President Donald Trump appeared at the rescheduled White House Correspondents’ Association (WHCA) dinner Friday night after previously skipping the event throughout both of his terms.
The gathering at the Waldorf Astoria hotel in Washington, D.C., served as a scaled-down replacement for the April dinner that was postponed after an armed man charged toward the venue inside the Washington Hilton and opened fire before being taken into custody.
The president spent roughly an hour at the lectern roasting the media and members of his own administration, while repeatedly acknowledging the muted response from a ballroom dominated by reporters and media executives deeply hostile to him.
The Joke
One of the jokes that failed to land involved CNN host Kaitlan Collins and controversial ‘trans’ influencer Dylan Mulvaney, and it also revealed an inconvenient truth for the leftists in attendance.
“[Trump] is getting a lot of crap for the jokes he told about Kaitlan Collins, who is never nice to the president. She is always nasty… Her questions always have the most negative bent you could possibly go into the questioning with,” Megyn noted on Monday’s Megyn Kelly Show. “So, the president did what all presidents do. He got up there and he gave her a little jazz… But the press didn’t like the way he did it.”
At the dinner, Collins received the WHCA award for Excellence in Presidential News Coverage Under Deadline Pressure, which President Trump quipped was “fake” before revisiting his past comments about her serious countenance.
“She’s a young, attractive woman. She never smiles. I said, Kaitlan, do you ever smile? Smile. You have a nice position. You’re at CNN fake news. You should be a happy person. So smile, Kaitlan. Just smile,” Trump said. “I thought Kaitlan had really made it big with a major new sponsorship, but then I informed her that it wasn’t her on the Bud Light can. It was Dylan Mulvaney.”
That was a reference to Bud Light’s ill-fated 2023 partnership with Mulvaney for a March Madness promotion that ended in a prolonged boycott of the beer maker and a more than $27 billion loss in market cap for Anheuser-Busch.
A Prisoner’s Dilemma
Needless to say, there were no laughs at the line that, in Megyn’s view, put those in attendance in a unique predicament. “It is clever because it puts the left in such a difficult position… They have to say that’s not complimentary, so they have to rip on a trans person, which they definitely don’t want to do,” she noted.

Rather than back down, Trump doubled down. He posted a meme on Truth Social Sunday of Collins’ face superimposed on Mulvany’s social media post from the Bud Light collab in which he was inexplicably dressed like Audrey Hepburn in a black dress and gloves and bouffant ‘do while sitting with beer cans.
The kicker? Collins is smiling in the fake photo.
“She is smiling here, so they are horrified by that too,” Megyn noted. “He has put them in a very difficult position because you basically have to say it is insulting to compare her to Dylan Mulvaney. Why is it insulting? Because Dylan Mulvaney’s a man. They just won’t close that circle, but we all know why they find it insulting.”
You can check out Megyn’s full analysis by tuning in to episode 1,368 on YouTube, Apple Podcasts, or wherever you like to listen. And don’t forget that you can catch The Megyn Kelly Show live on SiriusXM’s The Megyn Kelly Channel (channel 111) weekdays from 12pm to 2pm ET.