Nov 9, 2026 · 26 min
The Times weighs an AI windfall and a Letterboxd-sized bet
Media Monday: Hollywood’s Midterm Hangover & Times M&A Fantasies
The episode connects a consequential publisher-versus-AI copyright fight to the strategic choices that could reshape the Times.
- 1Democrats’ investigative control could expose communications involving media executives, the White House, Paramount, and Nexstar.
- 2The Times’ copyright case against OpenAI and Microsoft could produce a major settlement and encourage similar publisher claims.
- 3A windfall could push the Times toward scalable consumer businesses such as games, education, language learning, or Letterboxd.
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Hamby’s recorded correction reveals that the Times had entered late-stage talks to acquire Letterboxd for $330 million, validating Kelly’s earlier speculation.
The brief
Jon Kelly and Peter Hamby begin with election-night television, arguing that ratings reflected audience habits as much as network execution while praising CNN’s post-election reporting and bookings.
With Democrats controlling investigative committees, Hamby outlines potential scrutiny of Trump-aligned media and corporate executives; Kelly counters that many acted according to perceived fiduciary interests.
The hosts examine what enforceable congressional subpoenas could reveal about Nexstar, the White House, Paramount, Jimmy Kimmel, and CBS’s 60 Minutes interview with Kamala Harris.
The New York Times’ copyright case against OpenAI and Microsoft becomes the episode’s financial hinge: a major settlement could fund expansion well beyond traditional news.
Kelly imagines the Times pursuing scalable consumer niches including games, education, language learning, Wirecutter, and Letterboxd, while Hamby’s correction notes late-stage talks to buy Letterboxd for $330 million.
The Letterboxd news turns Kelly’s speculative acquisition list into an unusually timely prediction, crystallizing the broader question of how a publisher should deploy an AI-era windfall.
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