Jimmy Kimmel has made 3,584 jokes about Donald Trump.
On Monday, he couldn't get a socialist mayor to say one bad word about Donald Trump.
And Jimmy Kimmel got humiliated on live TV when he asked Zohran Mamdani to trash Donald Trump.
The Moment Kimmel Lost the Room
Kimmel pushed hard.
He called the Trump-Mamdani relationship "unexpected."
He asked Mamdani how he charmed the president.
He begged the mayor to send Trump a selfie of the two of them together – live, on air – apparently hoping to embarrass someone.
Mamdani's response?
"Sorry, brother," he said.
That was it.
The socialist mayor who ran on taxing billionaires, freezing rents, and making buses free – the guy Bernie Sanders and AOC cheered at his inauguration – just sat there on ABC's biggest late-night stage and refused to throw red meat at a host who has made his entire career torching Donald Trump.
Kimmel couldn't hide his frustration.
"Wow. You really have broken through with him," Kimmel said after Mamdani described their working relationship.
He then floated whether Mamdani should just move to Washington and "hang out at the Oval Office all day."
Mamdani laughed it off.
"I love you, but I love housing more," he said.
What Mamdani Actually Said About Trump
Instead of taking Kimmel's bait, Mamdani explained the relationship on his own terms.
He told Kimmel that he and Trump have "many disagreements" but share a love for New York City.
He said their conversations have focused on Sunnyside Yard – a massive Queens housing project that would build 12,000 homes and create 30,000 jobs.
"In that moment, I'm just thinking about 12,000 homes," Mamdani said.
https://twitter.com/ReillyBelle57/status/2104806142644007025?s=20
That's not the answer Kimmel wanted.
That's not the answer the left-wing base that elected Mamdani wanted either.
But it's what came out of his mouth anyway – because Mamdani has figured something out that most Democrats haven't.
Getting results for New York City requires not burning down his only phone line to the White House.
The Bigger Picture Kimmel Can't See
Trump called Mamdani a "communist" during the campaign.
He backed Andrew Cuomo against him.
Then Mamdani won – and instead of launching a war, Trump invited him to the Oval Office.
They exchanged phone numbers.
They started texting.
Trump told Mamdani he thought he could "surprise some conservative people" and said, "The better he does, the happier I am."
In February, Trump called him "the new communist mayor" in his State of the Union – then immediately added, "I think he's a nice guy, actually. I speak to him a lot."
That's Trump's version of a compliment.
When world leaders were waiting for him at the UN last week, Trump skipped the line to spend an hour at Gracie Mansion with Mamdani first.
Kimmel wanted Mamdani to blow all of that up for a laugh on late-night television.
The mayor of New York City said no.
Think about what that means.
The most left-wing mayor in New York City history – a guy who got sworn in on a Quran with Bernie Sanders in the front row, who promised to freeze rents and make buses free and tax the rich into the ground – went on the most reliably anti-Trump show on television and spent the whole interview explaining why he needs Donald Trump.
Not why he's fighting Trump.
Not why he's resisting Trump.
But why he needs Trump.
That's what Trump's second term looks like from the outside.
Even the socialists are texting him.
Kimmel can't get that through his head because he's still living in 2020, still running the same bit, still assuming everyone left of center is lined up behind him to perform outrage on cue.
He built his whole career on the idea that hating Trump was a team sport.
Mamdani just told him – live, on his own show, to his face – that he's not playing.
Trump had a room full of world leaders waiting for him at the UN and chose to spend an hour with a democratic socialist first.
That's not a courtesy call.
That's Trump being so dominant that his opponents have to come to him.
Kimmel's still trying to get a selfie.
Sources:
- Hanna Panreck, "Mamdani deflects Kimmel's anti-Trump bait when pressed repeatedly on relationship with president," Fox News, September 29, 2026.
- "Jimmy Kimmel's show overwhelmingly biased against conservatives, study finds," Fox News, 2026.
- Ashley J. DiMella, "Trump meets with NYC Mayor Mamdani at Gracie Mansion ahead of UN speech," Fox News, September 21, 2026.