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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Chris Livingston/Getty

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.


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.

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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.


His first year in Philadelphia was a rough one for the offense, but things improved rapidly from there. The Eagles were one of the top five teams in yards gained in both 1996 and 1997.


The following year, Gruden was hired to serve as head coach of the Oakland Raiders, his first such job at any level. At just 35, he was one of the youngest head coaches in NFL history.

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Todd Warshaw/Getty

Source: Pro Football Hall of Fame


Gruden inherited a team that had gone 4-12 the previous season, but he quickly got them going in the right direction. The Raiders went 8-8 in back-to-back seasons to start his tenure.


Despite his sometimes prickly exterior, Gruden was a hit with his players. They playfully dubbed him “Chucky” after the evil doll from the “Child’s Play” movies.


People Magazine took a more charitable view. Gruden was once named to the publication’s 50 Most Beautiful People list.

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Tom Hauck/Getty

Source: ESPN


One of Gruden’s biggest success stories was Rich Gannon, a 35-year-old quarterback with a 75.6 career passer rating through his first 83 games. The journeyman took to the Raiders’ system almost immediately, throwing for 3,840 yards and 24 touchdowns en route to the 2000 Pro Bowl.


In 2000, the Raiders rode their prolific offense to a 12-4 record, ultimately falling to the Baltimore Ravens in the Conference Championship.

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Tom Hauck/Getty

The game was a controversial one. Gannon suffered a big hit at the hands of Baltimore’s Tony Siragusa early in the second quarter, forcing him from the game. Gannon returned in the second half, but he struggled, and the Raiders lost 16-3. Siragusa was later fined $10,000.

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Brian Bahr/Getty

Source: San Francisco Chronicle


Gruden led the Raiders to one more playoff appearance before he was traded to the Tampa Bay Buccaneers for an absolute haul: two first-round draft picks, two second-rounders, and $8 million. Gruden’s parents lived in the area, leading to speculation that he had pushed for the deal.

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Peter Muhly/Getty

Source: Los Angeles Times


He hit the ground running with his new team, which had made the playoffs in three straight seasons but won just two games. The Buccaneers set a franchise record by winning 12 games in 2002, cruising to the postseason with ease.


They were never seriously challenged in the playoffs, trouncing the 49ers and Eagles by a combined 42 points. For the first time in franchise history, the Buccaneers were in the Super Bowl.


In a dramatic twist, Gruden faced his old team, the Raiders, in Super Bowl XXXVII. Despite plenty of buildup, it wasn’t much of a contest, as the Buccaneers opened up a 20-3 lead by halftime and cruised to a 48-21 victory, sealing it with a pair of pick-sixes in the last two minutes.

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Gruden spent six more seasons in Tampa, but he never won another playoff game. The Buccaneers were hurt by high-profile disputes with some of their biggest stars, including Warren Sapp and Keyshawn Johnson.

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Al Messerschmidt/Getty

Source: ESPN


The Buccaneers also suffered from poor quarterback play, starting names like Chris Simms, Bruce Gradkowski, and a washed-up Jeff Garcia. None of Gruden’s passers in Tampa ever performed as well as Gannon.

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Matt Stroshane/Getty

After another playoff appearance in 2007, Gruden remarked that “the future is so bright around here I have to wear shades.” One year later, he was fired after coaching the team to a four-game losing streak to end the season.

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Matt Stroshane/Getty

Gruden could have found another coaching job, but he decided to try his hand at another line of work. In 2009, he was hired to replace Tony Kornheiser as an analyst on ESPN’s “Monday Night Football.”


Home viewers fell in love with his enthusiasm for the game and hilarious football jargon. He’s been known to employ phrases like “Spider 2 Y Banana” and “turkey hole” during broadcasts.

Source: NESN


All the while, he has maintained his trademark obsessiveness. Gruden often rises before 4 a.m., sometimes doing research and watching film at his desk for 12 hours or more.

Source: Bleacher Report


In 2015, James Miller reported that Gruden is the highest-paid employee at ESPN, raking in around $6.5 million a year.

Source: Twitter


Although he is popular in his current role, rumors that Gruden may return to the sideline seem to circulate every season. He recently stated that he would not rule out another coaching gig.

Read more: Jon Gruden says he may return to coaching, and 2 teams appear to be the most likely destinations


Currently, the University of Tennessee and the Buccaneers seem to be the most logical destinations, but he has also been linked to openings with teams like USC, Ohio State, and the Cleveland Browns over the years.

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Winslow Townson/Getty

Either way, there’s not a wrong choice. A return to coaching could be huge for the NFL, but Gruden seems to be more than happy sharing his love of football with the fans at home.


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