Bill Simmons Could Be The Biggest Sports Media Free Agent of 2025: Report

The most intriguing sports media free agent of 2025 is not a play-by-play announcer, an analyst, or even a postgame host.

Defining Bill Simmons’ role in the sports media universe is a tall order, but he could have free rein to chart his own journey beginning in 2025.

According to a report in the New York Post, Simmons’ contract with Spotify is set to expire in 2025. Why would Simmons abandon the company that paid $250 million for his own venture, The Ringer, just four years ago?

According to the Post’s Ryan Glasspiegel, Simmons has had “exploratory conversations” with other companies about the possibility of launching a new platform:

Sources said that Simmons has privately expressed frustration with confidants about Spotify’s corporate structure in which he has not had full personnel autonomy to bring all of the talents or shows that he wanted to add to the fold.

Nonetheless, Simmons and Spotify have had an ongoing dialogue about the possibility of a new deal.

Simmons, through a spokesperson, informed the Post that this rumor amounted to “incorrect and idle speculation.” For its part, Spotify told the Post it has no plans to sell The Ringer.

The Ringer was among the many investments Spotify made in a broad podcast portfolio. Among other prominent hosts on the app are Barack and Michelle Obama, Joe Rogan, “Call Her Daddy” host Alex Cooper, and Prince Harry and Meghan Markle.

But Simmons has never been a fan of corporate oversight, dating to his days as a protoblogger on ESPN’s Page 2, where he proudly touted his contrarian views without access on a platform known for giving its audience a front-row seat to live sporting events.

Simmons’ time at ESPN ultimately was precipitated by critical comments of NFL commissioner Roger Goodell. In 2014, ESPN suspended Simmons — then among its highest-profile personalities — three weeks for calling Goodell a liar. Simmons said he thought Goodell lied about not knowing what was on a security video that showed former Baltimore Ravens running back Ray Rice hitting his wife in an elevator. He left ESPN the following year.

On Spotify, some of Simmons’ podcasts launched prior to the sale of The Ringer were ultimately discontinued, which could speak to his desire for greater personnel autonomy.

Guessing Simmons’ next venture — if there is one — would be tantalizing. Few saw the arrival of “30 for 30,” Grantland.com, or The Ringer coming before he helped launch each project. Yet in each case Simmons masterfully demonstrated his eye for talents and trends on the rise, before they reached public prominence.

With or without Spotify’s help, it’s a safe bet Simmons will do the same again.