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

About this episode

A sharp conversation about political realignment, antisemitism, and why so many young people are drifting toward anger online. In this condensed recap of Keeping It Real, Jillian Michaels talks with Shabbos Kestenbaum about his journey from Obama volunteer and Bernie supporter to conservative critic of the modern left after Harvard and October 7th. The episode examines misinformation, media literacy, free speech, Gen Z radicalization, and the rise of figures like Tucker Carlson and Nick Fuentes. Kestenbaum also weighs in on foreign influence in politics, AIPAC, Qatar’s role in higher education, and why facts have to come before ideology. Hear the key ideas from the original episode in a…