Jerry Jones and the Dallas Cowboys talk a big game every summer, annually proclaiming that they're all in on ending a Super Bowl drought that is quickly creeping up on thirty years. In fact, the last time the Dallas Cowboys won, or even made an appearance in the big game, it was Super Bowl XXX and Dallas was capping off a three-titles-in-four-years-run, which is a feat that has only since been accomplished by the New England Patriots (on two separate occasions).
At that point in time, Jerry Jones hadn't even owned the Dallas Cowboys for decade and he was already a three-time Super Bowl champion. Not a bad $140 million investment, especially considering that 35 years later, the Cowboys are the most expensive franchise in all of professional sports, now worth over $10 billion, according to Sportico. Yet you get the feeling that Jerry Jones' continued involvement with the franchise that he helped turn into America's Team in the 1990's is now holding the franchise back, because again, there's a near three-decade-long Super Bowl drought that is (rightfully) driving the folks in Big D crazy.
The argument here is that it's Jerry Jones' frugality and unwillingness to pull the trigger on long-term deals at the appropriate time that has held Dallas back. And given the current predicament the Cowboys find themselves in — where pending big-money, market-setting deals for Dak Prescott, CeeDee Lamb and Micah Parsons conflict with one another, when a savvier front office would've likely found a way to space these contracts out — it makes sense that ESPN's Mike Greenberg would launch an all out assault on Jerry Jones and his team.
“He bought the Dallas Cowboys in 1989 for $140 million, they’re now worth, as we saw yesterday, over $10 billion, which renders what I’m about to say hard to understand, but it is true… They are cheap. They are a cheap franchise,” Greenberg said during an appearance on The Pat McAfee Show. “Their cash spending every single season, look this up, text my boy Hembo and have him send you the numbers. Every year, their total cash outlay in players is the lowest in the NFL. It was the lowest last year, the lowest this year, and projects to be the lowest next year. They don’t spend money.”
Those numbers that Greeny referenced… they're nearly spot on. In 2024, the Cowboys are dead last in cash spending, according to Spotrac. They're projected to be dead last in 2025 as well. And in each of the last three years, they've been outside the top ten every season. Not really indicative of a team that is exhausting all options to contend for a Super Bowl.
Jerry Jones criticized for failed Cowboys contract negotiations
Greeny points out that it's not just that Jerry Jones is unwilling to pay his players… it's that he gets taken to the woodshed each time he negotiates with his top guys.
“Jerry gets into these poker games by trying not to spend money on players and he loses every single time,” Greenberg continued. “It goes all the way back to Emmitt Smith. He [Jones] got his clock cleaned in that negotiation. It goes back to him chasing Zeke Elliott down to Cabo, it goes back to the way he’s mishandled Dak, into Dak becoming, at some point soon, the richest football player to ever walk the face of planet Earth. He should have signed CeeDee Lamb a year ago this time, and he could’ve signed him for $25 million dollars a year, instead now he’s not going to get him for $35 million dollars a year. He mishandles these situations regularly.”
Cowboys legends like Emmitt Smith and Ezekiel Elliott, who have sat opposite of Jerry Jones at the negotiating table, have both spoken out on how poorly the Cowboys have mishandled contract negotiations with Dak Prescott and CeeDee Lamb. Despite their well-established lack of postseason success, Prescott and Lamb are the most prolific quarterback-wide receiver duo in team history, and if Jones squanders the chance to keep them together, it highlights that the 81-year-old's best days as the football decision maker of the world's most expensive sports franchise are behind him.
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