Jon Rosen: The Unsung Counselor Behind Stephen A. Smith’s ESPN Deal

Missing from most discussions about whether ESPN’s Stephen A. Smith would stick with the Disney sports giant during months-long contract renewal talks was the name of the counselor advising the popular TV host. That’s just the way that Jon Rosen, one of Smith’s business consiglieres, likes it.

Rosen never spoke publicly about the haggling that took place between Disney and Smith, but played a key role in negotiating a deal that gave the sports host the ability to work not only for multiple Disney units but also some properties that Disney doesn’t own.

“My deal was incredibly complicated,” Smith tells Variety in a recent interview. While many observers may have focused on the financial aspects of the deal — reports put his new salary as high as $20 million per year — Smith was more interested in new freedoms. “I wanted the right to go beyond the world of sports,” he says. “To have my own podcast rights, my own audio rights. The freedom to extend beyond the parameters of sports” was “obviously, very pivotal to me,” he explains. “I was going to walk away from ESPN, and that’s not something I wanted to do. That was something I was willing to do” to gain new opportunities, he says. Smith has recently turned up on the NewsNation cable outlet and in ABC’s “General Hospital.” “Jon was in the middle of all that.”

He is likely to be so again soon. Rosen, formerly a longtime executive at WME, struck out on his own in 2024 and launched a new talent-advisory firm, Evolutionary. Among his clients are baseball great Alex Rodriguez, “Good Morning America” co-anchor Robin Roberts, celebrity chef Bobby Flay, and news anchors Willie Geist and Stephanie Ruhle, who have held jobs with both MSNBC and NBC News. As the media world grows more fragmented, with mainstream networks jockeying for talent alongside creator-led venues, Rosen is among those advocating for hosts and anchors to identify different aspects of their abilities and develop them via an array of outlets, not just at a single company.

“The media world today is far more fluid than it used to be — companies that were once competitors are now frequent collaborators,” Rosen says. “One of our main focuses is to help clients see their careers as intellectual property platforms. Exclusivity has a new meaning; it’s about building a strategic blueprint that allows our clients to thrive across multiple verticals simultaneously.”

In years past, such an idea might have been an anathema. But in recent months, more media outlets have proven open to flexible arrangements. At Amazon Prime Video, for example, all the top names involved in presenting “Thursday Night Football” on screen have multiple employers. Kirk Herbstreit, for example, co-hosts the games but maintains a big role tied to college football at ESPN. Michael Strahan co-anchors “Good Morning America” for ABC News, but also serves a critical role at Fox Sports during NFL season.

Others are testing these waters. Steve Kornacki, once a popular presence on MSNBC who is represented by another independent agent, Olivia Metzger, recently entered a new arrangement that has him contributing to NBC News and NBC Sports while able to strike out on his own for outside subjects.

Even Rosen must be flexible. Some of his clients, including Smith, maintain ties to WME. But having his own company means he can work with executives at other agencies, including CAA and UTA, if need be, and move into non-traditional areas of business. He has worked with marketers including Subway, Citizen Watch Co. and Flamingo Estates in recent months as an advisor. And he has worked with the owner of the true-crime series “Forensic Files,” which fills the schedule of Warner Bros. Discovery’s HLN cable network with repeats. After a new round of negotiations, the series can also be seen on NBCUniversal’s Oxygen. Meanwhile, Rosen and the series’ backer, Content Partners, are in discussions about launching a modern version of the program, which first debuted in 1996 on TLC and ran in originals until 2011.

He may have more work to do. The idea of parceling out a client’s talents, finding the best home for them across an array of media platforms and the companies that own them, is likely to be in high demand in years to come. Comcast, parent of NBCUniversal, is in the process of spinning off many of its cable networks into a separate company, Versant, that is likely to create some interesting choices for people who may work for networks on either side of the looming split. Warner has restructured itself so that its cable networks operate in a separate division from its streaming assets, a move that Wall Street believes could augur a similar transaction. Paramount Global, already under pressure to cut costs, is slated to be acquired by Skydance Media in a transaction that calls for more pressure on finances, which may create an opportunity for similar deals.

Rosen left WME about a year before its primary backer, Silver Lake Partners, took its own parent company, Endeavor, private. As part of the process, at least one of its divisions, its football representation business, will be moved under a new start-up run by longtime leader Patrick Whitesell.

“After 29 incredible years at WME, I felt the time was right to channel my entrepreneurial spirit and launch something new. The entertainment landscape is evolving rapidly, and I saw an opportunity to shape a venture that’s designed specifically for this moment,” Rosen says. “This next chapter is about creatively collaborating with our clients, investing alongside them, and building brands that advance with the speed of the market.”

Since founding Evolutionary, Rosen has had the opportunity to work with clients both traditional and new. He has helped Al Roker, Stephanie Ruhle and Van Jones all renew deals with their current employers. He is working with Julia Fox on a reality series. He is trying to help Philadelphia sports journalist Mike Sielsky develop projects around his recent book about the history of the slam dunk in the NBA; working with soccer player Midge Purce; and developing concepts for food influencer and chef Olivia Tiedemann.

Bobby Flay has been with Rosen for about 20 years and says he stays with him because he keeps an eye on more elements than a current relationship with a media company. “Those deals are more than just signing me to a handful of years and go make TV,” says Flay. Rosen “brings publishing into it, alternate media into it. The great thing about Jon is he wants to make money for everybody. Let’s face it, agents want to make money, period. They want to make money for their clients. But what he does is he thinks about everybody in the game. So he makes sure that if he can get Warner Bros. Discovery to make a deal with me, they feel it’s value-added going forward.”

Alex Rodriguez has counted on Rosen to help guide him through deals at both ESPN and his current home, Fox Sports, where he has teamed with Derek Jeter and David Ortiz for pre- and post-game MLB shows that air during the league’s most important games. “What sets Jon apart from others is that he’s not just focused on the next opportunity — he’s focused on the right opportunity. He’s played an instrumental role in developing my relationship with Fox Sports and guiding how and where I show up on camera,” says Rodriguez. “Whether it’s navigating the broadcast world or thinking creatively about new ventures, Jon is always a step ahead and I’m lucky to have him in my corner.”

With an array of new media venues likely to spur even more splintering of audiences, demand for Rosen’s services are likely to continue. Chances are, however, that he will let his clients get most of the spotlight.