In Fire and Fury, Michael Wolff describes the president's complicated relationship with the media.
Years before the campaign, when Trump was famous as a New York real estate mogul, he had sought the limelight. Roger Ailes said that, to Trump, “the media represented power, much more so than politics". Wolff relates:
"The media long ago turned on Donald Trump as a wannabe and lightweight, and wrote him off for that ultimate sin — anyway, the ultimate sin in media terms — of trying to curry favor with the media too much. His fame, such as it was, was actually reverse fame — he was famous for being infamous. It was joke fame."
Furthermore, he was known for his bankruptcies.
"Whereas he [Trump] had before been the symbol of success and mocked for it, now [in the 1990s] he became, in a shift of zeitgeist (and of having to refinance a great deal of debt), a symbol of failure and mocked for it. This was a complicated reversal, not just having to do with Trump, but of how the media was now seeing itself. Donald Trump became a symbol of the media’s own self-loathing: the interest in and promotion of Donald Trump was a morality tale about the media. Its ultimate end was [New York Observer editor Peter] Kaplan’s pronouncement that Trump should not be covered anymore because every story about Donald Trump had become a cliché."
The presidential campaign was different. His former celebrity was not a fulfillment in itself. Journalists now expected him to make factual statements. He was bedeviled by "the media, which, with its conclusion of a misbegotten and bastard presidency, believed it could diminish him and wound him (and wind him up) and rob him of all credibility by relentlessly pointing out how literally wrong he was. The media, adopting a 'shocked, shocked' morality, could not fathom how being factually wrong was not an absolute ending in itself."
He was in a bind:
"Trump craved media approval. But, as Bannon emphasized, he was never going to get the facts right, nor was he ever going to acknowledge that he got them wrong, so therefore he was not going to get that approval. This meant, next best thing, that he had to be aggressively defended against the media’s disapproval. The problem here was that the more vociferous the defense — mostly of assertions that could easily be proved wrong — the more the media redoubled its attacks and censure. What’s more, Trump was receiving the censure of his friends, too."
"The fabulous, incomprehensible irony that the Trump family had, despite the media’s distaste, despite everything the media knows and understands and has said about them, risen to a level not only of ultimate consequence but even of immortality is beyond worst-case nightmare and into cosmic-joke territory." Donald Trump and his son-in-law Jared Kushner had been subject to the same media pressures as New York celebrities, "never quite understanding why they should be the butt of a media joke, and now," together in the White House, "the target of its stunned outrage."
Meanwhile, when his allies were the subject of media criticism, "he blamed them and their inability to get good press."
Trump wanted to be universally praised in the media. He did not understand that, in politics, some outlets would always be positive and some would always be negative.
"The conundrum was that conservative media saw Trump as its creature, while Trump saw himself as a star, a vaunted and valued product of all media, one climbing ever higher. It was a cult of personality, and he was the personality. He was the most famous man in the world. Everybody loved him — or ought to. On Trump’s part this was, arguably, something of a large misunderstanding about the nature of conservative media. He clearly did not understand that what conservative media elevated, liberal media would necessarily take down. Trump, goaded by Bannon, would continue to do the things that would delight conservative media and incur the wrath of liberal media. That was the program. The more your supporters loved you, the more your antagonists hated you. That’s how it was supposed to work. And that’s how it was working. But Trump himself was desperately wounded by his treatment in the mainstream media."
The polarization left Americans with a difficult decision of whom to trust. There were now "two unreliable narrators dominating American public life," as Wolff put it, if you accepted the argument of Mark Hemingway in the Weekly Standard: the President-elect, who "spoke with little information and frequently no factual basis," and the media, which treats everything he does as, "by default, unconstitutional or an abuse of power."
The president's need for positive attention from all directions revealed that he
"quite profoundly seemed unable to distinguish between his political advantage and his personal needs — he thought emotionally, not strategically. The great value of being president, in his view, was that you’re the most famous man in the world, and fame is always venerated and adored by the media. Isn’t it? But, confusingly, Trump was president in large part because of his particular talent, conscious or reflexive, to alienate the media, which then turned him into a figure reviled by the media. This was not a dialectical space that was comfortable for an insecure man."