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Ten Years of Jon Gruden Is a Dream Come True—At Least for Mark Davis

On Tuesday, the Oakland Raiders announced that they officially signed Gruden to a baffling, record-breaking, decade-long deal to be the franchise’s head coach for a second time

An illustration of Jon Gruden in a Raiders visor with his hair colored highlighter yellow Getty Images/Ringer illustration

Here are some facts about Jon Gruden: He last held a head coaching job in the NFL in 2009. He rents an office in a Tampa strip mall where he compiles and reviews game tape. He on occasion convenes meetings of a group he calls the Fired Football Coaches Association. He is about to go from being ESPN’s highest-paid on-air personality to having more money guaranteed to him than any player currently in the NFL. He published a book titled Do You Love Football?!

On Tuesday, the Raiders formally anointed Gruden their head coach in a press conference with Raiders owner Mark Davis and GM Reggie McKenzie that saw Davis at one point stop to collect himself before thanking Gruden’s family “from the bottom of my heart for making my dream come true.” Gruden will reportedly receive a 10-year, $100 million contract, the longest and most expensive deal ever offered a coach and one that arrived in conjunction with the team’s apparent flouting of the Rooney Rule. (“I hope I’m a candidate,” he said last Tuesday, as reports swirled that he was already in the midst of hiring a staff.) Barring any construction delays, the Silver and Black will settle into their new home in a $1.9 billion, taxpayer-subsidized stadium outside Las Vegas in 2020, Year 3 of Gruden’s contract.

I encourage you to think more about the length and less about the number, eye-popping though it is. (“Ten million has always been the target,” NFL soothsayer Ian Rapoport said last week of previous attempts — the University of Tennessee, the Buccaneers, umpteen Grumored others — to lure Gruden back to coaching.) Because even as Davis finds new ways to stretch the boundaries of the word “overleveraged,” it’s the time frame that the team may come to feel most dearly. “I don’t have a guarantee to be alive for 10 years,” Gruden joked Tuesday.

The Raiders do not have a track record of keeping coaches around for long. In 2012, The Big Lead analyzed head-coaching tenure and team records across the league in an attempt to measure which teams were the most and least patient with coaches. The Raiders were the least-patient franchise by a wide margin. Gruden will mark the team’s third head coach since those numbers were analyzed. Now they will have Gruden — or else a pricey gap where an underwhelming Gruden used to be — for a decade, plus an assortment of hand-picked coordinators, among them Rams quarterbacks coach Greg Olson as offensive coordinator, Bengals DC Paul Guenther as defensive coordinator, and Cowboys special teams coach Rich Bisaccia as the coach for that group, reportedly offered four-year deals, unusually long for those positions. Davis, ever reluctant to pay out contracts, did so here, turning out his pockets to fulfill outgoing head coach Jack Del Rio’s four-year extension, signed just 10 months ago.

Gruden originally took charge of the Raiders in 1998; four years later, in the weeks after the Tuck Rule Game ended the Raiders’ 2001 season, he was dispatched of in a 1 a.m. phone call by the late Al Davis. To say that there’s lingering sentimentality toward Gruden on the part of Al’s son is an understatement: On Tuesday, he said that after his father’s death, his greatest hope was to bring Gruden back to the team. “It is the biggest day of my life right now,” he said.

But even Al, whose Raiders lost to Gruden’s Buccaneers in the Super Bowl the same year he traded the coach to Tampa Bay for a slew of draft picks — two first-rounders and two second-rounders, plus $8 million in cash — was keen to point to the coach’s fallibility. Months before the elder Davis’s death in 2011, he suggested that Gruden’s victory in the 2003 Super Bowl was the work of Gruden’s Tampa Bay’s predecessor, Tony Dungy. “[L]ook, Jon beat us in the goddamn Super Bowl, that’s the only thing I regret,” Davis told the San Jose Mercury News. “But take a look at Jon’s performance at Tampa.” Indeed, after his initial triumph, the results were decidedly mixed. Gruden spent seven seasons at the helm in Tampa; over the final three, his teams went 22–26.

It’s an interesting time to join the Raiders, who were one of the 2017 regular season’s great disappointments. After a 12–4 campaign in 2016 and a playoff run seemingly halted only by the Week 16 loss of quarterback Derek Carr, the Raiders were a not-exactly-dark-horse candidate for a deep run this winter. Instead, the team flailed, and then flailed some more, finishing 6–10. Was the dismal record in part the lingering result of Carr’s Week 4 back injury, after which he missed just one start but never seemed to fully regain his form? Was this a greater regression to the mean for Amari Cooper and Khalil Mack? Or was this the fault of Del Rio, brought in to lead the young team in 2015? Del Rio presided over the Carr-Cooper-Mack resurgence of the Raiders from perennial league bottom-feeders to serious contenders; he also had Carr, Cooper, Mack, and a dominant offensive line to help him. Both Mack and Carr, who signed a five-year, $125 million extension last year, will now have their fourth coach in just five years.

You can make the case, as Mark Davis did Tuesday, that overpaying for the right coach, a role that is not subject to a team’s salary cap, can make a lot of sense — that, essentially, a good coach is hard to find. A coach can even be worth a price as steep as the one the Buccaneers paid in 2002, given what followed the next year: “This is what people don’t understand,” former Bucs safety Dwight Smith, a member of the Tampa Bay championship team, told ESPN last month in a retrospective on the Gruden trade. “One Super Bowl is worth 20 years of mediocrity.” The trouble with Gruden, beyond his decade out of coaching, is that his record has often been less than inspiring. Are there enough good coaching moments to make, definitively, a good coach? Thanks to Davis, we’ll have plenty of time to find out.