Alan Dershowitz may now be persona non grata on Martha’s Vineyard, especially with Larry David, but the two seasonal residents were once close friends on the tony island.
David once joked that he belonged to a third category when it came to Dershowitz: He knew the famed attorney well — and hated his guts.
The joke was affectionate enough to make it into a video David sent to honor Dershowitz at a Harvard Law School event in 2013, when the two men were longtime friends and Vineyard neighbors who regularly crossed paths on the porch of the Chilmark General Store. More than a decade later, that joke looks very different. David is now opening up about the bitter political rupture that ended their friendship, saying Dershowitz “made a deal with the devil” when he became a lawyer for Donald Trump.
The fallout has now taken on an unexpectedly personal dimension. Dershowitz recently said he was hurt that David never contacted him after the 2025 death of his son, Elon. David acknowledged that he regrets not reaching out — but made clear that his sympathy has not changed his feelings about the choices that drove the two longtime friends apart.
In 2013, the relationship looked remarkably different. Dershowitz recounted to The Vineyard Gazette the tongue-in-cheek video David made and offered a glimpse into how close the two men once were.
“I probably do 60 per cent of my yearly writing in the 10 weeks that I’m on the Vineyard. I get up early in the morning and I work pretty much straight through until exactly 11:45 a.m.,” he told The Gazette. “At 11:45, no matter what, I leave my house and I go to the Chilmark porch for lunch with my buddies [Mr. David among them]. And we sit there, we tell the same old jokes and gossip. We never talk about anything too serious, mostly it’s Vineyard news, and that’s what I do about every day.”
But the friendship eventually collided with the politics that had increasingly defined Dershowitz’s public life.
Dershowitz joined Trump’s defense team during the first impeachment trial in 2020. The following summer, the old friendship erupted publicly on the Vineyard, when David confronted him at the Chilmark Store and called him “disgusting,” according to accounts later confirmed by Dershowitz.
Dershowitz subsequently portrayed the confrontation as part of what he described as a broader campaign to ostracize him from Chilmark because of his defense of Trump. In 2022, he told The New Yorker that David had once come to his house for dinner and worked out in his gym, underscoring just how dramatically their relationship had changed.
Dershowitz isn’t just talking about losing a political ally or a Vineyard social circle. He’s talking about losing someone he considered a friend.
He specifically brought up David’s failure to acknowledge his son’s death. David’s response is notable because, amid the feud, he admitted fault: He said Dershowitz was “100 percent right” that he should have reached out and that he regretted not doing so.
But David didn’t walk back the underlying break.
“He only has himself to blame. He made a deal with the devil. Literally.”
They may now be sworn enemies, but they continue to share a small patch of paradise each summer. Dershowitz has been unusually quiet on the island this year, while David recently donated a lunch-with-him auction package at Possible Dreams that sold for $10,000, with Seth Meyers joking about what the winner would endure.
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