Fox News had made Donald Trump’s political career, but now it was flailing due to a dichotomy of a conservative father and liberal sons. The sons were winning in a sense, because Bill O’Reilly had been pushed out on April 19 due to sexual harassment allegations. Roger Ailes had already been pushed out earlier and was contractually obligated not to compete with his former company for eighteen months. In secret, he was plotting a comeback with a new conservative network and was interested in recruiting Steve Bannon. The belief among both was that Trump the President was created through right-wing media. With the Murdoch sons taking over, the time was ripe for a new conservative network and Breitbart had tapped into a wellspring within the younger generations. Ailes thought he could get O’Reilly and Sean Hannity on board. Since Steve Bannon’s star was falling in the Trump administration, this could provide a powerful opportunity. Steve Bannon was still trying to make an impact in the Trump White House, but he was interested.
Trump thought he was bigger than conservative media and conservative media, in turn, thought it had created him. What Trump didn’t understand was that there are different kinds of “Media”. If conservative media pumped him up, liberal media wanted to take him down. Trump was regularly hurt by this and nursed every single criticism or slight, even replaying negative press over and over again on his DVR. He never blamed himself. He blamed his subordinates for not getting good press. He wanted everyone in the media to love him and couldn’t fathom the conservative/liberal love/hate dynamic. He just didn’t understand that media regard for him depended on political perspective and instead took everything as a deeply personal attack.
As soon as Trump’s team moved into the White House, everyone worried about the Correspondent’s Dinner. Trump did not like being made fun of and he wasn’t particularly funny. Given his feelings on such direct humor, staff members didn’t really know what to do. The job fell to both Kellyanne Conway and Hope Hicks. In a way they were Trump, externalized. Kellyanne was the attack dog, infuriating the media with her aggressive, non-apologetic retorts, while Hope Hicks was constantly on the lookout of for any positive press.
In a strange sort sort of way they were perfect for their jobs. Trump trusted women more than men. This was largely because he felt that women, by nature, wanted to attach themselves to a man, with Trump being the best man to attach to. He felt women understood him and the most successful women in his orbit did, in a way. They understood he was a man controlled by his needs want impulses. Those that were willing to do it gave him the extra-special handling that he craved.
Conway understood this immediately. She had been brought on by the Mercers, but had identified quickly what made Trump happy. In her interview with him she vowed only to call him as “Mr. Trump”. Her perceive loyalty and submission landed her in the job of cable spokesperson. In Trump’s mind, one of the most important jobs.
Privately, Conway was absolutely exhausted by Trump, gesturing often to illustrate his insanity. In public, however, she was his most ardent TV warrior. Trump loved it. He wanted her to be his press secretary, although it appears there was a push to keep her away from that position. Trump loved her over loyalty, but others in his orbit were repulsed by her take-no-prisoners on-screen tactics. Jared and Ivanka, in particular, here disgusted with her. They worked to sideline her, leaking about her and moving her to second-rate and right-wing media with no real decision-making power of her own.
This seemed to deepen her bond with Trump, however. She blamed the media and the two of them would commiserate about how cruelly they were being treated.
Hicks knew right away that she had to shy away from the media as much as possible. She started out doing some PR work before moving to Ivanka Trump’s fashion business and then transitioning to Donald Trump’s campaign team. Her family viewed it somewhat akin to being taken captive. She was as surprised as anyone where things went from there, but she also dedicated herself to being the perfect Trump support employee, completely tolerant of and subservient to the man himself. Her limits appeared on occasion, however. She had been in an on-and-off relationship with Corey Lewandowski, another Trump campaign employee. When she mused one day about some bad press Lewandowski was receiving, Trump turned to her and said “Why? You’ve already done enough for him. You’re the best piece of tail he’ll ever have.” He seemed to mean this in sort paternal and protective way, but it sent her running from the room.
Nevertheless, she was loyal. The other staffers thought of her as Trump’s real daughter and of Ivanka as Trump’s real wife. She was entrusted with being the vessel through which Trump managed his vessel and image. Her one failing was getting a good write-up for Trump in the New York Times. Because of this, he once affectionately greeted her by saying “You must be the world’s worst PR person.”
Trump wanted the press secretary to be a good-looking woman because that was what came across well on television. There was another view that the position shouldn’t be seen as important as it was. This was Bannon’s view. The press won’t come around on Trump, so why pander to them? It was Priebus who pushed for Sean Spicer to get the position. Spicer himself had doubts. He was worried that after working for Trump he’d never work in town again.
Once he took the job, he was under constant pressure. Trump was constantly giving instruction and insult to Spicer’s work. The stress rattled Spicer to the point of every press conference becoming a TV disaster. For his part, Trump would huddle with Hope Hicks and obsess about media personalities, cable anchors, producers, reporters and agendas. One particular person was Maggie Haberman, a New York Times reporter. She had exceptional access to the President but never wrote the kind of press he wanted. Staffers wondered why Trump kept giving her access and the running theory was that he was trying to return to the glory days of press when Haberman covered Trump at the New York Post. Way back then, the press was all about the glory of Trump. Beyond that, Trump had no kind words for Haberman.
Kushner, Trump and Bannon basically each had their own press operations. Kushner and Bannon both leaked so much that each could identify the other’s leaks. Kushner’s team included Josh Raffel, who came out out of the same PR shop as Hope Hicks. Banner had Alexandra Preate, who had worked for Breitbart and was close to the Mercers. Preate was not officially part of the White House, unlike Raffel. She was solely an agent for Bannon. It also gave Bannon leverage, since he would wield the Breitbart hammer against anything Jared and Ivanka did. This made Trump’s White House the most media-dysfunctional communications team in modern history.
Everyone was desperate to keep Trump away from that dinner. He was convinced he could go in, improvise a bit, and win the crowd. Everyone else expected his head to explode. Bannon felt like going would make it look like Trump was needy for the media. It turned out this was the right angle to take. Trump didn’t want to seem weak, so he didn’t go, which made everyone in the White House feel better.
Rather than go to the dinner, Trump went to give a speech at Harrisburg, Pennsylvania. The point was to show that he wasn’t interested in the pomp and circumstance of Washington and would rather be among “the people”. Although he professed not to care at all about the dinner, when away from the crowd he repeatedly asked for updates on the jokes.