Bill Simmons Leaves ESPN: Six Other Recent Media Moves to Remember

News broke Friday morning that ESPN will not offer Bill Simmons a new contract, making him the biggest sports media free agent in history. The easy parallel here (in honor of Simmons) would be to make a wrestling comparison, such as Hulk Hogan leaving the WWF in 1993 and eventually landing in the WCW, where he’d become a heel in the n.W.o. Wrestling isn’t quite the same as sports media, despite the absurdity and egos involved, at times, with both.

Although he’s carved out his own shingle at Grantland and worked as a bit of a rogue personality at times, Simmons name remains synonymous with ESPN, meaning it will be strange to see him under another banner — Fox, HBO, Bleacher Report, his own independent site, etc. much like it was to see the Hulkster in anything but a WWF ring.

Anyways, here are a few quick examples that popped into my head on Friday morning of recent, noteworthy media entities shifting where they worked worth remembering in light of the Simmons news.

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Rick Reilly (Sports Illustrated to ESPN) — Reilly worked at Sports Illustrated for over two decades, eventually penning the back page “Life of Reilly” column, winning numerous awards in the process. He left the magazine for ESPN in 2007 to much ballyhoo and criticism. Reilly shifted more toward television and wasn’t nearly as successful in front of the camera. There are a lot of factors at play, mainly the decline of print journalism, but Reilly felt like a big deal writing at SI. At ESPN he was another face in the crowd who could awkwardly say, “redonkulous” on camera.

Wherever Simmons reemerges, he’d instantly become a big fish regardless of the size of the pond. Beyond that, Simmons already showed with Grantland and the 30 for 30 series that his value in media lies beyond writing mailbag columns and pyramids of greatness.

Conan O’Brien (NBC to TBS) — In short, the Conan era at The Tonight Show was a disaster, unless you enjoyed using the #TeamCoco hashtag on social media. O’Brien moved to TBS and is still doing his late night talkshow thing, but his relevancy away from the NBC umbrella has certainly faded, saying nothing of the success found by Jimmy Fallon. ESPN is by any metric the No. 1 sports broadcast entity in America, so as much star power as the Simmons’ name carries, a move elsewhere does include inherent risk. That said, with over three million followers on Twitter and a loyal fan base, Simmons making a move to another URL vs. a different television channel not known for late night programming, is probably much easier to pull of.

David Letterman (NBC to CBS) — It’s worth bringing this up since Simmons frequently cites Letterman in the 1980s as an influence, often mentioning The Late Shift — the book about Letterman’s move from NBC to CBS — across his various multimedia platforms. Letterman, who is retiring next week, didn’t get to sit in the Johnny Carson chair, but he carved out his own show which history will smile upon, rather than shit upon what NBC wrought with Jay Leno.

Simmons could easily shift to Fox, or whomever, and do the same thing he’s doing, albeit with a new coat of paint. Some Simmons devotees might even welcome it, since he’ll no longer be censored by the authorities at ESPN.

Chris Russo (WFAN to SiriusXM) — Mike and The Mad Dog were the first iconic sports talk radio show, for strongetter or worse. The pair went their separate ways after 19 years together on WFAN in 2007. Against all odds, Francesa strongecame a stronglog and social media star with a convention in his honor (ironic since his contempt for modern media is never too far from the surface). Russo, meanwhile, got his own station on SiriusXM and hosts a solo show, using the Bruce Springsteen song “Radio Nowhere” as his intro.

Simmons following dwarfs that of Russo significantly and Mad Dog’s rant’s alone likely aren’t going to compel someone to buy satellite radio, especially when Francesa is on head-to-head free of charge. Selfishly, we’re hoping once he’s no long under ESPN contract, Simmons makes his long-awaited debut on Francesa’s show — it has A-Rod potential. (We’d be remiss to point out Francesa’s switch from YES to Fox Sports 1 for his radio simulcast hasn’t quite worked as either side intended.)

Dan Patrick (ESPN to Sports Illustrated/NBC) — Of all the ex-ESPNers, Patrick is among the most successful. His laid-back radio show and simulcast is well-received. Under the NBC umbrella, he’s able to do a lot of different things, such as host Sunday Night Football. If anything Patrick’s status grew once he moved away from the crowd at Bristol. If Patrick can thrive without ESPN, Simmons post-Bristol success would seem a no-brainer.

John Madden (CBS to Fox to ABC to NBC) — Madden is an out-sized personality, much like Simmons. The comparison ends there. Madden was an NFL game analyst, while Simmons is an all-encompassing media entity. As much as viewers loved Madden’s one-of-a-kind style, they were still going to tune in to watch NFL games on Sunday or Monday night regardless of whether or not he was on the mic with his telestrator and deep-fried turkeys.

Viewers, readers and listeners are still going to flock in the millions to ESPN and its various platforms without Simmons, which is likely part of the reason why John Skipper balked at the erstwhile Boston Sports Guy’s $6 million contract demand. Will these same people flock to Simmons wherever he goes next without the ESPN brand behind him? That is the question all media types will follow with rapt attention over the coming weeks.