NEW YORK — The self-styled “King of All Media” may be nearing the end of his reign on satellite radio.

Howard Stern, 71, is in “very serious negotiations” with SiriusXM as his $500 million, five-year contract ticks down toward its final months, according to multiple insiders who spoke to the Daily Mail. After nearly two decades as the crown jewel of the platform, the shock-jock’s next move is uncertain — and the decision could reshape the future of the Howard Stern Show and the 95-person staff that produces it.

Negotiations at a Crossroads

Stern has hosted the second incarnation of The Howard Stern Show on SiriusXM since 2006, building on a run that began in 1986 on terrestrial radio.

One source close to the talks says the veteran broadcaster may opt for a shorter one- or two-year extension “if they can meet him where he wants financially.” The priority, this insider claims, isn’t just Stern’s pay — it’s also not “pulling the plug” on the large team of writers, producers, and engineers who keep the show running.

Another source was blunter: Stern is “considering parting ways” with SiriusXM entirely, possibly selling the rights to his vast back catalogue for replay on the network’s uncensored Howard 100 and Howard 101 channels.

For now, his staff has only recently been looped in on the possibility that the end could be near.

From Fearsome to ‘Irrelevant’?

The stakes are as much about legacy as they are about money. Stern’s career arc has taken him from the most feared interviewer in American entertainment to, in Kanye West’s recent words, “an irrelevant old man.”

Once commanding audiences of more than 20 million a day, Stern’s listenership has reportedly fallen to as low as 125,000 in recent years. Fans and critics alike point to his long-term decision to broadcast from home — citing COVID-19 fears — as one factor in the decline.

The shift has been matched by a public repositioning. In 2023, after critics claimed he had “gone soft,” Stern declared on-air:

“I kind of take that as a compliment, that I’m woke… If woke means I can’t get behind Trump… or that I support people who want to be transgender or I’m for the vaccine, dude, call me woke as you f***ing want.”

The remarks won him praise in some circles and backlash in others, especially among fans nostalgic for his unfiltered, taboo-breaking heyday.

Competition Inside the Building

Complicating matters: reports that Stern is displeased with SiriusXM’s growing reliance on fellow star Andy Cohen. According to insiders, the company has been “leaning heavily” on Cohen’s programming to drive subscriptions — a shift Stern is said to view with skepticism.

A Career of Unforgettable (and Sometimes Regrettable) Moments

Stern’s ability to pull shocking, news-making quotes from guests helped define his career.

Donald Trump appeared more than 20 times before entering politics, famously making eyebrow-raising remarks about his sex life and, in a 2006 interview, describing daughter Ivanka as “very voluptuous.”

In 2009, Kim and Khloé Kardashian appeared together, fielding Stern’s explicit questions about their dating preferences and sex lives.

His 2019 book Howard Stern Comes Again revealed one of his deepest regrets: never apologizing to Robin Williams for aggressively questioning the actor about his personal life during a 1990s interview. Stern later recognized — through years of therapy — how his narcissism had blinded him to Williams’ feelings. Williams died before Stern reached out.

But the same bluntness has also fueled fierce criticism.

In the 1990s, Stern mocked fans mourning singer Selena by playing gunshot sounds over her music and imitating a Hispanic accent. He once said some of the female students fleeing the Columbine High School massacre were “really good looking girls” and speculated crudely about the attackers. Earlier in his career, he joked that the “closest I came to making love to a black woman” was masturbating to the image of Aunt Jemima.

These comments, replayed and criticized in the era of social-media outrage, have complicated his legacy.

The Rise of the King

When Stern jumped from terrestrial radio to Sirius in 2006, the move was seismic. Unshackled from FCC decency rules, he could broadcast without censorship — and Sirius paid handsomely for the privilege. Over the years, the show became the tentpole of the satellite platform, with celebrity interviews, raunchy comedy bits, and long-running on-air sagas that kept fans glued.

Alongside longtime co-host Robin Quivers, Stern parlayed his radio success into bestselling books, late-night TV ventures, and even a judging stint on America’s Got Talent.

Now, the Question: What’s Next?

Stern traditionally takes summers off, but this year he’s reportedly been telling people “maybe I should retire.”

If he walks away, insiders say he might still return for occasional specials. If he stays, it could be under a shorter contract — giving him flexibility without the grind of a full-time schedule.

There’s also the potential business play of selling his decades-long archive, ensuring fans (and SiriusXM) could relive classic moments even if no new ones are created.

The End of an Era?

Whether Stern re-ups, retires, or pivots to a part-time role, the negotiations mark a turning point. The man who built his brand on never holding back is now weighing how — and if — to keep going in a media environment far different from the one he dominated.

For SiriusXM, losing Stern would mean the end of a 20-year partnership that helped define the service. For Stern, it’s a choice between securing one more lucrative run or leaving on his own terms — before ratings, relevance, or corporate politics make the decision for him.

Either way, the days of the $500 million contract are almost certainly behind him. And for a broadcaster whose career has thrived on having the last word, that might be the hardest adjustment of all.