“After all the drama of his first term and the election, everyone was enriching themselves through Trump, and he f**king hates that. It became clear after several people mentioned her name that Susie wouldn’t be like that,” said a person close to Trump.
“Trump world is dynamic and volatile and innovative and ever-changing, and Susie is the rock,” said Florida GOP Rep. Matt Gaetz, who has known Wiles for years.
“The people around him, whether they like Susie or not, all agree that she doesn’t stir up trouble,” said Michael Caputo, a former Trump administration official who is close to both Trump and Wiles.
Wiles’ command of Trump’s post-presidential activities — from his midterm travel and 2022 endorsements
to fundraising through his various committees
— has also landed her praise in Washington, where some Republicans are decidedly less enthusiastic
about the prospect of another White House bid by the former President.
“Susie is a supremely talented woman in a male-dominated arena,” said Republican National Committee Chairwoman Ronna McDaniel. “Her ability to navigate tough political environments to execute campaign goals and deliver Republican victories is unmatched.”
Of course, there is another theory for Wiles’ meteoric rise through the Trump world ranks. 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 unexpectedly competitive 2024 primary against the popular Florida governor
Wiles once served as a top adviser to DeSantis, but she was abruptly ousted from his inner circle in 2019 amid rising tensions between the duo and was then let go from Trump’s campaign operation at the governor’s behest. She was later reinstated.
“I’ve never heard her bash on DeSantis in a ruthless way, but I think she is very aware that he was intimately involved in [her] getting bounced from the 2020 campaign,” said a current Trump adviser.
At the very least, it was enough to create a lasting fissure in their relationship, which several well-placed sources said is virtually nonexistent nowadays. But some believe Wiles’ familiarity with DeSantis — especially his potential weaknesses as a candidate — could also be useful in the future.
“I don’t think President Trump would have won Florida in 2016 without Susie Wiles, and she was instrumental in Ron DeSantis’ victory [as governor] in 2018. They would both benefit from having Susie involved in a 2024 campaign,” said David Bossie, a longtime Trump friend and adviser.
“No doubt” she would be more loyal to Trump in a primary, said Caputo. “She is as steadfast as they come, and I think the President understands that in Susie Wiles, he has competency and loyalty in levels that are very beneficial to him.”
A Trump spokesman and Wiles separately declined to provide comment for this story.
A longtime fixture in Trump world
To be widely respected in Trump’s orbit is no small feat. 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 their former boss
and the last one may be in serious legal jeopardy amid revelations
by the House panel investigating the January 6, 2021, insurrection.
Wiles would never introduce herself as Trump’s chief of staff, preferring to think of herself as a trusted adviser, but nearly everyone in his inner circle sees her as such, including his adult children, according to people familiar with their thinking.
“She’s probably his longest-serving adviser now. Anytime I’ve gone [to see Trump], she’s either there or she’s just left,” said Carlos Trujillo, a Florida-based lobbyist who served as ambassador to the Organization of American States during the Trump administration.
Not a golfer herself, Wiles spends most of her time with Trump huddling in offices at his Bedminster, New Jersey, golf club or Mar-a-Lago resort. People who speak to Trump regularly said he will often pause phone conversations to loop in Wiles, that alone being a supreme testament to her value. Last week, Wiles was seated to the right of Trump during a meeting at Bedminster with Hungarian Prime Minister Viktor Orban, according to a photo posted
by Orban’s spokesman.
“‘It’s always, ‘Let me get Susie in here’ or ‘Make sure you tell Susie about that,'” said Caputo.
But if she needs to get something to Trump without delay, she has been known to make an appearance on the green as well. “She’ll jump in a cart herself and drive down to Trump if she needs to get something in front of him,” said one of the Trump advisers.
Unlike Trump’s previous gatekeepers, Wiles doesn’t closely monitor whom he speaks with, according to several people familiar with the matter. Nor does she actively try to prevent contact with figures on the fringe, these people said. That includes a rotating cast of characters who indulge Trump’s obsession with the 2020 election
or periodically introduce him to far-fledged conspiracy theories of their own. Wiles’ own view of whether the election was stolen is less clear-cut than her boss’, according to multiple people familiar with her thinking.
