Jon Gruden has been out of the NFL head coaching ranks for nearly 10 years and he has become one of the top analysts in football. Despite his success with ESPN, it always seemed like Chucky would eventually return to NFL coaching. The Oakland Raiders had 100 million reasons to make this a reality.

The deal to bring Gruden back to the Raiders will be official on Tuesday, when he will be introduced at a news conference. The 54-year old coached in Oakland from 1998-2001 and his new deal could include an ownership stake in the team.

Despite cashing in on the largest deal ever given to an NFL head coach, the big question surrounding Gruden will be if he can still deliver results to the Raiders that would include a trip to the Super Bowl. He was 40-28 (including the playoffs) the first time he coached Oakland, but he did endure a pair of subpar seasons later in Tampa Bay. He will be inheriting a team that has a great young foundation and clearly underperformed this season for Jack Del Rio, who was fired after the regular season. It will be fun to watch Gruden back on the sidelines and he is the perfect head coach for a franchise that will be moving to Las Vegas in 2019.