It seems like just about everyone has a story about the first time they met Donald Trump. The actor Woody Harrelson has recalled his “brutal dinner” at Trump Tower, in 2002, during which the future President dominated the conversation. (“It got so bad I had to go outside and burn one before returning to the monologue monopoly,” Harrelson said.) Richard Branson, the billionaire founder of Virgin Group, recounted a similarly terrible meal, which took place in the nineteen-nineties, shortly after one of Trump’s companies had filed for bankruptcy. “I thought we would have an interesting conversation about a whole range of issues,” Branson said. But, instead, Trump spent the whole time complaining about the people who had refused to help him with his business woes, “and how his life’s mission was going to be to destroy these people.” Meanwhile, Daniel Radcliffe, of the “Harry Potter” movies, has described an encounter that’s just plain odd. Radcliffe was a tween, and he was about to go on the “Today” show, when he ran into Trump. He told Trump he was nervous and that he didn’t know what to talk about on the show. “ ‘You just tell them you met Mr. Trump,’ ” he remembers Trump advising. Radcliffe added, “To this day, I can’t even relate to that level of confidence.”
Unlike Hillary Clinton, who, according to People magazine, sat front row at Trump and Melania’s wedding at Mar-a-Lago, in 2005, a decade before she would spar with Trump on the debate stage, Vice-President Kamala Harris doesn’t have much of a history with her opponent. This was perhaps the biggest revelation of Harris and Walz’s recent CNN interview: “People might be surprised to hear that you have never interacted with him, met him face to face,” Dana Bash said to Harris, of Trump. (“That’s gonna change soon,” Bash added.) Though it’s hard to pinpoint when Trump first met Joe Biden, we know for sure that they overlapped at Trump’s Inauguration, in 2017. Biden, then the outgoing Vice-President, stood on the stage as Trump took his oath of office, and, afterward, they shook hands—less than four years before they would debate.
Why didn’t Harris and Trump meet at Biden’s Inauguration, then, in 2021? Because Trump didn’t go. Still protesting the results of the election, he skipped the ceremony, becoming the first sitting President in a hundred and fifty years to do this. And so Harris and Trump will meet for the first time tonight, in front of us, as if contestants in a new reality show called “Hate Is Blind.”
Trump and Harris might not know each other, but they’ve been in each other’s orbit for quite some time. According to “Kamala’s Way,” an unauthorized biography published in 2021, she once flew, along with then California Assembly Speaker (and future San Francisco mayor) Willie Brown, on Trump’s private plane. Trump wasn’t on the plane: he had sent it to Boston to pick up Brown, who was set to meet with Trump in New York. Harris, then a deputy district attorney, was in a relationship with Brown, and she joined him on board, where, according to Brown, there were “paintings you would usually find in a museum.” Brown recently told Politico that Harris did not join the meeting with Trump. But he did say that he and Harris took a photo on the plane.