August 6, 2025 - 7:00pm
Howard Stern is reportedly threatening to walk away from his radio empire amid a breakdown in contract negotiations. “Shock jock Howard Stern’s 20-year run about to end in stunning move that’s left staff blindsided,” blared a Daily Mail headline on Tuesday evening. If he really does pack it in this time, his exit will carry a distinctly Shakespearean air.
The report claims that Stern is mulling retirement now that his five-year contract is up for renewal. The leaks could well be part of a negotiating tactic for the broadcasting giant who, according to the Mail, went “from having 20 million listeners a day to figures fans believe are as low as 125,000”.
Back in 2015, when Stern was being cagey about another contract renewal, Bloomberg explored the market dynamics in a long profile. One section stood out: “On message boards, Stern’s fans are tossing out ideas. He should move to the Internet. Or sign with Apple. Or start a podcast. The breakout popularity of Serial, a 12-episode podcast from the makers of This American Life, inspired more than one trend spotter to declare 2015 ‘the year of the podcast’. In February a caller asked Stern what he thought of the medium. ‘It’s stupid. It’s a waste of time,’ he said. ‘If you want to be in radio, forget a podcast. Podcasts are for losers.’”
Podcasts are for losers! That was spoken by the man who upended radio more than anyone else — just a decade before the “podcast election” swept his longtime guest Donald Trump back into the White House. Stern experimented with the paywall before podcasters perfected it. He nudged the country in a coarser direction, and put one of the first big dents in the media gatekeepers’ wall. All that is to say, this is Stern’s revolution — both culturally and technologically.
What’s happening in late-night comedy is happening across the board. Stephen Colbert can beat his network competitors with a fraction of Johnny Carson’s audience, but CBS can’t sustain his outdated salary and the traditional overhead that comes with such a big production. In a similar vein, Stern gave terrestrial radio the first taste of the competition that podcasts would bring. If the Daily Mail’s audience estimates are correct, Stern may have lost a good chunk of his leverage this time around.
Much has been made of Stern’s transformation from boundary-pushing provocateur to self-proclaimed woke elder statesman. He now openly embraces the label, having conducted fawning interviews with Joe Biden and Kamala Harris, and once pined after Hillary Clinton. His 2019 memoir — written after a cancer scare — cast the shift in a new light. Reflecting on his earlier shock-jock persona, Stern said: “I loved the idea that we’d go on the air and measure our penises or discuss vaginal secretions — whatever it was, if it freaked you out, I loved it because to me it was not a big deal.” He added: “But now I find it gross. And I’d feel really fucking shitty if I hadn’t evolved. I’d be completely out of step with the times.”
That, of course, came during the high watermark of cancel culture. But now that the wave has receded, Stern’s instincts look off. His sense of where “the times” were headed seems just as blinkered as the media elites who mistook the mood inside their professional-class bubble for that of the country at large. Stern, of all people, should have known better. Perhaps it’s no surprise that he may end his career as a victim of his own success.
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