Bill Maher Mocks Trump's 'Macho' Team as 'the Gayest' Administration While Joking About His Shoe Size Fixation
Bill Maher mocks Trump's team as 'the gayest' administration.
March 14 2026, Published 5:35 p.m. ET
Bill Maher delivered a biting roast of President Donald Trump and his inner circle during his latest Real Time monologue, RadarOnline.com can reveal.
The comedian mocked the administration's "macho" image while joking about Pete Hegseth's alleged photo ban and Trump's bizarre habit of guessing other men's shoe sizes.
'Little Nervous in Our War Room'
Maher also poked fun at reported Pentagon restrictions on photos of Pete Hegseth.
Maher kicked off the segment by making clear he wasn’t siding with America's adversaries, even as he criticized what he sees as strange behavior coming from the administration.
"Don't take that the wrong way. I'm on our side. OK, I'm for us winning, right?" Maher told the audience, per Mediaite. "I'm not on that page of Trump did it, so I'm with the Ayatollah now."
But the host quickly added that the optics surrounding the administration have left him puzzled.
"But I got to say, they are looking a little nervous in our war room," Maher continued. "The Pentagon banned photographers this week for the briefings because Pete Hegseth said some of the pictures of him looked unflattering."
Photo Ban Raises Eyebrows
The host mocked Trump's habit of guessing other men's shoe sizes.
Maher used the moment to poke fun at what he described as a contradiction between the administration's tough image and the reported sensitivity around photographs.
"Pete wants you to know two things about our military," he joked. "This is the new alpha male, very masculine, non-woke military. Also, don't get my bad side."
The quip drew laughter from the audience as Maher leaned further into the punchline.
'The Gayest'
Maher joked the entire cabinet has received shoes from the president.
The comedian then delivered the line that quickly became the highlight of the monologue.
"So this is the most macho administration we've ever had," Maher said. "Also the gayest."
Maher quickly clarified that he wasn’t speaking literally, adding with a shrug: "I gotta say. I don't mean litera–, I just, a lot of redecorating. I'm just saying."
Donald Trump's Shoe Size Game
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Marco Rubio even ended up in 'clown shoes,' Maher quipped during the bit.
Maher then turned his attention to another topic he found equally baffling — Trump's reported fascination with guessing other men's shoe sizes.
"Also, Trump has a new thing. I'm not making this up," Maher said. "He's guessing other men's shoe size."
The comedian leaned into the absurdity of the idea as the audience laughed.
"Have you seen, am I making this s--- up? I'm, he has been."
According to Maher, the guesses sometimes come with gifts.
"He looks at other men and guesses their shoe size, and then they send them a pair," he said. "The entire cabinet is wearing shoes he got them."
Maher added that not everyone received the perfect fit.
"Including Marco Rubio, where they didn’t fit, so he's in clown shoes," the host joked.
He wrapped the bit with one last punchline.
"I'm just saying," Maher told the crowd. "It's a little weird for a man to look at other men and go, 'What you got down there, a nine and a half?'"
