Rumors are swirling: Is The Howard Stern Show about to end when the King of All Media’s record-shattering SiriusXM deal expires this fall? With reports hinting at a contract standoff—and Stern’s possible exit—the focus has shifted not only to his career but also to the staggering property empire he’s built with his fortune.

Contract Countdown and Speculation

Stern’s current five-year, $500 million SiriusXM contract is set to expire in fall 2025. While Sirius insiders reportedly plan to make an offer, sources suggest it won’t meet Stern’s price. One insider claims, “It’s no longer worth the investment.” Others say the political climate—and Stern’s outspoken views—may also be factors.

Listener Numbers in Question

When Stern joined Sirius in 2006, his audience was measured in the millions. By 2020, estimates put it at 2.7 million subscribers, but some outlets claim that number has plunged to around 125,000. If true, this drop could be a major negotiating point.

Building a Real Estate Empire

Stern’s radio reign has funded one of the most jaw-dropping property portfolios in entertainment:

Palm Beach Palace – Bought for $52 million in 2013, plus $13 million in renovations. This 19,000-square-foot, beachfront estate boasts five bedrooms, 12.5 bathrooms, and a 1,000-square-foot closet for his wife Beth.

Southampton Sanctuary – Purchased in 2005 for $20 million, now worth an estimated $51 million. Spanning 15,000 square feet on 4.25 acres, it features a bowling alley, wine cellar, spa, and a 1,500-square-foot master suite.

Manhattan Manor – A two-story, 8,000-square-foot penthouse composed of five combined condos on the 53rd and 54th floors of Millennium Tower, purchased over a decade for a total of $21 million.

Remote Broadcasting from Paradise

Since the pandemic, Stern has largely avoided the SiriusXM studios, opting to broadcast from his lavish homes. With his properties offering luxury and privacy, it’s no surprise that he’s comfortable working—and potentially retiring—from these retreats.

The Legacy Question

At 71, Stern’s influence spans over four decades, from dominating FM radio to pioneering subscription-based satellite broadcasting. If he walks away, it could mark the end of an era for shock-jock radio.

What’s Next?

Stern could take a shorter-term deal, jump to a new platform, or retire to his multimillion-dollar estates. Until he or SiriusXM confirms the plan, fans and critics are left waiting for a decision that will ripple across the media world.

One thing’s certain: whether on-air or off, Howard Stern has already built his empire—and he’s not leaving the spotlight quietly.