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The central problem was that the president was neither inclined to make fun of himself, nor particularly funny himself—at least not, in Conway’s description, “in that kind of humorous way.” George W. Bush had famously resisted the Correspondents’ Dinner and suffered greatly at it, but he had prepped extensively, and every year he pulled out an acceptable performance. But neither woman, confiding their concerns around the small table in Conway’s office to a journalist they regarded as sympathetic, thought Trump had a realistic chance of making the dinner anything like a success. “He doesn’t appreciate cruel humor,” said Conway. “His style is more old-fashioned,” said Hicks. Both women, clearly seeing the Correspondents’ Dinner as an intractable problem, kept characterizing the event as “unfair,” which, more generally, is how they characterized the media’s view of Trump. “He’s unfairly portrayed.” “They don’t give him the benefit of the doubt.” “He’s just not treated the way other presidents have been treated.” The burden here for Conway and Hicks was their understanding that the president did not see the media’s lack of regard for him as part of a political divide on which he stood on a particular side. Instead, he perceived it as a deep personal attack on him: for entirely unfair reasons, ad hominem reasons, the media just did not like him. Ridiculed him. Cruelly. Why? The journalist, trying to offer some comfort, told the two women there was a rumor going around that Graydon Carter—the editor of Vanity Fair and host of one of the most important parties of the Correspondents’ Dinner weekend, and, for decades, one of Trump’s key tormentors in the media—was shortly going to be pushed out of the magazine. “Really?” said Hicks, jumping up. “Oh my God, can I tell him? Would that be okay? He’ll want to know this.” She headed quickly downstairs to the Oval Office. 7 OK Ok Curiously, Conway and Hicks each portrayed a side of the president’s alter ego media problem. Conway was the bitter antagonist, the mud-in-your-eye messenger who reliably sent the media into paroxysms of outrage against the president. Hicks was the confidante ever trying to get the president a break and some good ink in the only media he really cared about—the media that most hated him. But as different as they were in their media functions and temperament, both women had achieved remarkable influence in the administration by serving as the key lieutenants responsible for addressing the president’s most pressing concern, his media reputation. While Trump was in most ways a conventional misogynist, in the workplace he was much closer to women than to men. The former he confided in, the latter he held at arm’s HOUSE_OVERSIGHT_020033