Trump's Comedy Fail

Jul 27, 2026

Humor can be a great asset for politicians when they use it effectively. But it also can be miserable when they don’t know how to do it. And that’s what we saw Friday night at the White House Correspondence Dinner with Donald Trump, who is a total stranger to effective humor. Previous presidents have used that occasion to poke fun at themselves or with real humor go after their opponents.

JFK in nineteen sixty two made fun of reporters’ expense accounts. I assure you, that’s a very, very sensitive subject. he also said that he was now convinced that there was a groundswell of support for Barry Goldwater in the 1964 Republican presidential nomination. He said that after he spent a weekend in Palm Beach, Florida.

Ronald Reagan in nineteen eighty six or eighty seven, I believe it was talked about Mario Cuomo from New York, who was widely considered likely to run for president in nineteen eighty eight, seeking a Democratic nomination. And Reagan said, I’ve got good and bad news. He said, the good news is, Governor, there’s a real surge of support for an Italian nominee. But it’s for Lee Iacoca.

Clinton, Obama, and both Bush presidents used good humor at that dinner and people came away, you know, generally feeling good, despite what I think is a dinner that’s over that no longer serves a purpose.

But Trump is a man who is incapable of real humor and he’s incapable of self-deprecation because he’s too insecure. And instead, on Friday night, what he did, he engaged in mean spirited insults. He went after Caitlin Collins, the star CNN journalist who has a temerity to be a good and a tough reporter, and he made fun of fat people he didn’t like. That was ironic coming from the most obese president since William Taft in nineteen twelve. I think this dinner has outlived its useful usefulness. It certainly outlived its usefulness with Donald Trump there.