The long-standing friendship between Larry David and attorney Alan Dershowitz collapsed over Dershowitz's decision to represent Trump during his first impeachment proceedings in 2020. After years of being close social acquaintances—with Dershowitz frequently visiting David's home—the two men had a heated public confrontation on Martha's Vineyard in 2021 where David directly told Dershowitz he was "disgusting." In recent interviews, David characterized Dershowitz's role in Trump's legal defence as a morally compromising choice, saying he believes his former friend "made a deal with the devil."

When speaking with journalists, David acknowledged that he should have contacted Dershowitz following the death of Dershowitz's son last year, and expressed some sympathy for how ostracized Dershowitz has become. However, David ultimately maintained that Dershowitz brought the situation upon himself through his professional decisions. Dershowitz has publicly stated that David refuses to speak to him and becomes hostile when they encounter one another, recounting their initial Martha's Vineyard interaction where David rejected his attempt at civil conversation.