In almost every presidency, the West Wing is a bubble where like-minded acolytes engage in groupthink. But in Trump’s West Wing this phenomenon is exponentially magnified. It’s a parallel universe, one in which the 2020 election was stolen, violent insurrectionists are “patriots,” and the prosecution of political enemies—with scant evidence—is a presidential perk. (“Who would blame him?” Wiles said to me of Trump’s campaign to settle scores.) That, to my mind, is why Wiles seemed so stunned by the firestorm that erupted when her words appeared in my 10,000-word Vanity Fair series last December. She had no idea they would land like bombs on planet Earth.
Wiles invested Trump with almost otherworldly powers. He would lead the GOP to victory in the 2026 midterms, she believed, because of his preternatural ability to rally his base. That’s why, on the eve of the midterms, Wiles was all-in on sending Trump almost everywhere all at once, admonishing people to “vote like I’m on the ballot.” The trouble was voters saw all too clearly what she apparently couldn’t see: Trump was deeply unpopular; on his watch, the country was coming apart.
A year ago, when Wiles made her electoral prediction, I challenged her. “I admire your confidence about the midterms,” I said, “but the stakes are huge, right? And history is not encouraging. Incumbents do stuff and there’s a reaction. And usually, as Obama said, you get shellacked.”
Wiles seemed to shrug off that possibility. “Can you ever imagine Donald Trump saying that?” she said. “No, no.”
Wiles was right. Trump could never say such a thing—because he could never accept the fact that his electoral magic had waned. Neither, it seemed, could Wiles. But as his chief of staff and top political strategist, she was paid to know better.
