Sims introduces the book by describing his initial meetings with Donald Trump. The contact between him and Trump happened out of Sims’ curiosity, more so to understand why he wanted to run for president. Sims notes that, “It was still unclear, at least to me, whether the Trump candidacy was a fad—a chance for voters to vent their frustration with political correctness and the status quo before they got serious with another candidate. Predictions of Trump’s imminent implosion, over one incendiary thing he said or did after another, were an almost daily occurrence.” Despite being aware of Trump’s personality issues, Sims indicates that he was surprised by how a lot of people appeared to be embracing him. Most importantly, Sims says that a pollster had informed him that when Trump announced his desire to run for president, his intention was not to win the elections — but to merely promote his brand.
During the early days of the campaign for the Republican ticket, Sims shares his dismay — not with how Trump’s popularity was rising, but with his “larger-than-life persona”. Trump has a habit of steamrolling his interviewers, and Sims needed to be cautious in his approach to interviewing the president-to-be. Notably, he asserts that, “A poll released the week before showed Trump lapping the rest of his Republican opponents in Alabama. But it wasn’t his polling numbers that made me nervous. It was his entire larger-than-life persona.” It was always difficult for reporters as they sought to engage Trump on critical national issues. Ordinarily, any person seeking to be the President of the United States must be prepared to encounter very tough questions on a wide range of issues facing the country. However, Trump was always quick to dismiss any journalist who sought to question or to scrutinize his suitability to occupy the Office of President of the United States. Sims did not want to fall victim to Trump’s vicious attacks — and thus, he had to find a brilliant approach to engage him.
Sims ventures into unpredictability when he engages Trump on the issue of abortion, saying that he had done his research and discovered that Trump was pro-abortion. Nonetheless, during this interview, Trump indicated that he was pro-life. Sims annals that, “Trump did, indeed, say during that interview that he “hated the concept of abortion”. But Trump had also said he was “very pro-choice”—a fact he now wanted to gloss over as if it never existed. This would, of course, be a recurring habit.” In this statement, it is notable that Trump is emerging as an unstable leader, one who hates to make decisions and statements, and subsequently stand by them — yet doing so only when it is convenient. These are some of the qualities of President Trump that Sims says would, later on, be manifested in his administration.
While Sims found Trump’s rivals in the race for the Republican ticket, such as Marco Rubio and Ted Cruz, to be more appealing on many issues, he, however, was inclined to agree with Trump on the issue of immigration. Sims says that, “Ideologically I was more aligned with Ted Cruz, a rock-ribbed conservative who’d been giving the party establishment fits since getting elected to the Senate a few years before. Stylistically I was drawn to the aspirational tone of Marco Rubio.” He also mentions that while other people may find it awkward, the issue of the border wall — which Trump was presenting to the voters in the campaigns — was a source of attraction. While it was an unpopular position among a significant number of voters, the fact that Trump was able to stand by it gave him some credibility. Despite Trump’s numerous flaws, the author also points out the numerous areas where he performs well.
Towards the closing of the first chapter, Sims discusses the conflict he faced when deciding whether to support Trump or the Democratic nominee, Hillary Clinton. He declared himself as being a liberal Republican, and that he was always willing to support any candidate whom he thought would address his needs as a citizen. To Sims, Clinton was a corrupt fellow who did not deserve to come anywhere near to the Oval Office. So while Sims has reservations about the leadership of Trump, the alternative seemed less desirable — being the deciding factor behind his decision to join his campaign team in an official capacity.