Jon Gruden is set to sign a deal with the Oakland Raiders that will pay him $100M over ten-years. And I’m not sure if this is great for the Raiders organization or if Jon Gruden is stealing money from a struggling franchise.

Jon Gruden hasn’t coached a game since 2008. That was ten years ago. And when he did coach, you could argue that his career was pretty mediocre. He coached for ten-years and only had four really successful seasons.

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He went 22-10 in his final two-years with the Raiders. Gruden was then traded to the Buccaneers and won a Super Bowl in his first season with the team. But then had only one other really good year in Tampa when they went 11-5 in 2005.

Besides those four-seasons, Grudens win-loss record is 50-62. When he was with Tampa Bay the Buccaneers had three losing seasons. In those three-seasons the team went 16-32. So it’s tough for me to say that this is a great signing.

Like everyone, I love Gruden. He’s a personality and that’s really shown on his stint with Monday Night Football. He obviously loves the game and knows his stuff. But despite his rebuild in Oakland, his biggest success came from a team he inherited.

He didn’t build the Buccaneers. In fact he took over an already playoff proven team and essentially helped them get over the hump. The Buccaneers had an all-time great defence but didn’t have the offensive game-plan to back it up.

Jon Gruden and his spider-2-y-banana, or whatever his famous play is called, helped secure a Super Bowl for that Hall of Fame defence. However, Tampa followed that Super Bowl with back-to-back losing seasons. So you could argue that Gruden tore that team apart.

I don’t love this deal. I think Gruden is a guy worth taking a shot on. Especially considering that Gruden is a quarterback guru and will be inheriting an amazing young talent in Derek Carr. But $100M over ten-years is a long contract for a guy who hasn’t coached in that same amount of time.