Some who know Mr. Trump believe that much of the electorate has grown tired of his fate-tempting gambits, even as they expect the 2020 race to tighten eventually against former Vice President Joseph R. Biden Jr., the presumptive Democratic nominee who holds a solid lead in most polls.
“This was sexy and exciting in 2015, 2016,” said Sam Nunberg, a former Trump adviser who worked for him early in his first run. “But for people that have known Donald Trump for a long time like me, I was always worried that he wouldn’t wear well. And he’s at that place now, I think, where he’s not wearing well.”
Mr. Trump seems disinclined to trust anyone else’s judgment on this score, a hesitation born of experience. His life is, if nothing else, a testament to the power of irrepressible salesmanship and taking chances — or at least appearing to take chances — that the risk-averse might discourage.
Throughout his business career, Mr. Trump embraced the label of risk-taker while often eliding the reality of who was assuming much of the risk, spinning failures as successes in the popular imagination.
Gwenda Blair, a biographer of the Trump family, recalled the lessons the president learned from Roy Cohn, the notorious lawyer who mentored him. “The school of Roy Cohn was: You can get away with almost anything,” she said, “that there is in fact not very much risk if you come into the world wealthy, insulated and have enormous political and financial clout when you’re in diapers.”
As his stature grew, Ms. Blair said, Mr. Trump aimed to “make himself big enough that he would push the risk off on everyone else, on all the lenders and banks all the way down to the lowest tradesman and subcontractor who didn’t get paid.”
For Mr. Trump, the psychological upsides were clear. “In some kind of mental jujitsu way, he always wins,” she said. “So, personally, risk isn’t an issue.”