For nearly 20 years, Howard Stern has been the crown jewel of SiriusXM’s lineup — a lightning rod for controversy, a master of radio reinvention, and a man whose name has been synonymous with both eye-watering ratings and eyebrow-raising antics.

Now, his historic run may be about to end.

According to a report from The Sun, SiriusXM executives are not expected to renew Stern’s current five-year, $100 million-a-year deal when it expires this fall. While an offer is reportedly on the table, insiders say the gap between what Stern wants and what the company is willing to pay is too wide to bridge.

“Sirius and Stern are never going to meet on the money he is going to want,” one source told The Sun. “It’s no longer worth the investment.”

💰 The Money Problem

At $100 million per year, Stern’s salary has long been one of the most eye-popping in media. But industry insiders say the math no longer makes sense.

SiriusXM is expected to try and keep rights to Stern’s vast digital library — a treasure trove of decades’ worth of interviews, celebrity trainwrecks, and boundary-pushing bits. But the live show itself? That appears to be winding down after a staggering 49-year career in radio.

“There’s no way they can keep paying his salary,” another source said.

📉 Ratings, Relevance, and the Political Pivot

It’s not just the money. Sources tell The Sun that SiriusXM executives have grown weary of Stern’s increasingly political — and divisive — on-air persona.

The man once branded as “The King of All Media” built his empire on shock value, sex jokes, celebrity humiliation, and the kind of irreverent comedy that terrified the FCC. But in 2020, Stern shifted sharply into political commentary, particularly during the COVID-19 pandemic.

That shift didn’t just alienate part of his audience — it reportedly frustrated the very executives who once banked on him as the voice of the “anti-PC” generation.

😷 Stern’s COVID Zealotry

In September 2021, Stern went on a viral rant advocating for mandatory COVID-19 vaccinations, dismissing personal freedom arguments from vaccine skeptics in the bluntest terms possible:

“When are we going to stop putting up with the idiots in this country and just say it’s mandatory to get vaccinated? Fk them. Fk their freedom. I want my freedom to live.”

That same month, he mocked fellow radio hosts who had died after refusing the vaccine:

“Four of them were like ranting on the air — they will not get vaccinated… they were all dying and then their dying words were, ‘I wish I had been more into the vaccine.’”

Critics called the comments callous. Supporters called them honest. Either way, the backlash was loud.

🗳️ Politics on Overdrive

By the 2024 presidential election cycle, Stern’s political commentary had become a staple — and a sore point.

His interview with Democratic nominee Kamala Harris was one of the most high-profile of the campaign, but it also cemented accusations that Stern had gone all-in on partisan politics. In the weeks before the 2020 election, he made it clear where he stood:

“I don’t hate Donald… I hate you for voting for him, for not having intelligence. For not being able to see what’s going on with the coronavirus, for not being able to see what the Justice Department is doing. I hate you, I don’t want you here.”

For SiriusXM executives, this wasn’t the Stern they had signed in 2006 — the irreverent rebel who once mocked all politicians equally.

📻 From WNBC to “K-Rock” to Satellite King

Stern’s journey to SiriusXM was the stuff of broadcasting legend. Starting in the late 1970s at WNBC before becoming the face of New York’s WXRK “K-Rock”, The Howard Stern Show exploded into syndication in the 1990s.

Battles with the FCC over indecency fines became part of the brand. Stern’s show was raunchy, offensive, unpredictable — and for millions, utterly addictive.

In 2006, when he jumped to the then-fledgling Sirius Satellite Radio, the move was seen as a gamble. It paid off, with Stern helping to drive subscription growth and becoming the face of the new medium.

🏦 But Now… the Endgame

Satellite radio itself has changed. The rise of podcasts, streaming audio, and on-demand content means SiriusXM is competing in a far more crowded arena. And Stern’s numbers — while still strong — aren’t delivering the return they once did.

Industry observers note that Stern’s show has become more sporadic, with fewer live episodes and long breaks between fresh content. Combined with the political tone shift, some insiders believe the show has drifted from the must-hear status it once enjoyed.

📺 A Pattern Across Media?

The looming end of Stern’s SiriusXM era comes on the heels of another high-profile cancellation: CBS’s announcement that The Late Show with Stephen Colbert will end next year.

Both Stern and Colbert’s shows became increasingly identified with hyper-partisan political commentary — and both have faced mounting costs and shrinking returns.

“There’s a real conversation happening in media right now about whether politics-heavy entertainment is sustainable,” says media analyst Brooke Jennings. “Stern and Colbert were both dominant forces, but the economics and audience appetite have shifted.”

🗣️ What Comes Next for Stern?

If Stern walks away this fall, the question becomes: what’s next?

Some speculate he could launch his own subscription-based digital platform, cashing in on his brand without corporate oversight. Others believe he may simply retire, focusing on his extensive art collection, philanthropy, and private life in the Hamptons.

But for a man whose career has been defined by reinvention, a total exit seems unlikely.

🔚 Final Thought

If this is the end of The Howard Stern Show as we know it, it closes one of the longest — and most controversial — chapters in broadcasting history.

Howard Stern has been called a genius, a provocateur, a sellout, and a truth-teller — often in the same breath. His rise mirrored the era when “shock jock” radio could command headlines, millions of listeners, and nine-figure contracts.

Now, as SiriusXM reportedly prepares to let him go, Stern faces the same reality that comes for every broadcasting giant: the audience changes, the industry changes, and no one — not even the King of All Media — is immune.