Keeping It Real: Shabbos Kestenbaum on Leaving the Left and the Woke Right

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When politics, identity, and online rage collide, the result can be explosive. This episode of Keeping It Real features Jillian Michaels sitting down with Shabbos Kestenbaum, the young Jewish activist and PragerU commentator, whose journey from the left to the Republican National Convention reveals a lot about our current fault lines. And what a journey it's been. Kestenbaum's political history is fascinating. He was knocking on doors for Barack Obama as a child, volunteering for Cory Booker, marching with Black Lives Matter, even showing up at the 2016 Democratic Convention as a Bernie supporter.

Right, but then something shifted dramatically. At Harvard, and especially after October 7th, he says the left lost him completely. The breaking point was seeing elite progressive groups react to Hamas's attack by blaming Jews instead of condemning the massacre.

That's when he turned toward conservatism, though he's careful about labels. He doesn't call himself fully conservative because he's not religious and is gay, but he says he's found more openness on the right than expected. His message is pretty clear: "We should encourage people who were liberal to join the movement." And Michaels agrees with that, emphasizing the conservative coalition needs room for different backgrounds, as long as people share core principles. But things get really sharp when they discuss the so-called woke right and figures like Nick Fuentes and Tucker Carlson.

Kestenbaum doesn't hold back there. He argues that some figures inside the Republican world aren't really conservative at all. He's particularly concerned about Fuentes, saying he's dangerous because he identifies real problems among young people, like loneliness and purposelessness, but offers poisonous answers.

Exactly. Kestenbaum says, "We cannot surrender that territory; we have to meet people where they are." But he warns that charismatic extremists can lead people toward antisemitism and isolation.

What about the foreign influence debate? Interesting point there. He rejects claims that AIPAC is an Israeli front, noting it's made up of Americans, though he supports broader limits on money in politics. But he does point to Qatar's large spending on U.S. higher education as overlooked foreign influence. His principle is simple: "We can debate opinions, but we cannot debate facts." The conversation then widens into a larger warning about Gen Z men, social media, and political violence. Kestenbaum sees many young men as lonely, disconnected, and vulnerable to radical voices on platforms like TikTok and Twitch. And his solution goes beyond just politics. He argues for healthier communities, stronger institutions, and more meaning in daily life. He closes with a powerful point: the country needs leaders who are factual, consistent, and willing to pull young people back from anger before it becomes something much worse. It's a conversation that touches every major cultural fault line we're facing right now.