After nearly two decades atop the satellite radio world, Howard Stern’s future with SiriusXM is anything but certain. As his $500 million contract nears its expiration, insiders say the legendary shock jock is weighing his options—and one of them may be walking away for good.

“He’s off for the summer, like usual,” a source told The Daily Mail. “But this year, he’s been saying, ‘Maybe I should retire.’”

That kind of talk isn’t just idle chatter. With the contract set to expire this fall, and SiriusXM’s programming strategy shifting toward newer, younger stars like Andy Cohen, the idea of a post-Stern SiriusXM isn’t as far-fetched as it once was.

For a host who once redefined radio—turning shock and satire into an art form—this could mark the end of an era.

The $500 Million Question

Stern, now 71, inked his most recent five-year contract in 2020. At a reported $500 million, the deal was seen at the time as a reaffirmation of SiriusXM’s loyalty to its biggest star—a talent who had helped build the platform from fringe curiosity to media giant.

But in 2025, SiriusXM is a different company, and so is the media landscape. Podcasts dominate, smart speakers stream seamlessly, and audiences are more fragmented than ever. Amid shifting economics, insiders suggest the satellite giant may no longer be willing—or able—to pay Stern another nine-figure sum.

“He may do a one- to two-year contract if they can meet him where he wants financially,” another source told The Sun. “He doesn’t want to pull the plug on his employees like this.”

But if the money isn’t right?

“He’s considering parting ways,” the source added.

Stern’s Quiet Exit Strategy?

Stern hasn’t directly commented on the reports, but he’s long been candid about the possibility of retirement.

In recent broadcasts, he’s mused openly about whether he’s still “needed,” and whether he has the energy—or interest—for another long contract cycle. He’s joked about the comfort of not waking up early and praised the simplicity of working from home, where he’s been broadcasting almost exclusively since the COVID-19 pandemic began in 2020.

“I don’t miss being in the studio,” Stern said on-air in 2023. “I’ve got everything I need right here.”

But for longtime fans, that’s part of the problem.

A Changing Stern, A Divided Audience

Stern’s identity has always been evolving. Once known for outrageous bits, risqué content, and brutal honesty, he’s become more introspective, more politically engaged—and, depending on who you ask, more “woke.”

He’s interviewed President Joe Biden and Vice President Kamala Harris, leaning heavily into progressive causes. He’s also publicly battled anti-vaxxers and criticized former President Donald Trump, whom he once considered a friend.

This evolution has polarized his fanbase. Some appreciate the growth. Others call him out for what they see as hypocrisy, especially when Stern’s recent interviews with big names have become increasingly safe.

“He used to be fearless,” one media blogger wrote. “Now he’s doing puff pieces from his basement.”

And then there’s the numbers.

From Millions to Thousands

At his peak, Stern’s SiriusXM broadcasts were reportedly reaching up to 20 million listeners daily. In 2025, estimates put that number closer to 125,000.

By comparison, Andy Cohen—whose shows Radio Andy and Andy Cohen Live have gained traction on multiple channels—is said to be commanding significantly larger audiences. That hasn’t gone unnoticed by Stern, who is reportedly “irritated” by the company’s growing focus on Cohen.

“Howard doesn’t like sharing the spotlight,” said one SiriusXM staffer. “Especially not with someone who’s doing the kind of light, breezy entertainment he used to sneer at.”

What Would a Stern Exit Mean for SiriusXM?

Even with his diminished numbers, Stern is still arguably the face of SiriusXM. His archives—decades of celebrity interviews, infamous bits, and unfiltered commentary—remain one of the platform’s most valuable assets.

That’s why, according to The Sun, SiriusXM may be looking to negotiate not just a contract renewal, but a licensing deal that secures the long-term rights to Stern’s content even if he walks away from the mic.

“It’s not just about live shows anymore,” said media analyst Tara McKenzie. “It’s about owning the library.”

And Stern knows it.

His content is evergreen, endlessly clip-able, and deeply tied to SiriusXM’s brand identity. If he leaves, he likely takes part of the platform’s cultural cachet with him.

What’s Next for Stern—and for Satellite Radio?

If Stern does retire, he’d be joining a wave of legacy broadcasters stepping back from the spotlight. Stephen Colbert’s Late Show is ending next year. Jimmy Fallon has hinted at his own frustrations with time-limited interviews. And even icons like Oprah and Letterman have moved into semi-retirement.

The difference? Most haven’t had the same kind of unique ownership over their platform as Stern has with SiriusXM.

“He is SiriusXM, to many people,” said radio historian Matt Cohen. “Losing him—even now—would be like HBO losing Game of Thrones in Season 3. It’s survivable, but the brand changes.”

Meanwhile, SiriusXM is investing more in digital, podcasting, and short-form content. With its recent deal to acquire SmartLess and other major podcasts, the platform appears to be betting on a new generation of talent.

Whether Stern fits into that future remains uncertain.

A Legend’s Legacy—And an Industry at a Crossroads

Howard Stern’s career has spanned over four decades. He’s battled the FCC, redefined free speech in broadcasting, and become both a media mogul and a cautionary tale.

He’s made enemies and inspired imitators. He’s drawn criticism and earned awards. He’s faded and returned, time and again.

Now, as his $500 million contract approaches its final months, the man who once bragged about never needing “corporate suits” may be making his final big decision: to cash in one more time—or cash out for good.

“I’ve had a great run,” Stern said recently. “But I don’t owe anyone anything.”

Conclusion: The End of the Line, or Just a New Frequency?

Howard Stern’s future is uncertain—but it’s also entirely in his hands. Whether he signs a short-term deal, negotiates for archive rights, or walks away entirely, one thing is clear: the Howard Stern Show, as we know it, is at a crossroads.

And so is SiriusXM.

In a media landscape where stars now build empires from their living rooms, where podcasts rival networks, and where even legends must reinvent themselves, Stern’s next move may determine more than just his own legacy.

It may decide whether satellite radio can survive without its original king.