Robert Smigel, better known for his puppeted alter-ego Triumph the Insult Comic Dog, came face-to-face with nearly the entirety of Trump’s presidential Cabinet on the White House Correspondents’ Association dinner red carpet.
“Honestly, we had no expectation of having that much access to that many people,” Smigel, 66, admitted to Obsessed: The Podcast host Matt Wilstein. “First of all, I didn’t know that practically the entire chain of command was going to be at this thing—and maybe it shouldn’t have."

On behalf of The Daily Show, the SNL alum lashed out at numerous prominent MAGA figures—including RFK Jr., Pete Hegseth, Karoline Leavitt, and Marco Rubio—with his trademarked insult comedy.
“I’m down on my luck, Marco. Please, just one question. Just tell me which country you’re attacking next. I’m trying to win some money on Polymarket. I’m trying to win some money on Polymarket, man! Just give me a wink if it’s Kazakhstan,” Triumph asked the Secretary of State.
“It’s illegal for dogs to gamble,” Rubio, 54, retorted.
Smigel said he got a newfound “respect” for Rubio as a result. “You can only look bad avoiding the puppet or just looking afraid of the puppet,” he added.
“I was kind of half-surprised and half-not that everybody who wanted to speak to me was conservative,” Smigel said, noting that “actual serious journalists” like Wolf Blitzer wanted nothing to do with his comedy.
“I’m like ‘Jesus, what are these people afraid of?’ And they knew I was with The Daily Show for God’s sake," he continued, lamenting CNN host Brian Stelter’s refusal to take part in the bit.

One celebrity who did not veil their distaste for Triumph was actress Cheryl Hines, the wife of RFK Jr.
“Cheryl, what’s special about this night, other than it’s the only celebrity party you’re invited to anymore?” Triumph asked the Curb Your Enthusiasm Actress, to which she grimaced and said, “OK.”
“I had mixed feelings about that interaction,” Smigel admitted. “I just–I know how much c--p she’s taken, and I don’t know her personally, and I don’t know what’s going on in her head.“

“I always have a problem when people want to make fun of stuff that’s really personal, like I didn’t want to do jokes about Karoline Leavitt’s husband being old. I just feel like that’s crossing a line to me,” he continued.
“Well, yeah, you keep it to the horrible things that they’re doing for their jobs, I guess,” Wilstein joked.
“That’s your opinion. I don’t know what you’re talking about, Matt,” Smigel quipped back, laughing.
“In my mind, the joke was as much about her being ostracized, whether fairly or unfairly, than anything personal about her,” he concluded.

Unlike some of the administration members that Smigel spoke to on the red carpet, President Trump has not taken kindly to jokes about him. After the WHCA dinner ended when a gunman fired shots, Trump, 79, and the first lady condemned late-night host Jimmy Kimmel over an inflammatory joke he made two days prior.
“It doesn’t seem to bother their supporters,” he said. “Now, if Jimmy Kimmel had gotten taken off the air, I think it would have lit a fire under some people to realize like, ‘OK, now we’re really cutting into free speech,’” he continued.
“But it’s very frustrating. It feels like a lot of this stuff is just—it’s just fodder to keep you looking this way while everything’s happening over there,” Smigel lamented.
New episodes of Smigel’s podcast, Humor Me with Robert Smigel and Friends, air on iHeartRadio each Friday.
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