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Patton Oswalt Says Bill Maher Made A Huge Mistake Trying ...
mliss1578 · 2026-05-23 · via New York Post

Comedian Patton Oswalt is weighing in on Bill Maher’s attempts to find common ground with President Donald Trump — and he doesn’t think the strategy was ever going to work.

Appearing on Thursday’s episode of The Dean Obeidallah Show, Oswalt discussed Maher’s now widely talked-about White House dinner with Trump, which the HBO host has continued to reference while defending his willingness to engage with people he disagrees with politically.

Host Dean Obeidallah pointed to Maher as an example of someone who attempted to ease tensions with Trump, only for the president to eventually lash out at him anyway.

“It’s also interesting that the people who try to suck up to Trump or try to make some amends at some point, it doesn’t work out,” said Obeidallah. “Look at Bill Maher. I know you know, Bill, you know he goes to have dinner with him.”

“And at first is saying sort of nice things about Trump. And then Trump just turns on him anyway. Like you can’t win with him. I don’t know what people don’t get that lesson.”

Oswalt agreed, arguing that Trump tends to lose respect for people the moment they attempt to appease him.

“Exactly, the reason that Trump is turning on Bill Maher is because Bill tried to, I’m sure with good intentions, tried to placate him and you can’t do that with him,” Oswalt said.

He then contrasted Maher’s approach with late-night figures like Stephen Colbert and Jimmy Kimmel, both of whom have remained outspoken critics of Trump over the years.

“By defying Trump, this is going to sound kind of weird, Colbert and Kimmel, yeah, Trump hates them but he hates them because they don’t love him. He wants them to love him,” Oswalt explained.

“And then the minute they love him, he has zero respect for them because deep down he hates himself.”

Oswalt added that, in his opinion, sticking to your principles is the only effective approach when it comes to Trump.

“You just have to stick with your guns and just go, yeah, this guy sucks. You know, in the long run, it will pay out.”

The comedian also suggested that even people who align themselves with Trump for business reasons usually wind up regretting it.

“And anyone, anyone who does business with Trump, you would just think basic greed would make you want to defy him,” Oswalt said. “Because anyone that does business with him, you get destroyed!”

Maher, meanwhile, has continued defending his decision to meet with Trump despite criticism from some viewers who saw the dinner as an attempt to soften his stance toward the president.

Watch above around the 6:15 mark via SiriusXM’s The Dean Obeidallah Show.