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Jon Gruden’s 10-Year Plan for Total Domination

The Oakland Raiders fired general manager Reggie McKenzie on Monday, the latest step in the overhaul of the franchise under Gruden.  He’s accumulated much in the way of decision-making power, money, job security, and draft picks—will he wield it wisely?

John Gruden and Reggie McKenzie Getty Images/Ringer illustration

There are about 3,320 days left on Jon Gruden’s contract. With the rate the sport is changing, it is hard to say for certain what anything will look like in a few years, let alone which schemes will be en vogue, or what kind of quarterback will be the prototype. When Sean McVay’s current contract expires, Gruden’s will have six years remaining. The longest player contract in the NFL runs through 2024, an honor shared by Khalil Mack, Aaron Donald, and Zack Martin. We know almost nothing about football in 10 years. The Wikipedia page for the year 2028 is nearly empty. Very little is known about what will happen then in sports or otherwise, except that Jon Gruden will be either coaching or getting paid not to.

One of the remarkable things about Gruden’s unpredictable 11-month tenure is that it is not yet in its final form. The Raiders have not gone full Gruden. But that’s coming. Gruden hasn’t hired many of his own people yet and he’s been working with a general manager he didn’t hand-pick. Many of his players aren’t his. His tenure so far seems very Gruden and it’s going to get even more so. That process started with Monday’s news that Reggie McKenzie, the team’s general manager for the last seven years, has been fired. McKenzie did not have a lot of power, which is to be expected when your coworker gets a 10-year, $100 million contract, as CBS Sports’ Will Brinson pointed out. But he certainly had a role to play in the organization. According to The Athletic’s Vic Tafur, one of the reasons McKenzie was fired was because he didn’t get enough in return when the Raiders traded Mack to the Bears for first-round picks in 2019 and 2020, a third-round in 2020, and a sixth-round pick in 2019, a trade he was against. Tafur reported that the Bears “forced McKenzie to give back a 2020 second-rounder when they realized the Raiders were desperate to make a move.”

McKenzie wasn’t perfect. His last three draft classes were subpar, but it wasn’t his idea to trade the star players he did draft. After the Raiders dealt Mack, they traded receiver Amari Cooper, the no. 4 pick in 2015, to the Cowboys for a 2019 first-rounder. Punishing McKenzie for failing to maximize the Mack trade is like asking someone to take a torch to a house without any direction and then getting angry that they burned the wrong rooms.

Robert Caro, the author who has spent his career studying people in power, said that along with the cliche that power always corrupts, it’s equally true that “power always reveals.” We haven’t actually seen Gruden in his truest form. We will now. He has, via owner Mark Davis, been given what amounts to unlimited power in the organization for the next nine years, for better or worse. Gruden’s press conference Monday following the news of McKenzie’s firing was, honestly, quite funny. Gruden said he didn’t know the firing was coming, though as The Athletic’s Tim Kawakami points out: “that’s a bit of misdirection. This team is Gruden now. All Gruden.” “All Gruden” means many things, and that includes Gruden saying he hopes the new GM can be convinced to re-sign tight end Jared Cook. It means Bruce Allen and Mark Dominik, former coworkers of Gruden’s, are reportedly candidates for a new front-office role. “All Gruden” involves saying he and McKenzie were “very connected” despite the fact that Gruden is the most powerful person in the organization that just fired McKenzie. “All Gruden” means there are 3,000 more days of this.

The decisions Gruden has made have rewritten the 2018 season in a way Raiders fans won’t like. The Bears, with Mack in the fold, will not only win the NFC North, but they look capable of winning a playoff game or two. Cooper’s impact cannot be overstated. It’s likely he saved Jason Garrett’s job, changed the course of the NFC, and turned Dak Prescott into a good quarterback for the first time since 2016. McKenzie will probably help a team next year as a front-office executive. He comes from a stable of former Green Bay Packers talent evaluators who have a lot of power in this league, and because of his connections to multiple teams, he won’t be out of work long if he doesn’t want to be.

