Bari Weiss

Bari Weiss is the mirror image of the tech figures^[1] we spent most of the first episode on. They started from power and convinced themselves they were outsiders. She was an outsider inside the progressive consensus, and she built an institution out of being pushed out of it. Her 2020 resignation letter from The New York Times became the founding story. Common Sense became The Free Press, and as I discussed on the show, Paramount Skydance acquired it and named her editor-in-chief of CBS News^[2].

She deserves substantial credit. She built a large independent outlet from scratch, she gives a platform to people who don't fit a party line, and her politics are genuinely her own mix: pro-choice, married to a woman, fiercely pro-Israel, skeptical of school lockdowns, a self-described radical centrist. Friends and critics alike describe rare personal charisma.

My critique is about the engine. Her audience was built on the grievance of being punished for deviating. That's the same emotional fuel that powers Sacks and Andreessen, just from the opposite side of the table. Grievance is good at seeing what's wrong with an institution. It's bad at running one. Now she's inside the kind of legacy institution she spent years attacking, and the reported staff friction at CBS reads to me like that tension playing out. I also noted that The Free Press has run a string of pieces attacking Zohran Mamdani. That's legitimate opinion journalism, but it's worth watching whether the skepticism is symmetric.

I don't doubt her sincerity. The open question, as I put it on air, is whether sincerity survives contact with power. One uncertainty: her role is reportedly in flux amid the merger. Evidence that CBS under her holds allies to the same standard as opponents would move me toward the more generous read.