Donald Trump’s Talent for Turning Wins into Losses


Donald Trump’s week started Sunday afternoon with one of the biggest personal victories of his presidency. His attorney general’s four-page synopsis of the special counsel’s completed report said the intensive investigation “did not establish” that the Trump campaign “conspired or coordinated with the Russian government,” granting actual credence to what long had been a White House battle chant: “No collusion!” The good news continued with the sensational arrest of nemesis Michael Avenatti and a court case win concerning tariffs. Understandably, it was cause for a victory lap—giddy and combative proclamations on Twitter, a celebratory burst of White House hosting, a jaunty, chest-out trip over to Capitol Hill.

Then … he careened off track.

Barely more than a day after triumphantly (and incorrectly) blazoning his “Total EXONERATION,” Trump abruptly seized upon a Justice Department filing to pledge his intention to obliterate Obamacare. Bent on delivering on a campaign promise, Trump couldn’t resist the urge to try to parlay one win into an even larger one, no matter how improbable the odds. He ignored the advice of top staff and important allies, who pointed out that neither he nor his party had anything to offer as a replacement and that this almost certainly would work to the advantage of Democrats.

While this looked to pundits and even fellow Republicans like a baffling, self-defeating stroke, it was consistent, actually, with Trump’s lifelong patterns. As often as he has proven his talent for turning losses into wins, or at least spinning them that way, there are weeks like this that recall his record for doing exactly the opposite—he also turns wins into losses.

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.

In the 1980s, for instance, Trump racked up a succession of career-constructing conquests. He opened the glass-wrapped Grand Hyatt in 1980. He unveiled Trump Tower in 1983. And toward the end of 1987, in the midst of his first sustained chatter about running for president, his myth-making memoir about his deal-making prowess sold so well it gobsmacked even his publisher and its most ardent promoters.

He responded to this phenomenal stretch by turning a new kind of impulsive and acquisitive. He borrowed too much money to buy too much stuff for too-high prices, running up more than $3 billion of debt that would bring him in a matter of just a couple years to the edge of financial ruin. He overpaid for Manhattan’s Plaza Hotel. He overpaid for the Eastern Air Lines Shuttle, which he renamed after himself. He purchased, too, a piece of a struggling gambling company for the right to build his third Atlantic City casino, which summarily became an albatross. He showed off his gaudy yacht. He cheated on his wife. To Paul Goldberger, then the architecture critic for the New York Times, who observed and chronicled Trump’s willful rise, these actions evoked some combination of Narcissus and Icarus. “He was just sort of pushing harder and harder and less and less aware of the risks he was taking,” Goldberger told me. “In one sense, ’88 was kind of a high point, but it was also clear he was flying a little close to the sun.”

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