trump. And that was it [Wiles]."

In the end, although Trump narrowly lost most of the swing states, he won Florida by a healthy 4-point margin.

"He's like the political Muhammad Ali," said state Sen. Joe Gruters, chairman of the Florida Republican Party.

"That's why the president trusts her and works with her on the basis that he has already done it and probably will do it in the future."

A "difficult campaign" ahead

With Trump and DeSantis potentially headed for a collision in 2024, some Republicans close to both believe Wiles could be an X factor for Trump.

She knows better than most DeSantis' strengths and where her vulnerabilities lie, and has developed a deep loyalty to Trump, people close to her say.

Wiles also has a record of upset victories that he'll want to preserve if he accepts a senior role in another Trump campaign, which could be notoriously difficult given his age, mounting legal troubles, and an emerging push from prominent Republican leaders. for a crowded Republican Party primary.

Justice Department officials are currently investigating Trump's actions leading up to January 6 as part of their criminal probe into efforts to subvert the 2020 election result, while a separate investigation is underway in Georgia into possible meddling. criminal in the state election results by the former president.

"This will probably be one of his last acts in the world of politics," said one of Trump's advisers.

"It's going to be a difficult campaign, whatever they say," added Caputo.

"[Trump] will need 25 Susie Wiles."

While some Trump allies fear DeSantis could become another roadblock in the former president's quest for a second term, Wiles, in his conversations with people close to Trump, has downplayed the governor.

She is known for saying "You run your race", a mantra to focus on your own campaign and not the other team's, and she is dismissive when asked about the status of her relationship with him by her allies. Governor of Florida.

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"I'm sure she knows some things that Ron wouldn't want to have to deal with, but she's smart and knows her credibility is on the line, so she won't go out and peddle rumors and innuendo," said one of those close to Wiles. .

However, Wiles and DeSantis do not speak to each other.

DeSantis will try to win re-election this fall without Wiles on his team, though few expect him to need it.

At Mar-a-Lago, however, Wiles is considered indispensable.

Even in the ruthless environment Trump has cultivated around him, where unanimity is rare, his closest aides and advisers see Wiles as a steady hand in one of the most tumultuous periods of his political career.

"Of all the people who have run her political operation, she's done by far the best job, and I don't know if she's especially close in a lot of ways," said one of Trump's current advisers.

It would seem, then, that Wiles would be an obvious choice to lead Trump's next campaign if he decided to go that route.

But the most predictable thing about Trump is that he loves to be unpredictable.

"Would you predict that he would run it? Yes," said a source close to Trump.

"Would I be surprised if she gets fired tomorrow? No. This is Trump's world."

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