The Free Press
Honestly with Bari Weiss
The Democrats Voting for Trump
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The Democrats Voting for Trump
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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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118

100% Same. I’ve voted Democrat since 2008. I donated and campaigned for Biden, Clinton and Obama. I’m voting for DJT because CA is coming apart at the seams; CoL is astronomical; we are flush with drugs, homelessness, and crime; kids are being screwed up in school with gender ideology and racist ideas; universities are overrun by antisemitism; my job is constantly pushing woke ideology on me like I’m a race/gender studies major at uni; unfettered illegal immigration is a disaster. Enough. I don’t like DJT, but I want the Democrats in their current form to be brought to their knees and repent for the insanity they’ve unleashed. I fear them more than a DJT presidency.

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I've just started listening to this podcast, but already I feel great relief in that I expect to hear legitimate thought processes by people who have truly listened to what each side is saying. The Republicans for Harris episode was a disappointment - pure emotional reaction from 2 people who clearly never actually listened or watched any of the more reasonable formats Trump participates in (any one of the many interviews he's done over the past months with a more friendly interviewer would be a good start). Most people (and I'd suggest virtually all Democrats) only watch sound bites on MSM or one of the highly televised (again, MSM) debates or press conferences where Trump is being aggressively questioned and usually outright attacked, which then does not bring out his best side.

These 3 Democrats have obviously been personally affected by Democrat policy and "think" - -and have more carefully listened to DJT policy/platform. If I'm wrong about this, I'll post an update.

I'm just so tired of hearing all the emotional arguments against DJT from people who've never taken the time to actually hear what he stands for.

The issue that bothers me the most is when Democrats express their great fear that DJT is out to be a "dictator"! I'd love for someone, anyone, to just walk me through that scenario. Show me where, in the whole of history, someone has suddenly become a dictator at 78 y/o!! Show me where, in the whole of history, someone has become a dictator without military power on his/her side! Show me someone who has never even been in politics for decades who does that. He has the potential of 4 more years - he has made that statement many times and it is just a fact. The "dictator" fear mongering is laughable and the fact that otherwise seemingly intelligent people talk about it is beyond my comprehension. Only someone processing everything emotionally and not logically could come up with that as a concern.

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