Jon Gruden OAKLAND, CA – NOVEMBER 18: Former head coach of the Oakland Raiders and now ESPN Monday Night Football Analyst Jon Gruden looks on during pre-game warm ups before an NFL football game between the New Orleans Saints and Oakland Raiders at Coliseum on November 18, 2012 in Oakland, California. (Photo by Thearon W. Henderson/Getty Images)

For years, as Jon Gruden’s name popped up in coaching rumors, the former Super Bowl-winner doggedly insisted he was perfectly happy at ESPN. The annual dance long begged the question: What would it take for Gruden to leave broadcasting?

Well, we now have our answer. On Friday, ESPN’s Adam Schefter reported that the Raiders will pay Gruden $100 million over 10 years to be their head coach. Not only will that make him the NFL’s highest-paid coach, it will also place him in line with the NFL’s highest-paid players.

The Raiders still have not officially announced Gruden as their new coach, though the hiring was first reported nearly a week ago and Gruden himself has acknowledged there is a “strong chance” he will end up in Oakland.

You could argue that no coach deserves a contract of the size Gruden is getting, but this deal seems especially outlandish given Gruden hasn’t coached since 2008 and went only 57-55 over seven seasons with the Bucs in his most recent gig. He seems to be coasting on his success with the Raiders in the early 2000s and his Super Bowl championship with Tampa a decade and a half ago. Even if Gruden is able to adapt to a league that has changed plenty since he last held a clipboard, there’s limited evidence that he can be the franchise-changer his contract suggests he will be.

Though the Raiders might eventually regret hiring Gruden at this price, ESPN will surely be sad to see him go. In nine years at the network, Gruden became a Monday Night Football staple and carved out a niche as a catchphrase-loving football guru. Not only will ESPN have to replace him in the broadcast booth (Peyton Manning? Tim Tebow? Ron Jaworski?), it will have to fill a void left by his “Quarterback Camp” schtick and various other segments.

It always seemed inevitable that Gruden would leave ESPN and return to coaching some time or another. It turned out all he needed to make it happen was $100 million.

About Alex Putterman

Alex is a writer and editor for The Comeback and Awful Announcing. He has written for The Atlantic, VICE Sports,, and more. He is a proud alum of Northwestern University and The Daily Northwestern. You can find him on Twitter @AlexPutterman.