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As the 2019 NFL Draft approaches, much of the hype has, understandably, surrounded the star athletes hoping to get picked in the first round. But when the draft actually begins, a bigger spotlight will shine on the executives and coaches in charge of making those decisions. And there's probably no one under more scrutiny in that group than Oakland Raiders head coach Jon Gruden.

The Raiders are coming off a particularly disappointing 2018 season, and all of the confusion surrounding their scouting process makes their three first-round draft picks a must-watch. It's all a bit mystifying, and not at all what you'd expect from the highest-paid coach in the league.

Gruden took an unusual route to that contract, as a coach who won a Super Bowl ring but also took a decade away from coaching. Through his decades in football, he's amassed quite a fortune. How much is he worth?

Jon Gruden's Net Worth

Jon Gruden is estimated to be worth approximately $22.5 million for his NFL and broadcasting careers, at least according to Celebrity Net Worth. If this estimate is correct, it's a huge amount of money - though not as much as the estimated net worth of Patriots head coach Bill Belichick, which was estimated at $35 million.

Gruden also has quite a long way to go on his contract, so expect that number to grow.

Jon Gruden's Career

Gruden never had much of a shot at a playing career in football, stalling out as a back-up quarterback at the University of Dayton. But his coaching potential was seen immediately, and he was hired as a graduate assistant coach for the Volunteers at the University of Tennessee right out of college. He got his first taste of NFL coaching in 1990 as a special assistant coach for the Green Bay Packers, and after a short stint with the University of Pittsburgh in 1991 returned to the Packers for three years as a special assistant and wide receivers coach.

From there, Gruden got an even better chance to showcase his coaching prowess as the offensive coordinator for the Philadelphia Eagles. Working with quarterbacks like Randall Cunningham and Ty Detmer, Gruden impressed NFL executives enough that Al Davis, then the owner and general manager of the Oakland Raiders, hired him as their head coach for the 1998 season.

Jon Gruden and the Raiders

After two straight losing seasons, the Raiders hired Gruden. With the help of Gruden's coaching, as well as start first-round pick Charles Woodson, the Raiders improved in the 1998 season to 8-8, a record they would replicate in 1999. The team failed to make the playoffs both years, but made strides in these years, as well as an important acquisition: veteran quarterback Rich Gannon.

Gannon revived his career with Gruden as his coach, and in 2000 the team went from 8-8 to 12-4, winning the AFC West and making it all the way to the AFC Championship Game. An injury to Gannon in the previous game, however, kept him out of the Championship Game, and the team fell to the Ravens 16-3 to miss the Super Bowl.

Gruden's 2001 Raiders made the playoffs once again with a 10-6 record, making it to the Divisional Round of the playoffs. This, however, was the infamous "Tuck Rule" game against Tom Brady and the Patriots, where a controversial late-game call helped New England pull off a massive upset.

Jon Gruden with the Buccaneers

The 2001 playoffs ended in devastating fashion for the Raiders, but at this point Gruden was commonly seen in the NFL as one of its brightest young offensive minds. One team that noticed this was the Tampa Bay Buccaneers, who fired head coach Tony Dungy after multiple years of early exits in the playoffs and stalled offenses. The Bucs sought to replace Dungy with Gruden, and ended up making a massive trade with Oakland to get him, giving up two first-round picks, two second-round picks and cash to make Gruden the new head coach.

The Bucs offense improved somewhat in Gruden's first year, but it was their incredible defense that led them to a 12-4 record. Gruden's Tampa Bay team coasted to the Super Bowl, the first in the franchise's history, where they would play Gruden's former team, the Raiders, led by NFL MVP Rich Gannon, also got over the hump to make the Super Bowl. But Gruden's particular familiarity with Gannon and the Raiders made for the perfect gameplan; the Bucs defense dismantled the Gannon/Raiders offense, and Gruden came away with a 48-21 victory and a Super Bowl ring.

Gruden was a champion, but the Buccaneers suffered a brutal Super Bowl hangover, missing the playoffs in 2003 with a 7-9 record and then falling to 5-11 the year after. The 2005 Bucs, led by running back Cadillac Williams, rebounded with an 11-5 record but failed to win a playoff game. This was followed by a 4-12 season, and after missing the playoffs in three of four years, Gruden found himself on the hot seat.

2007 perhaps saved Gruden's job, as the team acquired veteran quarterback Jeff Garcia, and the improved offense led them to a 9-7 record and the NFC South title. The celebration was short lived, however, as they quickly fell to the eventual Super Bowl champion - the New York Giants. And after a brutal collapse at the end of the 2008 season saw Tampa fail to make the playoffs, the Bucaneers fired Gruden in January of 2009.

Jon Gruden's Broadcasting Career

Though Gruden's tenure with Tampa Bay ended in disappointing fashion, a Super Bowl championship and a decade of head coaching in the NFL made him one of the more recognizable faces in the game. Not long after his firing, ESPN announced that they would be hiring Gruden as an analyst for their Monday Night Football institution. Quickly, Gruden and his football analysis became synonymous with ESPN, and they made him a focal point of more of their football coverage. This included extended NFL Draft analysis and actual interviews with Gruden and college prospects in "Jon Gruden's QB Camp."

In 2014, ESPN signed Gruden to a contract extension to keep him with the network through 2021. Later, it was reported that Gruden could have been making $6.5 million a year with ESPN, the most of any of their on-air personalities. Still, much of Gruden's ESPN tenure included rumors and rumblings that he would one day return to head coaching.

Return to the Raiders

In 2018, one such rumbling finally came true. The Raiders announced in January of that year that Gruden would be returning to the team that traded him all those years ago, but this time for much more money. In replacing the fired Jack Del Rio, Gruden received a 10-year contract with Oakland worth $100 million, easily the largest for a head coach in NFL history.

His first season with the Raiders was rocky, to say the least. It started before the season even began when he traded star defensive player Khalil Mack to the Chicago Bears, and ended with a 4-12 record, as they would be the first team in the AFC to be eliminated from playoff contention. The lone bright spot of the season? The first-round draft picks Gruden acquired through trades to help build the future of the team.

Jon Gruden's Contract: How Much Does He Have Left?

As of this writing, Gruden has only coached through the first year of his record contract, meaning there are still nine years left to go on it. Gruden's draft picks will likely give NFL fans a better vision of what Gruden's plan is for those nine years.

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