Alan Dershowitz called comedian Larry David a “mean, nasty man” in a recent interview, explaining how their decades-long friendship ended over his legal defense of President Donald Trump. Speaking on the podcast Pod Force One in May 2026, Dershowitz described a relationship that turned bitter after he began representing Trump during the former president’s first impeachment trial in 2020.
Dershowitz detailed the friendship’s arc during his conversation with Miranda Devine of the New York Post, saying David had repeatedly asked him for favors over the years—including help getting his daughter into college and legal representation—before cutting ties once Dershowitz joined Trump’s defense team. “It was a one-sided friend,” Dershowitz said. “He always asked me for things. He never gave me anything.”
The two men, who had socialized for many years on Martha’s Vineyard, had their most public clash in August 2021 at the Chilmark General Store on the island. According to Page Six, David accosted Dershowitz at the store and told him his ties to the Trump administration were “disgusting.” When Dershowitz said “We can still talk, Larry,” David replied, “No. No. We really can’t. I saw you. I saw you with your arm around [former Trump Secretary of State Mike] Pompeo! It’s disgusting!” The exchange escalated, with David telling Dershowitz, “Your whole enclave—it’s disgusting. You’re disgusting!” before walking away.
Dershowitz characterized David as unable to tolerate political disagreement. In his 2026 podcast appearance, he said he could no longer watch David’s show Curb Your Enthusiasm because he realized the curmudgeonly character was not fictional. “He’s a mean, nasty man, and he can’t tolerate contact with people who have a different point of view from him politically,” Dershowitz explained. “That’s not the kind of friend I want to have.”
Dershowitz’s loss of friendships over his Trump ties reflects a broader pattern of political polarization in American relationships. Research from the University of California, Irvine in May 2026 found that friendships are uniquely vulnerable to political breakups, as they are close enough to allow political differences to surface while lacking the formal structures that preserve family bonds. A 2025 study cited by the New York Post found that just 3 to 8 percent of Americans maintain close friendships across party lines, down sharply from previous years.
The lawyer defended his decision to represent Trump, saying he acted on principle and constitutional grounds, not partisan loyalty. He noted that he is a “liberal Democrat” who voted for Joe Biden and has worked with multiple administrations on Middle East peace policy. Dershowitz told Page Six in 2021 that David was guilty of “contemporary McCarthyism” for refusing to associate with lawyers who represented clients he disagreed with politically.
Sources
- Mediaite — Dershowitz’s May 6, 2026 appearance on Pod Force One, where he called David a “mean, nasty man” and explained the friendship’s end
- Page Six — August 18, 2021 account of the Chilmark General Store confrontation, with direct quotes from Dershowitz and the witnessed exchange
- University of California, Irvine — May 5, 2026 research on why friendships are vulnerable to political breakups
- New York Post — August 2, 2025 study on cross-party friendships, citing 3–8 percent of Americans with close friends across political lines
