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Jon Gruden Has Ushered in a Golden Age of Dumb NFL Trades and We Cannot Thank Him Enough for It

Gruden was derided for trading away Khalil Mack, but he somehow managed to prise a first-round pick from the Dallas Cowboys for Amari Cooper. As Gruden knows all too well, it takes only one desperate partner to make a bad deal in the NFL.

Getty Images/Ringer illustration

Since his return to the NFL as head coach of the Oakland Raiders, Jon Gruden has been viewed as something of a leaguewide curiosity, a sentient meme with a haircut rather than a head coach. He has mostly brought this on himself with certain idiosyncratic tendencies. He wondered aloud at the NFL combine about the correct pronunciation of “data” (I mean really, who can be sure?) and he did little to alleviate concerns that his decade away from coaching would be a hindrance. He joked about wanting to throw the sport back to 1998 even as the game innovates every minute. As though aware of the perception among the football-viewing public that he is stubbornly set in his ways, Gruden punctuated a random point about playing rookies at a recent press conference with the question “What do you say to that, America?” addressed to no one in particular. And of course, he traded his best player, pass rusher Khalil Mack, before the start of the season only to then consistently lament the Raiders’ ineffective pass rush. The idea that there are at least nine more years of Gruden, as part of his 10-year, $100 million deal, makes all of these incidents gloomier. A website, Is Gruden Gone Yet?, counts down the seconds until Gruden’s contract expires and calculates how much money he’s earned since you clicked the link. It is perhaps the darkest part of the internet. Gruden is the closest example football has to John Mulaney’s joke about a horse loose in a hospital, in which the comedian attempts to sum up the current political climate by comparing it to a horse that’s loose in a hospital. Which is to say we don’t know exactly how this is going to go.

The most unpredictable act of Gruden’s tenure came on Monday, when he won a trade resoundingly. The Raiders sent Amari Cooper—who has averaged less than 50 yards a game since the start of the 2017 season—to Dallas for the Cowboys’ first-round pick, which, assuming they do not improve drastically, will be a fairly good one since the Cowboys are one of 14 teams currently under .500. Cooper’s yards per route run has declined three straight seasons and he hasn’t cracked the top 30 in his career in that metric. This season he’s 62nd among receivers. As it stands, Gruden will have three first-round picks in 2019 and $74 million in cap space. Like with the rest of Gruden’s tenure, we cannot rule out anything—he might package those picks for some veteran he fell in love with, perhaps to address that nagging pass rush issue. He might trade starting quarterback Derek Carr for some reason even though he said he won’t. It is not a perfect situation—the Raiders will not get a player as good as Mack with those assets—but having picks and cap space to move forward with is not a disaster. This is not going to be a Howie Roseman–style flawless rebuild, but it’s not a total loss. The Raiders are 1-5 and Carr does not look good, but all things considered Gruden could have easily steered the franchise toward being bad with no assets.

Raiders general manager Reggie McKenzie’s version of the story—that the Cowboys called, offered the pick, and “that’s what it came down to”—is miraculous only in that McKenzie did not hang up thinking it was a prank. This is the third time Cowboys owner Jerry Jones has traded at least one first for a receiver. He previously traded a boatload of picks, including a first, for Detroit’s Roy Williams, whose best season in Dallas led to a cool 596 yards. He also traded two firsts for Joey Galloway, whose high point with the Cowboys was 908 yards on a 5-11 Dallas team in 2002.

There’s an old joke that says when you are being chased by a bear, you don’t need to outrun the bear, just the person running alongside you. This is true in football. You do not need to be the smartest team in the league; you just have to find one team dumber than you and you’ll get value. Gruden found it Monday with the Cowboys. In September, it was the Raiders and Gruden whom the Chicago Bears found willing to part with an elite pass rusher.

Yahoo reported the Cowboys were essentially bidding against themselves at that price. In theory, Cooper is filling the void left by Dez Bryant, who was never truly replaced as the team’s top receiver. Bryant and Cooper were the only wide receivers last year to drop more than 13 percent of their passes. Carr has targeted Cooper just 32 times this season—possibly because Cooper does not camp out 1 yard from the line of scrimmage.

This bad trade will not be an outlier. The Raiders clearly wanted to dump Cooper—Jay Glazer reported as much last week, but he also thought they wouldn’t get a first-round pick and that they’d have to lower their asking price. Then came the Cowboys, a team that apparently did not care that Cooper is due for an extension as soon as this offseason. Cooper’s years as a value contract are over, as he’s set to make $13.9 million next year. There are not many ways to spin this as a good trade for the Cowboys. The more I look at the league, the more I think bad trades are the future. Glazer said over the weekend that the Oct. 30 trade deadline will be notably active. We could be entering into a golden era of dumb trades.


One of the beautifully chaotic things about the modernization of the NFL is that the league is not set up to be innovative. This is not just about trades, this is about every facet of the sport. As teams continue to adapt and evolve in a rapidly changing league, some will have no clue what to do. There are simply not enough visionaries running NFL teams to avoid having a much bigger group of “have nots” than “haves.” If you work at a technology company that wants to get into virtual reality, you hire people with an expertise in virtual reality to be in charge of it. In the NFL, they would simply take a 51-year-old guy named Doug and tell him to learn how to make virtual reality equipment. Sometimes this can work, oftentimes it does not. Take the latest offensive trend in the league: I talked to an offensive coordinator in the summer who said the college scheme revolution was, for now, going to have limited reach because so many NFL coaches were wildly unequipped to handle it. He told me he thought that the teams that could run RPOs well would do it and win, but more than anything, the bulk of the NFL would just run really bad RPOs because they think they should run RPOs. It’s the same process that led The Itchy & Scratchy Show to add Poochie the Dog—the idea that old people need to get hip without knowing how to do it.

Very few teams have devoted sufficient resources to their analytics departments, and the Los Angeles Chargers reportedly don’t even have one. The teams that have figured out all of these things—the Philadelphia Eagles, the Kansas City Chiefs, the Los Angeles Rams, the New England Patriots—have been rewarded. Other teams are struggling to catch up and the results are mixed. This extends to trades, where the notion of value is changing quickly because of the rookie wage scale. First-round picks are more valuable than they were a decade ago—and yet not everyone is on the same page. The salary cap rises $10 million a year, allowing teams to carry superstar salaries fairly easily. It is easier than ever to trade or acquire a big salary. At the same time, general managers have shown themselves to be more aggressive. This is going to lead to utter chaos.

It would be a neat narrative to say that there are two NFLs, but that’s not exactly what’s happening. You could say that the Cowboys do not understand value in the modern NFL, but you could also make the argument that the Raiders don’t either. It’s probably more accurate to say that with few exceptions, nobody knows anything right now. We have more data than at any point in the sport’s history, yet the vast majority of teams do not employ it effectively to improve their decision-making. Bill Belichick has been applying fairly basic economic principles to football for decades—trading back in the draft to acquire more picks and not acquiring overpriced players—and the Patriots are still considered an outlier among NFL teams.

The sport is constantly reinventing itself with new rules, new kinds of players, new schemes, and new data. The fact a team can lose the worst trade of the season and then win a massive trade weeks later is evidence that no one can keep up. The future of football is many things—Patrick Mahomes II, ruthless salary-cap management, and Sean McVay’s creative play-calling. It’s also dumb personnel moves executed in order to chase a game in which the rules change as soon as the majority of teams figure out how to operate within them. There are many more of them to come.