Brand is the be-all-end-all of Donald Trump. And the core of Trump’s brand is that squinty, jut-jowled, unreflective scowl, the Dirty Harry stare he insists on plastering everywhere — book covers, posters, his website—because it advertises his most marketable selling point: toughness.

But the people around the next president of the United States know he’s a lot more insecure than his blustery façade would suggest. And he had a moment of serious apprehension as he toed the diving board before his big leap into the presidential pool on June 16, 2015.

Trump was an uncharacteristic jumble of nerves that whole month, several friends and advisers told me, and he repeatedly asked if he really should go ahead with it. On calls from a summertime vacation in Scotland to buddies back in New York, he would often answer his own question with a reference to his 11th-hour decision to skip the 2012 presidential race: “If I pull out again, nobody is ever going to believe me again.”