How Is Jon Gruden’s $100 Million Contract Working Out, Raiders?

Jon Gruden’s return to the Oakland Raiders has been equal parts memorable and mediocre. This veteran NFL coach isn’t afraid to make big moves, but he’s struggled to put together a winning team. Standing at 4-4 in his second season back, people are beginning to wonder about the 10-year Raiders contract he signed before last season. 

At $100 million, Gruden is one of the highest-paid NFL coaches, but he hasn’t proved to have the magic he was believed to have as a young up-and-comer during his first go-around with the Oakland Raiders. 

Jon Gruden’s NFL career

The 56-year-old’s coaching career has become something of a legend. In 1998, Gruden took over for the Raiders at 35 years old. After two straight 8-8 seasons, he transformed Oakland into a playoff team for the first time since they moved back from Los Angeles.

Despite two straight postseason berths, however, the team traded Gruden to the Tampa Bay Buccaneers in 2002. There, he got almost immediate satisfaction by beating his former team in the Super Bowl. His tenure afterward, however, was largely disappointing save for an 11-5 season in 2005.

In 2008, Gruden gave up coaching and became a mainstay on NFL broadcasts. People liked his insights, but the Sandusky, Ohio native was consistently floated as a candidate for NFL coaching jobs.

With Gruden’s cushy ESPN job, many believed his coaching days were behind him. Then, the Raiders came calling to the tune of $100 million, giving Gruden an offer he could not refuse. 

Gruden’s $100 million contract

The $100 million deal Gruden signed has been disputed, but no other amount has ever been reported. The 10 years it entails are a huge commitment for someone who hasn’t coached in over a decade and whose resume is marred with inconsistency. The deal is reportedly heavily backloaded, with Gruden earning $25 million during the first half and $75 million on the back end.

With the team headed to Las Vegas, they swung for the fences and brought in a respected coach who is recognized around the league. Almost immediately, people questioned whether anyone was worth this kind of money and commitment, even if they did win a Super Bowl 16 years prior.

NFL teams are allowed to pay coaches what they want. Although the details of New England Coach Bill Belichick’s contract are not public, it’s believed he makes more on a year-to-year basis. Belichick, however, became the Patriots’ coach around the same time and has put them in contention ever since. 

Gruden held a 95-85 record when he first took over — a respectable, albeit uninspiring number. He’s lauded for an impressive five-year run leading up to his Super Bowl victory, but Gruden’s run afterward only included two playoff games and a lot of mediocre seasons. To offer 10 years to this kind of coach is a risk, but did it pay off?

Gruden’s return to the Raiders

A lot has been made about Gruden’s return to the Raiders since the contract was finalized in 2018. Some saw it as a brilliant move, while others believed it overpays for someone whose career is largely based on myth.

Gruden, who many believe is acting as the de facto general manager, has made big moves by letting go of superstar Khalil Mack after his holdout and bringing in Antonio Brown. Unfortunately, neither proved fruitful. 

At 4-4 heading into the ninth game of the 2019 season, the Raiders must expect more than .500 football entering the latter half of the season. While it’s early in his contract, it’s not too early to worry about it. Gruden has said he would not stay 10 years if he didn’t think he was helping the team. If he is a man of his word, his time to step down could come soon.