Stewart Wonders If Trump Thinks America Is 'Too Small For Him'

Alex Christy
June 23rd, 2026 9:48 AM

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The Daily Show host Jon Stewart sat down with New York Times reporters and authors Maggie Haberman and Jonathan Swan on Comedy Central on Monday to discuss their book on the Trump administration and whether Trump views himself as an Alexander the Great-type figure who thinks America is “too small for him.” Earlier, Stewart, a self-styled comedian, did not appear to understand a joke made by Vice President JD Vance about India and Pakistan and used it to imply he was a racist.

During the interview with Haberman and Swan, Stewart recalled, “By the way, in that interview he hands you a list of people from history that he's been told he's more powerful than, and the list is Mao, Stalin, Hi—”

As Haberman interjected to add “Napoleon,” Stewart continued, “Like, he doesn't go with George Washington. He goes with despots and tyrants and is like, "[Bleep], those guys. I'm bigger than them.”

 

 

He then wondered, “Is America too small for him now? Does he view this as, ‘I’m Alexander the Great?’” as Haberman declared that “There’s something to that, actually.”

A bit later, Swan elaborated on the list, “It was interesting because the document itself basically said Donald Trump is the most powerful man who ever existed on the planet because he's in charge of the U.S. military and technology, but also willing to use the power.”

Stewart interjected to vaguely claim, “And he has plans.”

Swan then resumed, “The people they compared him to, as you mentioned, Mao, Stalin, Hitler, there was no moral dimension to what it was expressed in terms of raw power, and he was reading it out to us and he was sitting across the Oval and he's, like, relishing it. He’s like ‘Napoleon. Mao.’ It's very clear what he wants to do is reshape both America, but also the world. He does, I think, want to be a Napoleonic-type of figure.”

If the criteria for being more powerful than Hitler, Stalin, and Mao is simply being the president of the United States, that really does not say anything unique about Trump.

 

 

Earlier in the show, Stewart was discussing the negotiations with Iran when he introduced a clip of Vance by declaring, “These are the kind of negotiations that will require steely-eyed focus on the American side, and I'll bet JD Vance has just the right touch of gravitas and tact.”

In the clip Vance quipped, “I have joked that I have two very, very important people in my life: an Indian and a Pakistani. The Indian is my wife, and the Pakistani is Field Marshal Munir.”

 

 

Stewart responded by trying to imitate Vance, “My wife is Indian, this dude is Pakistani—boom! You know what I always say, people: two browns don't make a white! Right? Hey! Boom! This guy gets it! Look at me, I'm pointing out their ethnicity. Here's another one: A rabbi, my wife, and Field Marshal Munir walk into a bar—”

The joke is that India and Pakistan have been bitter rivals since they both gained independence in 1947. Stewart is not required to find it particularly funny, but he does have to realize that it isn’t meant to be about brown people.

Here is a transcript for the June 22 show:

Comedy Central The Daily Show

6/22/2026

11:06 PM ET

JON STEWART: These are the kind of negotiations that will require steely-eyed focus on the American side, and I'll bet JD Vance has just the right touch of gravitas and tact.

JD VANCE: I have joked that I have two very, very important people in my life: an Indian and a Pakistani. The Indian is my wife, and the Pakistani is Field Marshal Munir.

STEWART: My wife is Indian, this dude is Pakistani—boom! You know what I always say, people: two browns don't make a white! Right? Hey! Boom! This guy gets it! Look at me, I'm pointing out their ethnicity. Here's another one: A rabbi, my wife, and Field Marshal Munir walk into a bar—

…

11:37 PM ET

STEWART: By the way, in that interview he hands you a list of people from history that he's been told he's more powerful than, and the list is Mao, Stalin, Hi—

MAGGIE HABERMAN: Napoleon.

STEWART: — like, he doesn't go with George Washington. He goes with despots and tyrants and is like, “[bleep] those guys. I’m bigger than them.”

HABERMAN: Top ten. Top ten is what he said to us.

STEWART: The top ten? 

HABERMAN: The top ten, yeah.

STEWART: Is America too small for him now? Does he view this as, “I’m Alexander the Great?”

HABERMAN: There’s something to that, actually.

…

JONATHAN SWAN: It was interesting because the document itself basically said Donald Trump is the most powerful man who ever existed on the planet—

HABERMAN: Yes.

SWAN: —because he's in charge of the U.S. military—

STEWART: Right.

SWAN: —and technology, but also willing to use the power.

STEWART: And he has plans.

SWAN: The people they compared him to, as you mentioned, Mao, Stalin, Hitler, there was no moral dimension to what it was expressed in terms of raw power, and he was reading it out to us and he was sitting across the Oval and he's, like, relishing it. He’s like “Napoleon. Mao.”

HABERMAN: He was delighted.

SWAN: It's very clear what he wants to do is reshape both America, but also the world. He does, I think, want to be a Napoleonic type of figure.

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