How Jon Gruden turned coaching success into huge paydays from ESPN — all while being one of the most sought-after coaching candidates in the game

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Nearly a full decade after calling his last play as an NFL head coach, Jon Gruden remains one of the biggest names in professional football.

After leading the Oakland Raiders to back-to-back division titles in 2000 and 2001, Gruden was flipped to the Tampa Bay Buccaneers in a blockbuster trade. There, he became the youngest Super Bowl-winning head coach in history.

Since Gruden’s coaching days ended, he has been an analyst on “Monday Night Football,” as the highest-paid employee at ESPN. Still, it seems that almost every time there is a high-profile opening for a head coach, his name is among the first to be mentioned.

Below, take a look back at Gruden’s wild ride through 30 years of playing, coaching, and talking about football.