“I don’t think she believes the election was stolen,” said a person close to Wiles. “She thinks we got beat by … not doing a good enough job of stopping states in the regulatory aspects of the election and that Democrats were smart and ruthless in using the Covid-19 pandemic to their advantage.”
Wiles “carefully rides the tent,” said Caputo. “She has to interact with people who think [the election was stolen], and people who don’t.” Several Trump advisers who were directly involved in organizing the “Stop the Steal” rally on January 6 or who assisted in his efforts to overturn the 2020 election have drawn intense scrutiny from the House select committee
investigating the riot at the US 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 inquiries related to election interference.
Some of those allies are on weekly calls that Wiles holds with Trump’s political team, when she and his coterie of paid advisers discuss primaries on the horizon and how Trump-backed candidates are faring. More recently, she has been involved in conversations about how Trump can best position himself for a third presidential campaign. Wiles “touches everything,” as one Trump adviser described her role.
Over time, these calls have endeared Wiles to the rest of Trump’s team. She will take time to praise aides and advisers by name for contributing savvy ideas and ensures everyone stays up-to-date on Trump’s upcoming travel, said people familiar with the calls. But she will also confront failures head on.
“Susie is so sweet that everybody wants to please her — and maybe that’s part of her shrewdness — but when she has to discipline the motley crew that is Trump world, she doesn’t think twice about it,” said one of the people close to Trump.
Above all, it is Wiles’ competency and the former President’s belief that she isn’t profiting off him that set her apart, according to some of the longest-lasting faces inside Trump’s circle.
As one Democratic strategist in Florida put it: “If I was running for president, I would want Susie Wiles.”
Making her mark in GOP politics
Wiles has built a reputation for delivering hard truths to powerful men. Some of the most difficult words she’s had to share were with her father, the late sportscaster Pat Summerall
, during a 1992 intervention to confront his alcoholism.
“Dad, the few times we’ve been out in public together recently, I’ve been ashamed we shared the same last name,” Wiles said in a letter that was read during the intervention, according to Summerall’s 2006 autobiography. The words made his knees buckle, Summerall wrote. Only after hearing from Wiles did the former NFL kicker and legendary broadcaster agree to enter the Betty Ford Center for treatment.
By then, Wiles had already kick-started a successful path into politics. It wasn’t campus activism, Ronald Reagan, or a seminal moment that drew her in. The hypercompetitive political arena had simply felt like a natural fit for Wiles, who had grown up with two brothers in addition to being the only daughter of a professional athlete. In 1979, she was hired as an assistant for US Rep. Jack Kemp
, an ex-teammate of Summerall’s on the New York Giants. Next, she jumped aboard Reagan’s 1980 presidential campaign as a scheduler.
After a few years in the Reagan administration, Wiles launched a consulting career in her native northeast Florida. She soon became a power player in Duval County, along with her then-husband Lanny Wiles, who was also active in Florida Republican politics (the two later divorced in 2017). There, she ran the district office for US Rep. Tillie Fowler, a Republican, before advising successive Jacksonville mayors, while raising two daughters.
“I have rarely met someone with her instincts for politics and policy and where they intersect,” said John Delaney, the first of those mayors, who leaned on Wiles to sell voters on a multibillion-dollar tax increase to modernize the city. “She knows what to magnify that will resonate with the public.”
After two decades in and around Jacksonville City Hall, Wiles in 2010 was asked to meet with a former health care executive named Rick Scott
. A political novice and awkward public speaker, Scott had launched an eleventh-hour, self-funded GOP bid for Florida governor against state Attorney General Bill McCollum, a heavy favorite with support from most Republicans.
“We told her, ‘Hey, we got a guy nobody knows, we’re behind by 50 points, come join us,'” said Curt Anderson, a top strategist on the Scott campaign. “She was able to immediately come in and bring a level of organization that kept people on task.”
