‘My Whole Life Is a Bet.’ Inside President Trump’s Gamble on an Untested Re-Election Strategy

‘My whole life is a bet,’ the President of the United States says, resting his forearms on the edge of the Resolute desk in the Oval Office.

It’s a steamy evening in mid-June, and Trump is facing a set of high-stakes tests around the world. Tensions rising with Iran. Tariffs imposed by India. Protesters flooding the streets of Hong Kong. But Trump is confident, ready to joust. He has invited a group of TIME journalists for an interview, blown past the allotted time and settled in for a wide-ranging discussion. Along the way, he orders a Diet Coke with ice with the push of a small red button set into a wooden box on the desk, and directs an aide to fetch a copy of a hand-delivered birthday letter sent from Kim Jong Un.

Politics is rarely out of mind for any man who wills his way into this rarefied sanctum. Especially not one who calls his campaign manager on many days by 7 a.m., and certainly not now, the day before Trump formally kicks off his 2020 re-election bid. So it doesn’t take much prodding for the President, a former casino magnate, to start making book on the sprawling field of Democratic challengers.

A “progressive” will probably win the primary, Trump predicts, running down the competition with evident relish. Joe Biden “is not the same Biden,” he says, adding later, “Where’s the magic?” Kamala Harris, he notes, “has not surged.” Bernie Sanders is “going in the wrong direction.” Elizabeth Warren’s “doing pretty well,” he allows, but Pete Buttigieg “never” had a chance.

Why? “I just don’t feel it,” Trump says. “Politics is all instinct.”

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