Thirty years ago, I had my first job in PR, at a small Midtown Manhattan firm. This was before HR complaints were really a thing, which was lucky for the managing director, because his behavior would have gotten him fired a dozen times over.
He was also one of the most offensive human beings I have ever met, and the fact that I'm still thinking about him three decades later tells you he left a nasty mark in my memories..
He thought he was hilarious. In meetings, he'd riff on the size of his own anatomy, brag about his sex life with his wife in raunchy details, and disparage women in the room, all while chuckling at his own material.
It was grotesque. But everyone reporting to him laughed, because that's what you did back then. And that laughter did exactly what you'd expect: it convinced him he was the funniest man alive.
I thought about that atrocious boss when I watched Donald Trump's hour-plus “bomb after bomb” performance at Friday night's White House Correspondents' Dinner at the Waldorf Astoria. There he was again.
If Trump had been a contestant on Chuck Barris's old game show "The Gong Show," he would have been gonged in the first 30 seconds. That show existed to publicly end bad performances. Trump went on for more than an hour, only because there was no gong to stop him..
The reason Trump thinks he's funny is the same reason my old boss did. He surrounds himself with people who laugh because they feel they have to, not because anything is funny.
At his rallies, 90 minutes of obscenities and insulting tangents get cheered by a crowd that showed up already believing he's a comic genius. On Truth Social, his posts get flooded with laughing emojis from followers who treat everything he types as the epitome of comedy.
Trump has built an entire ecosystem that reflects his own ego and inflated narcissism back at him, and he's never had to sit with the silence that follows a joke that simply isn't funny.
Friday night, he got that silence. The Correspondents' Dinner crowd wasn't a rally audience or a Truth Social feed. And it wasn’t a room full of yes men like Howard Lutnick and Stephen Miller. It was a room of journalists, people who, for the most part, cover Trump rather than worship him, and who don't laugh on command. And don’t find him funny in the least.
And it showed. As CNN put it, Trump's jokes mostly fell flat, and by the network's own account, "even he could tell, in real time, that many of his jokes were bombing."
The clearest example was when he tried to tell a joke about aging lawmakers. Trump told the room about a senator who got a text from his wife asking him to "come up the stairs and make love to me,” to which the senator supposedly replied, "I can't do both."
No laughs. No laughing emojis. No praise. Just total silence. Trump tried to explain the joke — that’s when you know you’ve told a dud — then explained it again, then gave up and told the crowd, "That was actually the only thing I thought was good in this whole, frickin' stupid speech they wrote."
An 80-year-old man, mocking other aging men for being past their prime, using a joke ultimately about his own stamina and assumed lack of libido, and nobody in the room found it funny but him.
Then there was Kaitlan Collins. About 10 minutes into the speech, Trump used her CNN award to needle her, again, for supposedly never smiling. "You're at CNN fake news. You should be a happy person. So smile, Kaitlan! Just smile,’ before bizarrely and incomprehensibly comparing her to trans activist Dylan Mulvaney. Watching that elicited a loud, “what the ...?” from me.
It’s always been his way of telling a woman her job is to perform pleasantness for him, as misogynistically as possible. What's almost too ironic to invent is that he delivered that riff to a room of reporters who sat there largely stone-faced themselves.
Trump complained about a woman not smiling enough, to a crowd that wasn't smiling at him — at all.
So, Friday night was revelatory in so many ways — well, let’s say redundantly revelatory because we all know Trump stinks at being funny, except when he’s not trying to be funny.
Take Trump out of the sycophantic loop that he's built for himself, the rally crowds, the Truth Social replies, the aides who write his material and the aides who laugh at his vulgarity, and what's left is a joke of a man whose jokes flat out stink, just like him.
Trump is someone who's spent his entire life, even before the presidency, basically being laughed at on command. That’s why he seems incapable of recognizing the difference between real laughter and fake laughter.
My old boss had the same blind spot. He never learned it, because nobody with power over him — at least as long as I had to suffer through him — ever let him feel the silence. Trump felt it Friday night, and the only thing that would have interrupted that silence would have been the bang of a gong.