Earlier this month, The New York Times reported that Donald Trump was contemplating appointing Brooke Rollins — his former Domestic Policy Council director now leading a MAGA think tank, the America First Policy Institute (AFPI) — as his chief of staff if he reclaims the White House.
Within 24 hours, reports surfaced stating that AFPI — referred to as the “White House in waiting” due to its discreet role in planning a potential second Trump term — had been compromised by Chinese hackers.
However, this wasn’t breaking news for those within Trump’s circle: The institute’s cybersecurity had been breached nearly a year ago and again just this month.
The reason this information became public this time? Some of Trump’s confidants speculate that an adversary of Rollins may have leaked it.
“The knife-fighting has begun,” one insider remarked. “Someone’s thinking, ‘Oh, she wants to be chief of staff? Well, she can’t even protect her own organization from being hacked.’”
This scenario exemplifies the intense behind-the-scenes competition for a vital White House position, even before Trump secures the election. The chief of staff position has traditionally been viewed as especially important and particularly contentious for Trump, who cycled through four chiefs in his first term. Each of these chiefs, with vastly different styles and personalities, faced challenges in managing Trump and keeping him and his administration on track.
According to those close to Trump, he has been wary of making plans before achieving victory and has hesitated to delve into the topic. Nevertheless, among his associates, chatter is rampant.
A cadre of insiders considers the chief of staff position pivotal for the success of a potential second Trump administration — and many have strong opinions about the three individuals most frequently mentioned for the role: Rollins, Susie Wiles, and Kevin McCarthy.
The frontrunner
As the unofficial campaign manager, Wiles is likely the top contender for the position, according to nearly all insiders. Trump has a history of rewarding those who help him secure victories — appointing RNC chief Reince Priebus as chief of staff and campaign CEO Steve Bannon as chief strategist after his 2016 success.
However, Wiles is not just a popular choice due to her past contributions; she is a seasoned figure in Florida politics who drew closer to Trump when he became persona non grata in political circles following January 6.
According to insiders, she is a major reason Trump’s current campaign is more structured and efficient. They commend her efforts to impose order upon an otherwise chaotic political landscape and credit her no-tolerance stance on infighting for fostering a period of relative tranquility in their surroundings.
Crucially, she has earned Trump’s trust. While he may not always heed advice, she has established a relationship that allows her to be candid with him and express disagreements — a privilege few possess when faced with Trump’s occasional ire.
Her few critics counter that Wiles lacks experience in modern governmental roles. Although she has briefly worked on the Hill for Rep. Jack Kemp (R-N.Y.), as a scheduler for Ronald Reagan, and in the Labor Department before moving to Florida, the political landscape has dramatically shifted since then.
Nevertheless, those who have closely observed Wiles assert that she is adaptable. Under Trump, she has negotiated big egos, intense rivalries, assassination attempts, legal matters, and convictions. “She’s unflappable,” said one insider.
However, it remains uncertain if Wiles genuinely desires the position, considering its demanding nature and the challenging departures of previous Trump chiefs. Having already enjoyed a remarkable three-year association with Trump, insiders speculate she may be weary of personnel turbulence following Corey Lewandowski’s abrupt return to the campaign earlier this year.
The policy expert
As reported by The Times, Trump has been seeking opinions about Rollins and has suggested she would be “a fantastic chief of staff.” Advocates of Rollins argue that this is a compelling endorsement: they describe her as a sharp policy expert capable of helping advance Trump’s legislative agenda.
However, the report has amplified opposition to Rollins among many in Trump’s inner circle, who believe she is ill-suited for this role. They characterize her as a relatively new figure within Trump’s world, whose primary strengths lie in self-promotion and connections to AFPI’s influential donors. Concerns have been raised that her close ties with traditional free-market conservatives could conflict with Trump’s shift towards tariff-heavy “MAGAnomics.”
On the other hand, Rollins has established a power base: a Texas native who advanced through Gov. Rick Perry’s administration, she grew close to Jared Kushner and led domestic policy during Trump’s last six months in office before providing a platform at AFPI for fellow ex-administration officials following the tumultuous conclusion of Trump’s presidency.
Her skeptics argue that despite her policy expertise, her political savvy is deficient. Some who worked with her believe she would struggle greatly in this position. Yet, supporters argue that Trump’s reelection campaign necessitates someone who can primarily focus on executing his agenda. They contend that she is aware of her political shortcomings and could delegate those responsibilities (notably, she brought Kellyanne Conway to AFPI).
What does Trump think? One source shared that Trump has heaped praise on her, claiming she could manage any business in the country. However, he has also questioned her over AFPI’s appropriation of his “America First” branding, with reports indicating he sought as much as $50 million for its use.
The ousted speaker
If Wiles possesses the political expertise and Rollins has the policy knowledge, proponents of McCarthy argue that the former speaker has a blend of both: “I believe there’s a solid justification for having someone with legislative experience,” remarked one Trump ally, recalling the difficulties Trump faced in 2017 while attempting to pass his agenda through Capitol Hill.
Some have doubted whether McCarthy would accept the role. After years of staff work followed by a lengthy stint as a lawmaker, he is now enjoying considerable financial success for the first time in his career.
However, those familiar with him understand better. McCarthy is a dedicated political strategist who relishes working the inside game. Few positions in Washington could better leverage the relationships he has developed throughout his career. (When previously asked about serving under Trump, McCarthy has stated he is not seeking a position but hasn’t dismissed the idea outright.)
Interestingly, some observers believe McCarthy is too eager. Two Trump associates mentioned, unsolicited, that McCarthy’s longtime advisor Jeff Miller has been advocating for Howard Lutnick, the CEO of Cantor Fitzgerald who is leading Trump’s transition, raising questions about Miller’s influence in personnel decisions.
Miller clarified his position to Playbook, stating he is not involved: “Howard has been a friend and client for quite some time, but I have no role — officially, unofficially or in any capacity whatsoever — in [the] transition.”
As for Trump’s perspective, it’s complex. Trump did not intervene significantly when MAGA loyalists turned against McCarthy in the House. Some suggest he perceived McCarthy as a weak negotiator during his tenure as speaker and remains annoyed that McCarthy did not adhere to a commitment to “expunge” Trump’s dual impeachments.
Nevertheless, they continue to maintain a close relationship and communicate frequently. Trump appreciates that McCarthy was one of his earliest allies in Congress. Still, insiders close to the ex-president believe they would be surprised if he appointed McCarthy for the role.
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