Shannon Sharpe’s life and career have been going downhill ever since the s**ual assault lawsuit filed against him. The seriousness of the issue, even without a verdict, has taken a toll on everything he has built.
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Sharpe has already stepped away from his regular appearances on First Take alongside Stephen A. Smith. But the damage didn’t stop there. He reportedly lost a $100 million podcast deal that was in the pipeline for his Shay Shay Media.
The new deal would have encompassed his entire Shay Shay Media empire, including Club Shay Shay, Nightcap with Chad Johnson, Club 520 Podcast, The Bubba Dub Show, and Humble Baddies. As things stand, he remains contract-less since his previous deal with Colin Cowherd’s The Volume podcast network ran out this year.
Sharpe finally opened up about his media future during a candid conversation with Barstool Sports owner Dave Portnoy. While the NFL legend may no longer be catching passes on the field, he’s still very much a free agent in the sports media world. And who better to pitch himself to than the head of a $500 million media empire?
On the latest episode of Club Shay Shay, Sharpe subtly pushed forth the idea that he’s open for business. He hinted that he’s willing to explore opportunities with major media platforms like Barstool.
“Ya’ll pay. Pay pay. I’m a free agent. Dave, I’m just throwing it out there. We don’t have to negotiate publicly, I’m just saying, I’m free whenever you want me to be. No parole, no probation, nothing. I mean free,” said Sharpe.
Portnoy responded by defending his company’s reputation, asserting that Barstool pays its talent well, contrary to popular belief. Curious about the bait, Portnoy then asked Sharpe what being a “free agent” actually means in his current situation.
Shannon leaned into the term, calling himself a “free man” and suggesting that Dave should be willing to roll the dice on him. The message was clear: Sharpe isn’t locked down — and he’s ready to talk.
Then came the hypotheticals, as Portnoy began entertaining the idea of bringing the Hall of Famer on board. He was speculating on how Sharpe might fit into Barstool Sports’ unique business model.
Portnoy was upfront that he wouldn’t be the one to elevate Shannon in the media world — and how could he? Sharpe is already a major force in sports media.
Barstool, he explained, doesn’t usually go after big personalities. Instead, they prefer to develop homegrown talent from the ground up.
“Our model is generally the reverse. We find the guys and build them up, and then they leave. You’re coming to us, for example- We’re not going to make you bigger. You’re huge,” said Portnoy.
Our secret sauce is: If you are talented, we’ll make you huge. I’m not a big negotiator. I have a price that works for us, and if that’s not good enough, what are you going to do? He asked.
The conversation then moved on to fresh talent. Since Portnoy has a reputation for spotting uncut gems, Shannon naturally asked him for his two cents on who he believes is the next big thing in sports media.
After giving it some thought, Portnoy couldn’t name anyone off the top of his head. But when it came to underrated talent, he did highlight what he considers Barstool’s best recent hire — former Las Vegas Raiders head coach John Gruden.
Portnoy praised Gruden as a natural. He called him a total package — full of personality, charm, and the kind of presence that can command a room. According to Dave, Gruden has all the tools to thrive in sports media.
As for Shannon, while he’s currently earning over $5 million from ESPN, he’s clearly looking for a new platform to rebuild his brand. Portnoy might be able to land Shannon on a cut-price deal.
But to pull that off, he’d have to stray from his usual approach to negotiations. Sharpe would be a massive get for Barstool — someone who speaks his mind and thrives with creative freedom, which is exactly what the Barstool brand offers.
In the end, it’ll likely come down to one thing: The dollar amount and the outcome of Shannon’s legal situation.
