When Trump is riding highest, he is simultaneously at his most manic and self-destructive. He overreaches and oversells. He doubles down. In the arc of Trump’s life, from his fevered buying spree in 1988 in the wake of the fame-spiking sales of The Art of the Deal to his wild couple years in the aftermath of the image-laundering launch of “The Apprentice” to his rowdy and improbable political ascent, the craters of his most marked failures follow closely on his most consequential successes. He is this way, say people who know him well, because of his unshakable self-assurance and nerve but also his insatiable appetite for attention and conflict.
“The discomfort he feels in the moment of peace that follows a victory is so intense that he will do whatever it takes to find new fights,” biographer Michael D’Antonio told me.
For Trump, there is no stopping to savor. “If he gets a win, he wants a bigger victory,” added former Trump casino executive Jack O’Donnell.
And this can come at a cost.
“He starts to believe he is invincible,” said former Trump Organization executive Barbara Res.