Jon Stewart returned to The Daily Show with a surgical takedown of Donald Trump’s increasingly erratic response to Kamala Harris’s rising political profile—blending sharp political commentary with absurdist comedy. What unfolded in Stewart’s recent monologue wasn’t just another night of late-night humor; it was a searing dissection of how a political frontrunner like Trump, who once seemed poised to coast to the Republican nomination, has become unhinged by the shifting tides of the 2024 election.
From the moment Stewart welcomed viewers—some possibly tuning in after a “life-affirming” (and entirely fictional) conversation between Elon Musk and Donald Trump—he signaled that the evening would be filled with the kind of surreal political theatre only 21st-century America can deliver. He imagined the two tech-obsessed billionaires quoting Maya Angelou to each other, even joking that “the caged bird is singing for Bitcoin.”
But quickly, Stewart pivoted to the central drama of the night: Trump’s emotional unraveling over Vice President Kamala Harris. Citing reports from The Washington Post, Stewart noted how Trump has been “complaining relentlessly” since Joe Biden announced he would not seek reelection, opening the door for Harris to become the presumptive Democratic nominee. For Trump, who spent years shaping a campaign around opposing Biden, the sudden shift feels like a trapdoor beneath his feet. “Now we have to start all over again,” Trump reportedly fumed. To which Stewart mockingly replied, “Jesus! A month ago, he was basically already the [bleep] president!”
Using gymnastics metaphors, Stewart hilariously described Trump as someone who had nailed the dismount and was on his way to collect a medal—only for “Romania” to file an inquiry and snatch it away. It was a metaphor for how Trump perceived victory within his grasp—only to be upended by an unexpected political twist.
That twist, of course, is Kamala Harris. And Trump, as Stewart points out, doesn’t quite know how to handle her. From mangling her name (“Kamabla”) to publicly pondering her racial identity, Trump has been flailing in a way that’s both comedic and disturbing. Stewart cut to a clip of Trump questioning whether Harris was Indian or Black, then mocking him for acting as though Harris had “made a turn into Black” like she’d taken a wrong exit on the highway.
“Boom, she’s in Harlem!” Stewart shouted, impersonating Trump, making it sound as if Harris’s identity was some kind of navigational error rather than a lived reality.
The segment reached a new level of absurdity when Trump accused Harris of using AI to fake her crowds—an accusation rooted not in evidence but in paranoia. “She cheated at the airport,” Trump insisted, suggesting the large crowd shown in a video was digitally manipulated. Stewart, wide-eyed, deadpanned, “Just because there’s photographic evidence doesn’t mean it was real… Have you considered you’re not real?”
This moment was more than just comedy. Stewart subtly exposed how Trump’s narrative is no longer rooted in political reality, but in delusion—a man so used to bending facts to fit his will that he now accuses reality itself of being fake when it contradicts him.
But it wasn’t over.
The biggest laugh of the night came when Trump claimed to have inside information about Harris from none other than former San Francisco Mayor Willie Brown—who famously dated Harris in the 1990s. Trump recalled being in a helicopter with Brown that had to make an emergency landing, during which Brown allegedly confided that Harris was “the worst.” Stewart, astounded, played out the melodrama: “As you were plunging to your imminent death… he turns and says, ‘Before I die, I must tell you, Kamala Harris is the worst.’”
But, as Stewart soon revealed, it wasn’t even Willie Brown in the helicopter.
The man in question turned out to be Nate Holden, a former Los Angeles City Council member. The confusion prompted Stewart to suggest, not without exasperation, “What are the chances Trump is just mixing up his Black people?”
It was a moment that highlighted not just Trump’s scatterbrained storytelling but also the casual racism that often underlies his commentary. Stewart didn’t need to say it outright—the comedy did the heavy lifting. The implication was clear: Trump’s obsession with Harris isn’t about policy. It’s about identity, optics, and fear—fear of a powerful Black woman who’s climbed too high up the ladder for his comfort.
By the end of the segment, Stewart had both the studio audience and viewers at home laughing uncontrollably, but beneath the comedy was something deeper: a commentary on how America’s political discourse has devolved into spectacle. Stewart isn’t just mocking Trump; he’s exposing the hollowness of his campaign and the bizarre world-building that now defines Trumpism.
Throughout the piece, Stewart didn’t spare the audience, either. He reminded them, subtly, that Trump’s rants resonate with millions. The crowd-size obsession, the fake AI accusations, the racial confusion—these aren’t isolated moments. They’re part of a broader strategy rooted in grievance and performance.
In one of his final remarks, Stewart said, “Donald Trump doesn’t need the fake news media to win this thing… because he’s got inside information from someone she used to date.” It was a line dripping with irony, delivered with comedic perfection, but the message underneath was serious: if this is the foundation of Trump’s attacks on Harris, we may be in for a campaign season more surreal than any before.
Ultimately, Jon Stewart’s monologue was a reminder of what satire can do best—hold a funhouse mirror up to politics and expose the grotesque, the absurd, and the dangerous, all while making us laugh. And in an era where misinformation spreads faster than fact, humor might just be the clearest lens through which to see the truth.