With her candidate’s fortune at her disposal, Wiles engineered an upset over McCollum and the GOP establishment. Scott then managed a narrow victory in the general election
. (He is now the state’s junior US senator
Anderson recalled that before they pulled off Scott’s 2010 win, Republican operatives had warned Wiles and the campaign’s other advisers, “You’ll regret this, and you’ll never work in politics again.” So when Wiles later linked up with Trump — joining a campaign that her peers considered doomed — she was entering familiar territory.
The two first met during a Trump Tower rendezvous 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 primary. Wiles, herself, didn’t come across as a Trump-type. She had helmed the fleeting 2012 presidential campaign of Jon Huntsman
, whose high-road approach to politics was antithetical to Trump, and then helped Mitt Romney
‘s presidential campaign in Florida that year.
Tim Miller, who advised Huntsman’s campaign, said it was “bizarre” to watch Wiles align with Trump.
“We were running a campaign on modernizing the Republican Party, and 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 from the Donald Trump campaign than the Huntsman campaign.”
But Wiles felt the party needed a jolt from the outside. The two clicked, though Trump at first was unconvinced 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 was convinced by advisers in September 2016 to consider adding Wiles to his campaign instead.
“Susie was brought in to run battleground communications for us in a new role as the campaign was expanding,” said Bossie, who was then serving as his deputy campaign manager.
At first, Wiles was not a good fit 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 gray-haired matronly figure,” a source told CNN. “She’s not the one who is plucked out of central casting.”
The tension erupted in the final weeks of the race after a fundraiser at his Doral golf course, when Trump, convinced he was going to lose Florida and blaming his campaign team on the ground, unloaded on Wiles during a late-night meeting, according to three sources with knowledge of the incident. Wiles wondered if she should quit, one source said, and he considered letting her go just 10 days before the election.
“In her words, it was a way she had never been spoken to in her 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 Sunshine State savant. So in 2018, when Trump’s hand-picked choice for Florida governor — DeSantis, then a former congressman — was struggling in the campaign home stretch, Wiles was once again asked to take charge. With her in command, DeSantis eked out a 32,000-vote victory
, the closest election for governor in state history.
Not long after, the problems started.
A public fallout
DeSantis entered office a relative stranger to Tallahassee and the insular world of Florida state government. To guide his transition, he tapped Wiles, who also ran his political operation, and Gaetz, a former state lawmaker before he was elected to Congress and whose father had reigned as a powerful state Senate president. Together, Wiles and Gaetz built DeSantis an administration, interviewing potential department heads from her home in Ponte Vedra Beach, where they killed time watching birds in the estuary off her backyard, Gaetz said.
DeSantis jumped out to a fast start, gaining national attention for his governing style
while raising money at an impressive clip. But behind the scenes, a gulf emerged between him and Wiles. A person close to DeSantis said the governor’s wife, Casey, an influential voice in his orbit, privately questioned whether Wiles was more loyal to Ballard’s lobbying clients, and the couple grew skeptical of the allegiances of people she had hired. They purged staffers they viewed as too close to Wiles and marginalized her role in his political operation.
Then came a revelation, outlined in internal memos 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 privately golf with him or $ 250,000 for an intimate gathering. Wiles had authored one of the memos, which made clear DeSantis and his wife approved the fundraising plan. DeSantis placed the blame on Wiles and cut her out of his circle, though he never explained to her why, a source said.
Trump then removed Wiles from his reelection team at DeSantis’ urging, multiple sources confirmed. She stepped away from Ballard Partners, citing health issues.
In a matter of days, the most successful political operative in Florida was out of work.
“It was tough for 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 remarked in 2019 to a reporter now with CNN: “How do you kick Susie Wiles out of your inner circle if you want to become President of the US?
Wiles remained on the sidelines until the summer of 2020, when Trump saw polling that suggested he was in trouble of losing Florida to Joe Biden
. Several people lobbied for Trump to bring back Wiles, and he began floating the idea in conversations. Bossie tried to get DeSantis onboard, but the governor loudly argued against her rehiring. Meanwhile, Ike Perlmutter, the billionaire Republican donor who owns a home near Mar-a-Lago, sided with DeSantis and strongly pushed Trump to reconsider multiple times, sources familiar with those conversations told CNN. But Trump had made up his mind.
