Jerry Jones Walks in Circles (1993)
The last hurrah of the NFL's emptiest showman.
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I.
Three decades ago, back when he was forging his reputation as a Barnumesque showman amid a staid cadre of billionaire professional football team owners, Jerry Jones made a huge mistake. His franchise, the Dallas Cowboys, had just won the Super Bowl, and Jones thought he could get away with lowballing his star running back, Emmitt Smith, when it came time to negotiate a new contract. Jones piled on a litany of flimsy excuses for his obstinance, most notably the impending salary cap in the NFL. He “waged a one-sided campaign in the local media,” wrote Fort Worth Star-Telegram columnist Gil LeBreton, “hoping to retain public favor.”
Jones held firm heading into the 1993 season, and so did Smith, who sat out the first two games and watched with a certain amount of glee as the Cowboys lost both of those games. Only then, after the Cowboys lost to the Buffalo Bills—the team they had defeated in the Super Bowl, and would defeat again in the next Super Bowl—did Jerry Jones give in. Only then did Jones offer Emmitt Smith the contract he actually deserved. And then, as a born huckster like Jones is wont to do, he attempted to save face by declaring the whole thing a draw.
“Somebody is going to ask me who won in these negotiations,” Jones told the media. “In my opinion, this is a win-win deal.”
II.
The other day, in the midst of yet another rambling attempt to justify his ongoing refusal to yet again pay one of his best players what he deserves—in this case, linebacker Micah Parsons—Jones cited the negotiations with Emmitt Smith, along with the protracted and often baffling contract disputes he’s had more recently with pretty much every standout player on his roster, as proof that something would get done eventually. He made some kind of musty reference to negotiating (or not negotiating, I’m not actually sure) with Jay-Z on a contract with former receiver Dez Bryant. He made more than one solemn declaration that a football player, upon signing a contract, could actually get hurt, and he seemed to believe that this was the kind of profound negotiating tactic that elevated him above the hoi-polloi and entitled him to retain his position as the general manager of the Dallas Cowboys.
Jones is 82 years old, and while I am believer that age should not be an automatic disqualifying factor when it comes to serving in positions of leadership, I also believe that one of the things that should factor in is the ability to accept and weather inevitable societal changes. Jerry Jones appears to have no interest in changing at all; he still often treats his own players with a disrespect that often borders on racism. (Even now, in 2025, he appears to deliberately address the Washington football team by a nickname that is widely regarded as a racist and abhorrent appellation conjured by a racist and abhorrent former NFL owner.)
Jones not only hasn’t changed at all over the course of 30 years—he seems to have no interest in changing, which is why he blithely and unironically likens the huge mistake he made with Emmitt Smith 30 years ago to the huge mistake he’s making right now. Jones views himself as a riverboat gambler who treats negotiating as a zero-sum game in itself, without realizing how it might affect his team’s ability to actually win games. (This is, after all, a guy who made his way through college by selling flimsy and poorly made shoes to his classmates.) In the same way, Jones seems to care more about pumping up the value of his franchise by tapping into the attention economy than he does about his franchise actually succeeding. And that is how you wind up with a team that hasn’t made it back to the NFC Championship game in three decades.
The purpose of the Dallas Cowboys in 2025, as dictated by Jerry Jones, is simply to perpetuate the mythology of the Dallas Cowboys. And you can only get by that way for so long before people start to realize that you’re running them around in the same circles, over and over again.
III.
I can’t imagine there is anyone left outside of the Cowboys organization who believes that Jerry Jones is actually a force of good for the Dallas Cowboys. But it doesn’t matter; he is the sporting equivalent of an authoritarian who refuses to cede power.
Ten years ago, ESPN’s Don Van Natta Jr. spent time for Jones for an epic profile that revealed both his up-close charisma and his own central vulnerability: He desperately wants to be known as a smart football man. Except this is simply not the case; if it was, we would have seen it by now. Jerry Jones is not possessed of the brilliant football mind that Al Davis was in his prime, and he never will be. And yet Jones refuses to comes to term with his own limitations, just as Davis did later on in his career. And this is why, over the course of a generation, the Cowboys’ presence in the NFL has withered from strength to indifference.
“…more than any other owner in the NFL or any other sport, Jones loves being quoted and adores the spotlight,” Van Natta wrote. “A brilliant entrepreneur, genius brand builder, marketing wizard and Tasmanian devil of a pitchman who has sold shoes, insurance policies and oil and gas, Jones is a master promoter of his team, his stadium, the league and himself.”
I’m sure Jones loved reading that sentence in 2014. Hell, I’m sure he’d love reading it now. But a decade later, that sentence seems to have lost all of its punch. After a while, if you’re a riverboat gambler who can’t win anything, the whole posture curdles. You begin to look obstinate and pathetic. You become an old man who refused to learn any of the object lessons that life is supposed to teach you.
To watch Jerry Jones fade before our eyes is to realize that this era we’re living through—this era of sideshows and empty gestures—will someday be viewed with the same contempt. You can only fool the people for so long, and then they start to realize that you’re just trying to sell them the same cheap pair of shoes.
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Changing a few words here or there for context purposes, this newsletter could have easily been about our country's president instead of Jerry Jones. I also contend if you created a Vin diagram of Cowboy fans and MAGA supports, there would be a large portion of the represented between the two circles.