The most valuable newsletter in the universe (no, not this one, unfortunately)

The Free Press is reportedly in line for a $150–$200 million acquisition, a deal that could mark both peak content and the start of a consolidation cycle.

I’m decent at pattern recognition and adaptation. Give me a membership problem and I’ll help you design something that works; ask me to map the forces reshaping media and I can usually trace the currents. But I’m not a trendsetter, and I rarely spot the next hot thing years out.

Bari Weiss has been the odd exception. In the mid-2010s I was already the annoying editor sharing stuff about the latest Weiss-adjacent dust-up on Twitter with my newsroom, true insider baseball most insiders sensibly ignored. I didn’t predict she’d become a cultural/political/media reference point; I just found the constant commotion fascinating.

So when reports surfaced that The Free Press (TFP) was in talks to sell for something like $150–$200 million and that Weiss might land in a senior role at CBS News, I felt an irrational flicker of “called it”. Not because I foresaw this exact outcome, but because some of the underlying mechanics: strong voice & perspective + conflict as means of building a community and turbocharging distribution felt like a sensible (if a little opportunistic) play from relatively early on.

Today I want to explore how her and the Free Press became the world’s most valuable newsletter, what this could mean for the sector and why so many “niche rebellions” may end up as corporate property.

A newsletter worth its weight in Californium-252

First, a quick look at the reported deal: CBS’s parent (Paramount Skydance) is said to be negotiating to buy The Free Press for something in the $150–$200 million range (cash/stock mix, not confirmed) and to install Bari Weiss its founder end chief editor in a decision-making role at CBS News. NYT suggests talks are active, with one sticking point being how long Weiss is willing to commit. (For $150 million, I’d sign in blood, inside of a flaming pentagram, alas, no one’s asking.)

The two organizations could not be more different from each other.