A longtime Martha’s Vineyard friendship between comedian Larry David and attorney Alan Dershowitz has turned into one of the island’s most talked-about celebrity feuds, and David has now offered his bluntest explanation yet. After The Atlantic revisited Dershowitz’s claims that he has become socially isolated, David first expressed regret over one deeply personal omission before delivering a far harsher political verdict.
David and Dershowitz were once close summer neighbors who spent time together at Dershowitz’s home, where David reportedly attended dinners and used the gym. But their relationship began collapsing after Dershowitz joined Donald Trump’s legal defense during the president’s first impeachment trial in 2020. Years later, David says Dershowitz “made a deal with the devil” — while Dershowitz continues to argue that he has paid a heavy social price for his legal and political choices.
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Larry David and Alan Dershowitz’s Friendship Fell Apart After Trump’s Impeachment Defense
For years, David and Dershowitz were familiar faces around Martha’s Vineyard. Dershowitz recalled that David would visit his home two or three times each summer for dinner and would sometimes work out in his gym.
That changed dramatically when Dershowitz became part of Trump’s legal team during the first impeachment trial in 2020.
Dershowitz has repeatedly maintained that he is a lifelong Democrat, pointing to his votes for Hillary Clinton in 2016 and Joe Biden in 2020. His argument was that representing Trump was about legal principle and the right of controversial political figures to receive legal representation.
For David, however, the decision appears to have crossed a line.
The feud became impossible to ignore in 2021, when the two encountered each other at the Chilmark General Store. Dershowitz said he was sitting on the porch with a friend when David arrived. He greeted the comedian, but David turned away.
Dershowitz recalled trying to reopen communication.
“We can still talk, Larry.”
David apparently refused. After seeing Dershowitz with former Trump Secretary of State Mike Pompeo, he responded:
“It’s disgusting. Your whole enclave — it’s disgusting. You’re disgusting!”
David then walked away.
Dershowitz later described the encounter as extremely heated, saying David screamed and yelled and became bright red. He even worried that the comedian might suffer a stroke.
Dershowitz has insisted that his interaction with Pompeo was not a political alliance. Pompeo had previously been his student at Harvard Law School, and Dershowitz said his gesture toward him was connected to his admiration for Pompeo’s work concerning Middle East peace. He gave a detailed account of the confrontation in a 2022 interview with The New Yorker.
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But the Chilmark incident became the defining moment of a friendship that had once seemed completely ordinary.
Then came a much more personal wound.
In The Atlantic profile published August 18, 2026, Dershowitz said David still refuses to speak with him except during angry encounters.
“Larry David doesn’t talk to me anymore. He screams and yells at me when he sees me.”
Dershowitz also said he had once enjoyed Curb Your Enthusiasm but could no longer watch the show.
The most painful part, however, involved his son, Elon Dershowitz.
Elon, a film and podcast producer, died from a stroke on August 17, 2025, at 64. He had survived a childhood brain tumor that left him unable to read or see well and remained close to his father, frequently accompanying him on Martha’s Vineyard.
According to Dershowitz, David knew Elon well but never contacted him after the death.
“Even when my son died—and Larry knew him very well—he never sent me a card. Never called me, never did anything to acknowledge it.”
When The Atlantic contacted David, his initial response was almost bewildered.
“I don’t know why he’s still thinking and talking about me.”
David also joked about the confrontation, saying:
“I have lots of confrontations on my show but rarely in life. And then only if I think I can take them in a fight. Hence the Dershowitz dust-up.”
But when asked about Elon, David admitted that Dershowitz was right.
“He’s 100 percent right. I should have reached out, and I certainly regret not doing so. As I said on Curb once, ‘I think of nice things. I just don’t act on them.’”
David said he was “starting to feel a little sorry for him, actually. Certainly because of his son,” and described himself as “softening.” He appeared to leave the door open to some form of reconciliation.
Then, just one day later, the tone shifted.
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David sent The Atlantic another message, this time sharply criticizing Dershowitz’s political and legal choices.
“I’m loath to say anything mean because he’s been so ostracized. But he only has himself to blame. He made a deal with the devil. Literally. And I’d bet the devil hasn’t said a word to him since the impeachment.”
That line became the clearest expression yet of why David believes their friendship broke down. His criticism was aimed not simply at Dershowitz having different political opinions, but at his decision to represent Trump.
Dershowitz, meanwhile, has repeatedly described his treatment on Martha’s Vineyard as social ostracism or “McCarthyism.” He has connected the hostility to his representation of controversial clients including Jeffrey Epstein, O.J. Simpson and Harvey Weinstein, as well as his strong support for Israel.
He has said former friends have shunned him, social circles have excluded him and businesses or individuals have sometimes refused to serve him. In 2025, he said a vendor at a West Tisbury farmers’ market refused to sell him pierogi. He has described the reception in Chilmark as “90 percent negative,” while saying other parts of the island have been more welcoming. During winters in Miami Beach, he says he has experienced a friendlier environment, and he has developed new social connections through a local Chabad.
The political divide has also grown.
In April 2026, Dershowitz announced that he was leaving the Democratic Party after decades of identifying with it, calling Democrats the “most anti-Israel party in US history” and saying he was moving toward the Republican Party. His forthcoming book, Why I Quit the Dems: And So Should You!, subtitled Confessions of a Reluctant Republican, is scheduled for September 2026 and includes a blurb from Trump.
In June 2026, the U.S. Supreme Court declined Dershowitz’s request to revive a $300 million defamation lawsuit against CNN. He had sued over coverage of comments he made while defending Trump, arguing that his remarks had been edited to falsely suggest he “had lost his mind.”
For now, the former friends still spend summers on the same island, but there is no indication that the relationship has recovered. David’s comments reveal an unusually complicated position: he regrets not reaching out after Elon’s death and says he had begun feeling sympathy for Dershowitz, yet he simultaneously believes Dershowitz’s own choices are responsible for the isolation he describes.
That leaves their feud in an awkward place — somewhere between personal regret, political condemnation and a friendship that, at least for now, remains broken.
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Disclaimer
This article is based on contemporaneous reporting and statements attributed to Larry David, Alan Dershowitz and the publications cited below. Statements concerning personal disagreements, political views, social ostracism and other allegations are presented as reported or as statements made by the individuals involved and should not be interpreted as independently established facts beyond the available reporting. The article does not imply that any person’s political affiliation, professional representation or association with another individual establishes wrongdoing.
Sources
- The Atlantic
- The Guardian
- Variety
- Page Six (2021 confrontation)
- Variety (2022 confirmation)
- Times of Israel (party switch)
- AP News (SCOTUS CNN suit)
- MassLive (pierogi incident)
Featured Image Credit:
- Angela George / Wikimedia Commons (CC BY-SA 3.0)
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