“Trump basically said Susie running his 2020 Florida operation was the right answer. He first asked, ‘What do you think if we do this?’ and then the conversation went to Trump basically saying, ‘We are doing this,'” recalled a source familiar with Trump and Perlmutter’s conversations.
A spokesman for the DeSantis campaign did not respond to a request for comment about the governor’s relationship with Wiles. Several Florida political insiders declined to speak to CNN about the DeSantis-Wiles saga on the record, citing concerns that they or their clients could face retribution from the governor.
Wiles’ return to Florida was a “game-changer,” said one source familiar with operations there. Trump gave her tremendous latitude to run his Florida operation, including resources to target voters who were not traditionally Republican, such as Latinos, school choice parents in the Black community and Jewish residents in Democratic strongholds. In Florida, Democrats traditionally had an advantage during early voting on Sundays, when Black churches organized “Souls to the Polls” voter drives. Trump’s Florida team started “Believers and Ballots” to get White Christians from church to early voting sites and saw strong returns.
One GOP operative in Florida said, “We were the only state that got exactly what we asked for from Trump. And that was all [Wiles].”
In the end, while Trump narrowly lost most swing states, he won Florida
by a healthy 4-point margin.
“She’s like the political Muhammad Ali,” said state Sen. Joe Gruters, chairman of the Florida GOP. “That’s why the President trusts her and works with her on the basis that he has already and probably will in the future.”
A ‘difficult campaign’ ahead
With Trump and DeSantis potentially headed for a 2024 collision
, some Republicans close to both men believe Wiles could be an X factor for Trump. She knows better than most DeSantis’ strengths and where his vulnerabilities lie, and she has developed a deep loyalty to Trump, people close to her say.
Wiles also has a record of unexpected victories she will want to preserve if she accepts a senior role in another Trump campaign, which could be markedly difficult due to his age, mounting legal troubles, and an emerging push by prominent Republican leaders for a crowded GOP primary. Justice Department officials are currently investigating Trump’s actions
leading up to January 6 as part of its criminal probe of efforts to subvert the 2020 election outcome, while there’s a separate investigation in Georgia
into possible criminal meddling in the state’s election results by the former President.
“This will probably be one of her final acts in the political world,” said one of Trump’s advisers.
“It’s going to be a difficult campaign no matter what anybody says,” added Caputo. “[Trump] will need 25 Susie Wiles.”
While some Trump allies fear DeSantis could become another roadblock
to the former President’s quest for a second term, Wiles, in her conversations with people inside Trump’s orbit, has downplayed the role she could play. She is known to say, “You run your race” — a mantra for focusing on your own campaign and not the other team — and is dismissive when asked by allies about the status of her relationship with the Florida governor.
“I’m sure she knows some things that Ron wouldn’t want to have to deal with, but she is smart and knows her credibility is on the line, so she won’t go out there peddling rumor and innuendo,” said one of the people close to Wiles.
Still, Wiles and DeSantis are not on speaking terms. DeSantis will attempt to win reelection
this fall without Wiles on his team, though few expect him to need her.
At Mar-a-Lago, however, Wiles is seen as indispensable. Even in the cutthroat environment Trump has cultivated around him, where unanimity is rare, his closest aides and advisers regard Wiles as a steady hand in one of the most tumultuous periods of his political career.
“Out of all the people who have led his political operation, she has by far done the best job, and I don’t know that it’s particularly close in a lot of ways,” said one of the current Trump advisers.
It would seem, then, that Wiles would be an obvious choice to run Trump’s next campaign should he choose to pursue that path. But the most predictable thing about Trump is that he loves to be unpredictable.
“Would I predict that she would run it? Yes,” said a source close to Trump. “Would it shock me if she got fired tomorrow? No. That’s just Trump world.”