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Gruden v. The NFL Takes a Dark Turn

The former coach’s $150 million lawsuit against the NFL has evolved into perhaps the strangest free speech battle in sports: Can the league deny leaking his emails while simultaneously claiming legal immunity for doing so?

Jon Gruden
Jon Gruden during an NFL preseason game, August 2021. Photo: Brian Rothmuller/Icon Sportswire via Getty Images
Eriq Gardner
July 20, 2026

You might not think of Jon Gruden’s long-running legal battle against the NFL as a free speech case, but the league certainly does. It’s arguably the strangest First Amendment dispute still working its way through the courts: whether Roger Goodell cost Gruden his job as head coach of the Las Vegas Raiders by leaking his racist, misogynistic, and homophobic emails to The Wall Street Journal and The New York Times—and whether, if the NFL actually did that, they were exercising their right to free speech.