ArcaMax

Susie Wiles has a reputation. Ask anyone in Washington and words like “strategic,” “disciplined,” and “skilled” come up. She’s widely held to be one of the most effective tacticians in modern politics.

She’s also known for her low-key, low-drama energy, preferring to remain behind-the-scenes as opposed to preening for cameras like so many other figures in President Trump’s orbit.

Trump’s nickname for his chief of staff is “The Ice Maiden,” referring to her coolheaded nature. The former mayor of Jacksonville said Wiles is “a political savant” who possesses “just otherworldly sort of political instincts.” She herself has said her specialty is “creating order from chaos.”

So, how the hell did a two-part, 11-interview Vanity Fair exposé, in which Wiles unabashedly and recklessly critiques members of Trump’s inner circle, contradicts Trump himself, and reveals some truly stunning behind-the-scenes details — on the record — come to be?

The astonishing set of interviews writer Chris Whipple conducted with Wiles over months has rocked Washington, sent Trump’s comms shop into hyperdrive, and has everyone wondering how Wiles, such a political pro, let this even happen.

Is she sabotaging him? Is she trying to get out and in the most explosive way possible? Is she using the press to force some course-correction inside the White House?

I suspect the explanation is far more simple and less sinister: ego.

For one, it’s hard to say no when a glossy outlet like Vanity Fair pitches a longform profile, complete with photo shoots. For another, it’s not hard to imagine someone like Wiles believing they could outsmart the reporter and control the narrative. But when you give 11 interviews worth of access, you relinquish control. Wiles either got too comfortable or too cocky.

Regardless, the damage is done. Her revelations are out there for everyone to read — and, thanks to recordings, hear.

But just what will the damage be? Are Wiles’ admissions merely salacious or could they hurt Trump and Republicans as we approach a midterm election year?

There’s good reason to believe it will be the latter. Here are the most damning parts of her interview:

Retribution: One of the most immediate effects of Wiles’ interview could be her admission that Trump is pursuing political opponents for retribution. It’s an argument his targets, including New York Attorney General Letitia James and former FBI head James Comey, are making right now to judges who will decide whether those cases have any merit. Expect the comments to end up cited in current and future court filings.

Regime change: Wiles contradicts Pentagon and White House messaging on Trump’s lethal boat strikes, which Defense Secretary Pete Hegseth and Trump have justified as a war on drugs. Wiles admits Trump “wants to keep blowing boats up until [Venezuelan President Nicolas] Maduro cries uncle.” Regime change, in addition to being unconstitutional, isn’t what the America First MAGA crowd voted for, and they’ll likely let him know that. Additionally, that admission could end up being instrumental if someone like Hegseth is ever tried for war crimes.

Tariffs: Wiles says what everyone but Trump seems to know, which is that not everyone agrees with his trade war. Of the rollout, she says “So much thinking out loud is what I would call it.” And, “There was a huge disagreement over whether [tariffs were] a good idea.” As voters gear up for midterms and blame tariffs for rising prices and unemployment, this admission could haunt Trump and Republicans.

Epstein: Wiles absolutely demolishes Attorney General Pam Bondi on her handling of the Jeffrey Epstein files, and how it angered some in the MAGA fold, like Joe Rogan fans. “I think she completely whiffed on appreciating that that was the very targeted group that cared about this,” she says. “First she gave them binders full of nothingness. And then she said that the witness list, or the client list, was on her desk. There is no client list, and it sure as hell wasn’t on her desk.” Discrediting the AG casts a pall on the entire administration, as well as its attempts at burying the investigation.

At a time when Trump’s world is caving in on him, these kinds of free-wheeling, inner-sanctum revelations, and from one of his most trusted and respected advisers, could be disastrous for Trump, disastrous for some of his cabinet members, disastrous for Republicans looking to hold onto their majority.

For a woman known for creating order out of chaos, she just poured gasoline on a fire.

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(S.E. Cupp is the host of "S.E. Cupp Unfiltered" on CNN.)

©2025 S.E. Cupp. Distributed by Tribune Content Agency, LLC.