Trump’s own data guys have a slightly different interpretation. “The best way to win in 2020 is to win in 2018,” said Bill Stepien, with a straight face. It was a swampy Washington Friday in mid-June, and I was sitting with Stepien, the White House political director, in his office turned war room on the first floor of the Executive Office Building. Virtually every inch of wall space was covered with maps of states with races that Republicans have targeted to win to keep control of the Senate.
Some TV executives say the only way for the Trump show to get canceled is for ratings to fall off — forcing the president to fade into obscurity or an awkward fox trot in a “Dancing With the Stars” spray tan. But TV history shows that the most successful series — “American Idol,” “Lost,” “The West Wing” and, yes, “The Apprentice” — don’t see sharp declines in viewership or talk of cancellation until around Season 6.
These days, Mr. Fleiss does what American TV viewers are doing in record numbers — he sits glued to cable news, watching a panel of experts discuss the latest developments in the sprawling, intricate, unpredictable 24/7 show that is Donald Trump’s presidency. “This is the future of the world and the safety of mankind and the health of the planet,” Mr. Fleiss told me. He paused. “I should’ve thought of that one.”
The possibility that Trump won’t run in 2020 has motivated Republicans serving in his administration to position themselves in ways that would be unthinkable in a normal White House. U.N. ambassador Nikki Haley, who is widely considered to have presidential aspirations, has staked out the Establishment lane. She’s courted Wall Street donors at private dinners in Manhattan and has socialized with former Paul Ryan adviser Dan Senor and his wife, Campbell Brown. Haley rarely mentions Trump in her public speeches. According to a Republican close to Trump, Trump has been annoyed with this omission. “He’s gotten feedback she never mentions his name at events,” the Republican close to the White House said. “Nikki is ambitious. She’s going to run. It’s just a question of when,” a former West Wing official said. “Her staff is very careful when they speak to other people. They always say 2024; one of Haley’s people told me 2024 is code for 2020.” (A Haley spokesperson said, “Ambassador Haley is not running for any office in 2020.”)
Trump's predecessors merged their campaign committees into their party's committee following their election victories. Following his 2016 election victory, Trump eschewed this presidential tradition and retained a separate campaign committee. Trump's campaign committee continued raising funds. In December 2016, the campaign raised $11 million. These moves indicated that Trump was already eying a 2020 run.