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 paradox of the Trump campaign is that its biggest asset, Trump, is also at times its most intractable—a weapon that threatens, at any moment, to blow up in its face. He’s a constant critic of his own operation. “Trump trusts absolutely nobody,” a former top West Wing official told me. That includes Stepien and DeStefano. In recent months, Trump has complained to aides that he’s not being well served by the White House political operation, according to multiple Republicans who’ve spoken with Trump. Trump has told people he questions DeStefano’s loyalty after DeStefano developed a close relationship with the president’s long-suffering chief of staff and nemesis, John Kelly. “Trump openly questions Johnny,” a former official told me. “He asks people, ‘Is he to be trusted?’” A source said Trump has also complained that Stepien is too cautious because Stepien was among advisers who told Trump not to take sides in Republican primary elections.
Presidential approval ratings have shown Trump to be the least popular president in the history of modern opinion polling as of the start of his second year in office. Early polls have shown Trump trailing by a margin of 10–18 percent against several hypothetical Democratic candidates, including Bernie Sanders, Joe Biden, Cory Booker, Elizabeth Warren, and Kirsten Gillibrand. In 2018, the presidential reelection effort and the Congressional midterms both drew presidential campaign attention.