Earlier this month, the New York Times reported that Donald Trump was considering Brooke Rollins — his former Domestic Policy Council director now serving as president of a MAGA think tank, the America First Policy Institute — to 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 mapping out a second Trump term — had been hacked by the Chinese.
But inside Trump’s inner circle, that wasn’t exactly news: The institute’s online security perimeter had been breached almost a full year prior, then again earlier this month.
The reason news seeped out this time? Because, some Trump confidants speculate, someone who didn’t like Rollins wanted it to.
“The knife-fighting is underway,” one said. “Someone’s like, ‘Oh, she wants to be chief of staff? Well, she can’t even stop her own organization from getting hacked.’”
It’s just one vivid example of the behind-the-scenes jockeying playing out over a crucial White House role even before Trump wins the election. The chief of staff job has always been seen as particularly crucial and particularly fraught for Trump, who ground through four chiefs in four years during his first term. Each, despite wildly different styles and personalities, struggled to rein in Trump and keep him and his administration focused.
Trump himself, those around him say, has been superstitious about making plans before a victory and has been reluctant to discuss the matter much. But among those orbiting the ex-president, tongues are freely wagging.
A host of insiders view the job as crucial to a potential second Trump administration’s success — and had plenty to say about the three people most discussed for the role: Rollins, Susie Wiles and Kevin McCarthy.
The frontrunner
As de facto campaign manager, Wiles probably has the job if she wants it, almost all of the insiders said. Trump, after all, has a history of rewarding those who help him win — tapping RNC chief Reince Priebus as chief and campaign CEO Steve Bannon as chief strategist following 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 Jan. 6.
She’s the biggest reason why Trump has a more professional and organized campaign this cycle, insiders say. They appreciate her instituting order on an otherwise chaotic political menagerie and credit her zero-tolerance policy on backbiting for an era of relative peace in their orbit.
Most importantly: The boss trusts her. While Trump doesn’t always listen, they’ve established a rapport where Wiles can be frank with the former president and tell him when she disagrees — not something many are willing to do in the face of Trump’s occasional temper.
Her few detractors argue Wiles hasn’t had a modern-day government job. She worked on the Hill briefly for Rep. Jack Kemp (R-N.Y.), as a scheduler for Ronald Reagan and in the Labor Department before decamping to Florida, but Beltway politics have changed considerably since then.
Still, those who’ve seen Wiles up close say she’s a quick study. Under Trump, she’s navigated big egos and sharp elbows, assassination attempts, court cases and convictions. “She’s unflappable,” one insider said.
One thing: It’s unclear if Wiles actually wants the job given its grueling nature and how past Trump chiefs departed. She has already had a remarkable three-year run at Trump’s side, and people wonder if she got her fill of personnel drama earlier this year after Corey Lewandowski’s sudden return to the campaign.
The policy hand
According to that Times story, Trump has been soliciting people’s opinions about Rollins and suggesting she’d make “a great chief of staff.” Those who like Rollins say that’s a sharp assessment: She’s a polished policy hand, they argue, who can help get Trump’s legislative agenda passed.
But the story has only crystallized opposition to Rollins among many Trump insiders, who believe she has no business having that job, casting her as a relative newcomer to Trump world whose main attributes are self-promotion and close ties to AFPI’s influential donors. Some worry she’s too close with traditional free-market conservatives and would clash with Trump’s embrace of tariff-heavy “MAGAnomics.”
Still, Rollins has a power base: A Texas native who came up through Gov. Rick Perry's administration, she grew close to Jared Kushner and helmed domestic policy during Trump’s final half-year in office then gave fellow ex-administration officials a home at AFPI after the chaotic end to Trump’s presidency.
Her critics argue that despite her policy chops, her political acumen is sorely lacking. Some of those who have worked with her believe she’d be eaten alive in the role. The counterpoint is that Trump would not be seeking reelection and thus needs someone who can primarily execute on his agenda. She’s clear-eyed about her political deficiencies, her backers argue, and could outsource that role. (Notably, she brought Kellyanne Conway on at AFPI.)
But what does Trump think? One person told us Trump has lavishly praised her, saying she could run any business in the country. But he’s confronted her in the past over AFPI’s use of his “America First” brand, with the Times reporting he’s sought as much as $50 million in compensation.
The ousted speaker
If Wiles has the political chops and Rollins has the policy know-how, McCarthy backers argue that the former speaker has both: “I think there is an argument to having someone who's been a legislator,” one Trump ally said, harking back to the difficulties Trump had in 2017 getting his agenda across Capitol Hill.
Some have questioned if McCarthy would actually take the job. A longtime-staffer-turned-longtime-lawmaker, he’s now making big money for the first time in his life.
But those who know him best know better. McCarthy is an inveterate political animal who loves playing the inside game. Perhaps no job in Washington would better harness the relationships he’s built over a lifetime in politics. (Asked in the past about serving under Trump, McCarthy has said he’s not angling a job but wouldn’t rule out taking one.)
Some, in fact, think McCarthy is too eager. Two Trump insiders pointed out to us unprompted that McCarthy’s longtime consigliere Jeff Miller has been lobbying for Howard Lutnick, the Cantor Fitzgerald CEO who is also leading Trump’s transition, prompting questions about Miller’s influence on personnel decisions.
Miller told Playbook he isn’t involved: “Howard has been a friend and client for quite a while, but I have no role — officially, unofficially or in any way whatsoever — in [the] transition.”
As for Trump’s view, it’s complicated. Trump didn’t do much to intervene when MAGA die-hards moved against McCarthy in the House. Some say he viewed McCarthy as a weak negotiator during his months as speaker, and he remains vexed that the Californian didn’t make good on a promise to “expunge” his twin impeachments.
Still, the two remain close and talk frequently. Trump appreciates that McCarthy was one of his earliest congressional allies. But the view among those closest to the ex-president is that they’d be surprised if he gave McCarthy the job.
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