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During a Saturday night event hosted by Harvard College’s Intellectual Vitality Initiative, comedian Jordan Klepper advised listeners on how to navigate conversations across the political aisle — but pulled no punches in his condemnation of President Donald Trump, saying the American right has “gone to bonkers.”
The discussion, which was moderated by Kirkland House faculty dean David J. Deming, a Harvard Kennedy School professor, kept the audience on their toes. Klepper — a Daily Show co-host who rose to viral fame by conducting man-on-the-street interviews with Trump supporters at rallies — seemed a natural fit for a program designed to teach students how to have difficult conversations.
But, as Deming repeatedly asked Klepper for insights into his conversational techniques, the comedian sometimes ducked Deming’s questions — or redirected them.
Deming began the conversation by asking about a recent segment where Klepper asked Trump supporters whether they supported blanket pardons for Jan. 6 rioters, then showed them photos of the rioters attacking police. Deming then asked if Klepper’s intervention had changed any minds.
“Did I change any minds at a MAGA rally?” Klepper asked. “Spoiler alert, no, I did not change any minds.”
Deming pressed further.
“What is the purpose of having a conversation like that?” he asked. “Is there anything about that that is consistent with intellectual vitality — to talk to somebody when you know you’re not gonna be able to change them?”
“Oh no, there’s no intellectual vitality,” Klepper said. “My purpose is to get health insurance.”
Harvard’s efforts to promote free speech have coincided with a tack away from addressing political debates head-on. The Intellectual Vitality Initiative, which began in 2020, promotes “rigor, charity, and open exploration” without endorsing partisan stances. In May, the University adopted an “institutional voice” policy that cautions against issuing political statements.
After the Trump administration made a short-lived attempt to freeze federal grant funding last week, Harvard President Alan M. Garber ’76 described the moment in an email as “a period of uncertainty for higher education” — but did not directly condemn Trump’s actions nor vow to fight them.
Garber’s message was in line with Harvard’s non-confrontational approach to the new White House, with University leaders taking steps to mitigate risk rather than launching broadsides against Trump.
Klepper, though, did not shy away from denouncing the president.
“I think Donald Trump is the worst president we’ve ever had in the United States,” he said. “He’s a very dangerous man with fascistic tendencies, and I think he’s an idiot.”
Although he said there was “chaos” on both sides of the aisle, Klepper said that the Republican party has “given up reality.”
Klepper argued that many of the rally attendees he interacted with were trapped in a pro-Trump echo chamber fed by the right-wing media like One America News Network, Breitbart, and their Facebook and TikTok feeds.
“They are taken in by this propaganda by the most powerful person on the planet,” he said. “I empathize with them as humans, but I’m frustrated with the way in which they get manipulated.”
When a student in the audience asked whether intellectual vitality was possible at Harvard given its largely liberal student body, Klepper said students should make an effort to avoid ideological bubbles, but that spaces like Harvard “should be exploring progressive thought.”
“I truly believe that is good for our society,” he added. “This is where you should be exploring ways in which to make the country better and not to be an asshole conservative.”
Deming interjected, saying Harvard students could entertain diverging political arguments, even if they held similar personal views.
“We should be having a diverse range of conversations here, almost regardless of the points of view that our student body and our faculty have,” Deming said.
Klepper recommended approaching difficult conversations “from the standpoint of uncertainty” rather than with the intent to change minds.
“All successful conversations that have moved the needle in any direction, start with that first concession,” Klepper said. “You have to concede a little bit to get anywhere.”
But when Deming prompted Klepper to tell the audience about a time he reconsidered his own point of view as the result of a conversation, Klepper said he “never changed his mind.”
“I’m changing my mind about you right now,” Deming responded.
—Staff writer Samuel A. Church can be reached at samuel.church@thecrimson.com. Follow him on X @samuelachurch.
—Staff writer Cam N. Srivastava can be reached at cam.srivastava@thecrimson.com. Follow him on X @camsrivastava.
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