Intro

A few weeks ago, we had Sarah Longwell and David French, two prominent conservatives, on Honestly to explain why they’re supporting Vice President Kamala Harris this presidential election. 

There are a lot of people like them—conservatives who are so staunchly never Trump that they are supporting the Democratic candidate. What’s less common—or, at least, less talked about—are the Democrats who are voting for Donald Trump. Maybe there are fewer Democrats crossing the aisle to vote for Trump in 2024, but I’d guess that there are more who are just not willing to speak up because of the stigma. 

Today, we are talking with three people, all of whom have spent their lives identifying as liberal or progressive and are voting for Trump this year—and are loud and proud about it.

Shaun Maguire is a partner at the VC fund Sequoia Capital and has previously started five companies himself. In 2016, he said he was terrified of Trump winning and actively supported Hillary Clinton. But this year, Shaun gave Trump $300,000, saying he believes that “the Biden administration has had some of the worst foreign policy in decades.” 

Maud Maron is a lifelong progressive. She’s dedicated her career to those causes. She was a Planned Parenthood escort and worked for Kathleen Cleaver, the former Black Panther and professor, who called Maud her “excellent research assistant.” She worked for many years as a public defender at The Legal Aid Society until she was canceled by the organization for “wrong think.” Maud ran for NYC’s City Council in 2021 and then for Congress in 2022 as a moderate Democrat. She says she’s no longer a Democrat and will vote Republican for the first time in a presidential election because of, among other things, the Democratic Party’s fixation on race over merit.

Shabbos Kestenbaum is a recent graduate of Harvard, who’s currently suing his alma mater for its failure to combat antisemitism. He says he disagrees with former president Trump on most issues, but on the most important ones, he’s in lockstep with him. Shabbos supported Bernie Sanders and Jamaal Bowman in the past, but has moved right because he has seen firsthand how the excesses on the left have impacted college campuses—and particularly Jewish students—for the worst. 

There are a lot of people who are deeply dissatisfied with the options in this year’s presidential race, and are planning to write in someone on that line of their ballot. Shaun, Maud, and Shabbos are not doing that. They’ve gone the full 180 and are supporting the candidate they once hated. Why?

On today’s episode, how these three former Democrats got so disaffected with their party, how they grapple with the antisemitism on the right, how they contend with Trump’s questionable character, how they square Trump and J.D. Vance’s comments on Ukraine with their hawkish foreign policy views, and much, much more.

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