Jon Gruden made his point, and all it cost was the final two years of Raider football in Oakland.
In the short term, anyway. The damage may be far worse down the road.
His decision to reportedly trade defensive stalwart Khalil Mack at the height of his powers to the Chicago Bears for a return of two first-round draft choices made it clear that his philosophies about roster construction and salary cap distribution are pre-eminent and do not include dissent or compromise. Mack was his best defensive player, perhaps his best player period, and yet Gruden made a minimal effort to engage with him, let alone negotiate.
This was my-way-or-the-highway brinksmanship by Gruden, who old-schooled the hell out of this seemingly simple problem by being the general manager of 1980 rather than 2020. He made this team worse, and probably next year's as well, all to prove a point that was never actually being challenged – he intends to operate as an autocrat, along the lines of the autocrat he himself couldn't get along with back in the day, Al Davis.
That comparison probably will stick in Gruden's craw some day, but for now he acted exactly as Davis would in his worst times. Mack was the most important of Raiders, and the only thing he insisted upon in return was to be paid commensurate with both his peers and his contemporaries in the sport.
And Gruden regarded it as a problem that had only one solution. His. He will suffer both in the short term and the long view for that belief.
Oh, it works well enough for Bill Belichick, but Gruden is not Belichick. Nobody is, and when Belichick retires having earned the right to be the last of the Paul Brown autocrats, nobody will be again.
And even if all this was a salary cap conundrum and Gruden's objection to Mack was simply a reluctance to have two $20 million players on the roster, his apparent inability/unwillingness to engage in a search for common ground is what will damn him in the long run.
It may also be a sign that he regards this Raider team as a structure to be torn down to the studs and rebuilt completely in his image, and that Mack for all his skill represents something he regards as a symbol for what the Raiders were under the old regime. This might be the Gruden rebuild we have all expected, only with a supporting wall as the first target.
The answer to that postulate is years away, and Gruden has the 10-year contract and $100 million price tag that allows this level of power-wielding. Owner Mark Davis would have been wrong to overrule him -- after all, a coaching search eight days before the season opener is an incredibly bad idea, because Gruden surely would have quit on principle. He could have afforded to quit, and even if he hadn't, he would have made Davis' life as hellish as he had his father's (and vice versa). It would not have been a fair fight.
But being a sports executive in the second decade of the 21st century requires a creativity than Gruden didn't seem to want to bother with, and his infatuation with the good old days of football includes an infatuation with the autocrats of the era. He fights against the tide of history, and the message he sent by trading Mack is being received by players both currently within the team's employ and those he may someday want to obtain.
In short, the whole Gruden 2.0 plan looks less likely to succeed in the long run than it did the day he was hired, because whatever gifts he has a coach do not apparently extend to the executive wing. The Mack deal needed to get done, or fail despite everyone's best efforts. There were no best efforts here, and the fault is principally Gruden's because the message of inflexibility rebounds back on its wielder, and brittleness only ends in shards. General managers and coaches who cannot bend get bent because the general managers and coaches of 40 years ago that Gruden admires so are the past.
There is, of course, the possibility that Gruden could end up being correct in this instance. Maybe Mack's game doesn't translate as seamlessly in Chicago, or maybe he gets hurt, or maybe the Bears will be the Bears. The future decides what it decides, and Gruden may indeed be smarter than everyone else in football on this one. For all we know, there may be a parade on The Strip in 2023 because Gruden decided to blow up this team and start again with players of his choosing.
But even if Gruden ends up on the right side of the issue, and trading Mack helps the team in the long run, the long run is Las Vegas' to enjoy rather than Oakland's. The Raiders leave in two years, and all the fan base will have gotten for these last 25 years is one lost Super Bowl, four playoff appearances and two of their most iconic figures revealing themselves as stubborn autocrats living on the fading charms of their pasts.
And in the end, the trade of Khalil Mack will end up being one more harsh reminder to Bay Area Raider fans that the future is not theirs but Nevada's. Oakland loses here, but so do the Raiders, and ultimately, there is an excellent chance that Jon Gruden lost too. His endless search for the good old days may very well end up getting him lost in a world that has moved on without him.