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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

Jon Gruden

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.

Gruden grew up in Ohio as a Cleveland Browns fan and was the backup quarterback for the University of Dayton Flyers in the early ’80s, playing sparsely. In 1986, he landed his first coaching job as a graduate assistant with Tennessee.

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To kick off the college football season here’s Jon Gruden suiting up for the #Yers


After a brief stop in Missouri, Gruden headed out to California and landed his first NFL job shortly thereafter, serving as an assistant to the San Francisco 49ers quarterbacks coach Mike Holmgren. It was Joe Montana’s final season as the starter.

Two years later, Gruden followed Holmgren to the Green Bay Packers, where he eventually rose to wide receivers coach. In 1995, he was hired as the Philadelphia Eagles’ new offensive coordinator.

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Holmgren, Jon Gruden, Steve Mariucci, Ray Rhodes, Andy Reid all in this picture.


See the rest of the story at Business Insider

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