McKenzie’s biggest service to Gruden is the cache of draft picks he’s left behind after trading away the Raiders’ star players. Gruden will have three first-round picks in 2019 and two in 2020, though the 2019 picks from Chicago and Dallas will likely be late in the first round because of how effective Mack and Cooper have been. What Gruden will do with those picks is up for debate. In September, the NFL Network reported a “divide” among Raiders scouts, split between Gruden and McKenzie loyalists, with Gruden’s side being led by a confidant who “rose to prominence as a voice on Twitter with controversial takes that included Von Miller will be a bust and Jake Locker should go No. 1 in the draft,” according to Ian Rapoport.

The Raiders’ first-round pick from this year’s draft, Kolton Miller, is the 75th-graded tackle in the NFL. He’s allowed the most hurries, the most sacks, and the second-most pressures among all tackles in the NFL. Any number of stars-in-waiting were picked just after him, including Derwin James, Jaire Alexander, and Leighton Vander Esch. Gruden said he wanted James but the team had spent too much draft capital on safeties in recent years—a not-so-veiled way of saying that McKenzie had missed on those picks.

The McKenzie era was not particularly successful overall, but his efforts building the 2016 roster are, in the context of the franchise, pretty heroic. The Raiders did not have a winning season from 2003 until 2016. The reason they did not win a playoff game in 2016 is that Derek Carr broke his leg late in the season. The team never recovered: Carr never regained his 2016 form, and a 6-10 season in 2017 led to the firing of Jack Del Rio and the stripping of power from McKenzie. The last person to take a bad Raiders team and make it good was … Gruden, who took over in 1998 after three non-winning seasons in a row. McKenzie did not build a perfect team, but he cleaned up salary cap problems and drafted some NFL stars. Firing McKenzie is not necessarily a bad move—some of his draft picks have been terrible—but giving Gruden unlimited powers is.

Gruden essentially has a blank slate. McKenzie structured quarterback Derek Carr’s contract so that if the team wanted to move on from him this offseason in favor of a cheaper option, it would cost less than $8 million in dead money. His cap number for 2019 is $22.5 million. The Raiders’ only real commitment is to Gruden. That deal struck last winter, in terms of years, money, and power, is a misunderstanding of football and a misunderstanding of Gruden, who only won double-digit games twice during his seven-year stint with the Tampa Bay Buccaneers, neither of which came in his final three seasons. The game has probably reinvented itself three or four times since 2008, which was the last time Gruden coached, and it is going to keep changing.

When Gruden left Tampa Bay in 2008 he was embroiled in various feuds with Jeff Garcia, Chris Simms, Simeon Rice, and Michael Clayton, among many others. His track record suggests that he probably wears on people and is not the type of person you want to build a 10-year plan around. We have no evidence yet whether he will adapt to the schematic times. His team is 29th in points this year, which is bad for an alleged offensive guru, but it’s not the worst of his career. In 2006, his Bucs were 31st. In fact, his teams have not ranked in the top half of scoring offenses since 2001 (his last stint with the Raiders).

The thing I keep coming back to with Gruden is that the game is evolving quicker than ever before. Ideas from the lower levels of football are more prevalent. The Bears scored against the Rams on Sunday night with a play they installed two days before kickoff. The next nine years will be defined by adaptability, innovation, and smart ideas. This is not to say Gruden has none of these—he will, by law of averages, have some successful seasons over the lifespan of a decade-long deal—but you can get a much better coach than Gruden for far less money and for far less years on a contract. There was no evidence that Gruden is equipped for this era, and after he traded away two stars who made their new teams dramatically better, that’s still true. Perhaps the rationale behind these moves is to build hype for the Raiders’ pending move to Las Vegas, which now looks like it might be done without any of the players who starred on the team in Oakland.

It may seem like criticizing Gruden is low-hanging fruit. His performance has been so subpar that ripping a Super Bowl winner, the highest-paid coach in the sport, and the person with the most job security is seen as punching down. But it’s not. He has full power now, and the organization is “All Gruden.” McKenzie won Executive of the Year in 2016. Gruden could win Executive of the Year in 2018 for his performance helping the Bears and Cowboys, but not the Raiders.