Why Megyn Says the Donald Trump-Bill Maher Dinner Was ‘Courageous’ for Both Sides

Screenshot/Real Time YouTube

Bill Maher is no fan of Donald Trump, which is why most people were shocked when it was revealed the comedian would be attending a dinner at the White House late last month organized by none other than mutual friend Kid Rock.

The Real Time with Bill Maher host made his way to Washington, D.C., on March 31 for the sit down and had remained mum on the details until now. Maher returned to his show on Friday and offered a candid take on his experience with the “gracious and measured” president.

On Monday’s show, Megyn was joined by Walter Kirn and Matt Taibbi, hosts of America This Week, to discuss Maher’s stunning account and why the meeting was “courageous” for both sides.

Maher’s Meeting Notes

Maher’s criticism of Trump predates even his 2016 presidential bid, which is part of what made his trip to D.C. so surprising. As he explained in his now-viral monologue, he brought a printout with dozens of insults Trump has hurled his way over the years with him to the rendezvous, which the president gamely signed.

The two-and-a-half-hour visit included an Oval Office sit down, tour of the White House, and dinner, and the HBO host said he did not turn “MAGA” and “to the president’s credit, there was no pressure to.” Maher did, however, walk away with a much different impression of the commander in chief. 

“I’ve had so many conversations with prominent people who are much less connected, people who don’t look you in the eye; people who don’t really listen because they just want to get to their next thing; people whose response to things you say just doesn’t track,” he explained. “None of that with him. And he mostly steered the conversation to, ‘What do you think about this?’ I know. Your mind is blown. So is mine.”

He said that freed him up to talk in a way he didn’t expect. “I never felt I had to walk on eggshells around him,” Maher added. “And honestly, I voted for [Bill] Clinton and [Barack] Obama, but I would never feel comfortable talking to them the way I was able to talk with Donald Trump.”

Maher remained skeptical albeit clearly moved. “I’m just taking it as a positive that this person exists,” he said. “Because everything I’ve ever not liked about him was, I swear to God, absent at least on this night with this guy.”

He said he and Trump also agreed on a crucial point while they were viewing MAGA merchandise in what Maher dubbed the “blowjob room” (a nod to Bill Clinton-Monica Lewinsky scandal) off the Oval Office.

“My favorite part of the whole night was we were standing in the blowjob room and he said, ‘You know, I’ve heard from a lot of people who really like that we’re having this dinner. Not all, but a lot.’ And I said, ‘Same. A lot of people told me they loved it, but not all,'” Maher noted. “And we agreed, the people who don’t even want us to talk? We don’t like you. Don’t talk as opposed to what? Writing the same editorial for the millionth time and making 25-hour speeches into the wind? Really, that’s what liberals have?”

Ultimately, Maher had a message for his audience. “That’s my report. You can hate me for it, but I’m not a liar,” he concluded. “Trump was gracious and measured, and why he isn’t that in other settings, I don’t know, and I can’t answer, and it’s not my place to answer. I’m just telling you what I saw.”

Ta-Ta TDS?

Megyn said the visit reflected well on both sides. “I like Bill Maher and I like going on his show, but he definitely has been suffering from a case of [Trump Derangement Syndrome]. Once the TDS gets you, it is hard to come out from under it, but I see shoots of grass… I think he is trying to come out from under it, and, to his credit, he went there,” she noted. “And to his credit, President Trump allowed it, welcomed this, and was very gracious to Bill Maher, who has been brutal about Trump for many years.”

Kirn praised Maher for being honest about what he experienced. “That was a huge risk for him… to be that sincere and genuine. He is taking non-stop hell for it… and I kind of admire him for it,” he explained. “You don’t see actual risks taken in the media. They talk about ‘audience capture’ and how everybody ends up a slave to their audience’s prejudices. Well, he took the risk… and that authenticity is touching to me.”

Unlike Joe Scarborough and Mika Brzezinski’s much-maligned trip to Mar-a-Lago in the aftermath of the 2024 election, which Megyn slammed at the time, she sees Maher’s meeting differently. “The Morning Joe trip… irritated me because I just felt it was performative. I really felt like they wanted access to a person in power who they had been so unfair to for years,” she said. “And I don’t feel that way about Bill Maher or his show at all. I think he is an honest broker, and he has Trump supporters on all the time… so I agree that it was a courageous thing… for both [Maher and Trump] to do.”

Megyn wondered if Maher’s tone towards Trump will change at all in the wake of their meeting, and if that would have an alienating effect on his audience. But Kirn wasn’t so sure it would be a problem. “Every Bill Maher show has something that is a little uncomfortable for people, that doesn’t play to their prejudices or their assumptions,” he concluded. “This is the biggest case of that yet, and I think his audience is going to stick with him. And I think he stays just as tough on Trump, but it will be more issues based.”

You can check out Megyn’s full interview with Kirn and Taibbi by tuning in to episode 1,048 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 Triumph (channel 111) weekdays from 12pm to 2pm ET.