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Maher shreds Sean Penn for meeting with Castro, Chavez after actor criticizes HBO host’s Trump meeting
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Maher shreds Sean Penn for meeting with Castro, Chavez after actor criticizes HBO host’s Trump meeting

Jimmie Dempsey
Last updated: June 16, 2025 8:28 pm
Jimmie Dempsey Published June 16, 2025
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HBO host Bill Maher accused actor Sean Penn of being a hypocrite this week after the actor slammed the comedian’s meeting with President Donald Trump.

During the latest episode of Maher’s “Club Random” podcast, the comedian and political commentator called out Penn’s meetings with world dictators when the actor pointed out that he wouldn’t have gone to dinner with Trump like Maher had.

“Really, you meet with f—ing Castro and Hugo Chavez, but not the President of the United States?” Maher asked. 

The disagreement came while the two discussed Maher’s meeting with the president at the White House in April. Maher has maintained that the meeting with Trump was “gracious and measured” and suggested the president was a different man in private than he appears on camera.

BILL MAHER DECLARES HIMSELF A ‘HERO’ FOR CONFRONTING TRUMP AT WHITE HOUSE MEETING

Penn met with late Venezuelan president Hugo Chavez in Caracas in 2007. According to Chavez at the time, he and the actor discussed “why the (U.S.) empire attacks Chavez so much.”

The actor also met with late Cuban communist dictator Fidel Castro years prior, as well as Raul Castro in 2008.

Maher began by asking Penn whether he believed having dinner with Trump was the right move. The actor said he could see the reasons why Maher would go to dinner with Trump, but admitted he wished the dinner was perceived as “less successful” for the president than it was, or that Maher had less praise for Trump’s demeanor during their evening together.

Maher disputed that point, stating, “Well, it was less successful because I never stopped saying all the things I’ve always said about him. It would have been successful if he had somehow seduced me into supporting him. So it wasn’t successful.”

CARVILLE RIPS ‘SUPREMELY NAIVE’ BILL MAHER FOR MEETING TRUMP AND PRAISING HIS HOSPITALITY

President Donald Trump and comedian Bill Maher met at the White House.

“The only reason I would not accept an invitation is because I see, I see no – it’s a long flight,” Penn said, struggling to give his answer.

Maher cut him off mid-thought, bringing up his meetings with the Latin American dictators. 

Penn defended himself, saying there were good things that came out of those meetings.

“Yeah, I saw good results come out of some of those things in terms of the agendas that I had… I just personally wouldn’t trust anything that was said in the room, including the personality,” he added, appearing to suggest taking Trump at face value was beyond the pale.

CLICK HERE FOR THE LATEST MEDIA AND CULTURE NEWS

Maher shot back, “It’s not a matter of trusting it. It’s a matter of seeing it, a matter of experiencing it, a matter of knowing it. It’s like saying, ‘I don’t want this medical test because, you know, I don’t want to know.’ I want to know.”

 

“Fair enough,” Penn replied.

Read the full article here

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