Table of Contents
Earlier this month, the New York Times reported that Donald Trump I was considering Brooke Rollins, his former National Policy Council director who now serves as president of a MAGA think tank, the America First Policy Institute, will serve as his chief of staff should he return to the White House.
Within 24 hours, stories emerged. that AFPI (dubbed the “White House in Waiting” for its quiet role in planning a second Trump term) had been hacked by the Chinese.
But within Trump’s inner circle, that wasn’t exactly news: The institute’s online security perimeter had been breached nearly a year earlier, and again earlier this month.
The reason why news was leaked this time? Because, some Trump confidants speculate, someone who didn’t like Rollins wanted it that way.
“Knife fighting is on,” said one. “Someone says, ‘Oh, she wants to be chief of staff?’ Well, you can’t even stop your own organization from being hacked.’”
It’s just one vivid example of the behind-the-scenes maneuvering taking place over a crucial role in the White House even before Trump wins the election. The chief of staff position has always been seen as particularly crucial and particularly fraught for Trump, who went through four chiefs in four years during his first term. Each, despite wildly different styles and personalities, struggled to control Trump and keep him and his administration focused.
Trump himself, those around him say, has been superstitious about planning ahead of a victory and has been reluctant to discuss the matter much. But among those who orbit around the former president, tongues move freely.
A host of insiders see the job as crucial to the potential success of a second Trump administration, and they had a lot to say about the three people most talked about for the job: Rollins, Susie Wiles and Kevin McCarthy.
the favorite
As the de facto campaign manager, Wiles probably has the job if she wants it, nearly everyone insider said. After all, Trump has a history of rewarding those who help him win: He named Republican National Committee chief Reince Priebus as chief and campaign executive director Steve Bannon as chief strategist after his 2016 victory.
But that’s not the only reason people are betting on Wiles, a veteran of Florida politics who grew closer to Trump when he was persona non grata in political circles after January 6.
She is the main reason Trump has a more professional and organized campaign this cycle, experts say. They appreciate his instituted order in an otherwise chaotic political collection and attribute his zero-tolerance policy to slander in favor of an era of relative peace in his orbit.
The most important thing: the boss trusts her. While Trump doesn’t always listen, they have established a relationship in which Wiles can be frank with the former president and tell him when she disagrees, something not many are willing to do in the face of Trump’s occasional temper.
His few detractors argue that Wiles has not had a modern government job. She worked briefly on Capitol Hill for Rep. Jack Kemp (R.N.Y.), as a programmer for Ronald Reagan, and at the Department of Labor before moving to Florida, but Beltway politics have changed considerably since then.
Still, those who have seen Wiles up close say he is a quick learner. Under Trump, he has navigated big egos and elbows, assassination attempts, court cases and convictions. “She’s unflappable,” a source said.
One thing: It’s unclear whether Wiles really wants the job given its grueling nature and how Trump’s previous bosses left. He’s already had a remarkable three-year run at Trump’s side, and people are wondering if he got sick of the personal drama earlier this year after Corey Lewandowski’s sudden return to the campaign.
The political hand
According that Times storyTrump has been asking people’s opinions on Rollins and suggesting she would make “a great chief of staff.” Those who like Rollins say it’s a stark assessment: They argue that she is a political expert who can help pass Trump’s legislative agenda.
But the story has only crystallized opposition to Rollins among many Trump insiders, who believe she has no business having that job, presenting her as a newcomer to Trump’s world whose main attributes are self-promotion and close ties to influencers. AFPI donors. Some worry that it is too close to traditional free-market conservatives and that it clashes with Trump’s embrace of high-tariff “MAGAnomy.”
Still, Rollins has a power base: a Texas native who emerged during Gov. Rick Perry’s administration, grew close to Jared Kushner and ran domestic policy during Trump’s final half-year in office and then gave her exes administration officials a home in AFPI. after the chaotic end of the Trump presidency.
His critics argue that despite his political skills, his political acumen is severely lacking. Some of those who have worked with her think they would eat her alive in the role. The counterpoint is that Trump would not seek re-election and therefore needs someone who can primarily execute his agenda. She is clear-eyed about her political shortcomings, her supporters argue, and could outsource that role. (Notably, he brought Kellyanne Conway to AFPI.)
But what does Trump think? One person told us that Trump praised her profusely and said she could run any business in the country. But he has confronted her in the past over AFPI’s use of his “America First” brand, and the Times reported that he has sought up to $50 million in compensation.
The overthrown speaker
If Wiles has the political chops and Rollins has the political savvy, McCarthy supporters argue the former president has both: “I think there’s an argument for having someone who’s been a legislator,” said one Trump ally, recalling the difficulties that Trump had in 2017 in getting his agenda to Capitol Hill.
Some have questioned whether McCarthy would really accept the job. A former staffer turned legislator, he is now making big money for the first time in his life.
But those who know him best know him best. McCarthy is a hardened political animal who loves to play the inside game. Perhaps no job in Washington would make better use of the relationships he has built over a lifetime in politics. (When asked in the past about his service under Trump, McCarthy said he’s not looking for a job, but wouldn’t rule out taking one.)
In fact, some think McCarthy is also anxious. Two Trump insiders spontaneously pointed out to us that McCarthy’s former consigliere, Jeff Miller, has been pressing for Howard Lutnick, the Cantor Fitzgerald CEO who is also leading the Trump transition, raising questions about Miller’s influence on personnel decisions.
Miller told Playbook that he is not involved: “Howard has been a friend and client for quite some time, but I have no role, official, unofficial or otherwise, in (the) transition.”
As for Trump’s opinion, it is complicated. Trump did little to intervene when MAGA stalwarts moved against McCarthy in the House. Some say he viewed McCarthy as a weak negotiator during his months as president, and remains angry that the Californian did not follow through on his promise to “eliminate” his two impeachments.
Still, the two remain close and talk frequently. Trump appreciates that McCarthy was one of his first allies in Congress. But the opinion among those closest to the former president is that they would be surprised if he gave the job to McCarthy.
Do you like this content? Sign up for POLITICO’s Playbook newsletter.