In this Substack Live, David speaks with Sarah Matthews, former Trump White House deputy press secretary, about an escalating clampdown on speech and why legacy institutions are buckling. They walk through the Colbert cancellation, Jimmy Kimmel’s indefinite suspension, and the public pressure campaign led by FCC chair Brendan Carr as examples of how lawsuits, merger leverage, and informal threats can chill comedy and journalism before anything even goes to court. Both argue the next logical target is independent media—shows and creators on YouTube and podcasts—because that’s where audiences are now.
The conversation widens to the Trump White House press operation and the present drought of briefings under press secretary Karoline Leavitt. Matthews suggests the administration is avoiding questions it least wants to answer, like the Epstein files and the president’s health, while still claiming “transparency.” She also reflects on how Trump-era conservatism flipped core free-speech principles on their head.
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