The glory of Jerry Jones’s three Super Bowl rings has been overshadowed by nearly three decades of postseason disappointment, raising concerns for the Dallas Cowboys‘ owner. Now at 83, the obvious question starts to surface: Shouldn’t Jerry retire? That question has only grown louder as Dallas once again enters an offseason defined by unmet expectations, with the pursuit of a sixth franchise Lombardi on hold for at least another year. His recent actions, however, suggest his definition of an endgame is far different from what most expect.

“I’m going to have to say this to everybody in this room: I don’t know what your ages are, but I hope — let’s just say [Stephen Jones’] age — if he has as much fun between where he is today and where I am today in age, if he has as much fun as the guy sitting here beside him, he’s in for a hell of a ride and a hell of a life,” Jones recently said. “I’ve had the most fun in the last 20, 21 years.”

Strip it down, and the message is simple. Jerry Jones has no plans to retire anytime soon. Nor does he appear interested in stepping away from his role as general manager while the Cowboys remain stuck outside the NFL’s true contender class. Even if the Cowboys have to wait at least one more year for that elusive sixth Lombardi as a franchise and a third Super Bowl win under his ownership, Jones sounds fully committed to seeing this through. He’s also very clear about what the finish line looks like for him.

“Everybody likes to dream, and I promise you high and hard on my dream list, way ahead of making a buck, because I don’t need a buck — way ahead of that is to go down as the owner that won the most Super Bowls.”

That context matters. The Cowboys last won it all in the 1995-96 season, and the drought since then only adds to the sense of unfinished business. Dallas has now gone 30 seasons without another championship, including a disappointing 7–9–1 finish this past year and consecutive playoff absences. Right now, only two franchises sit above Dallas in total Super Bowl titles. We’re talking about the Pittsburgh Steelers and the New England Patriots, both with six.

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The Steelers’ latest run ended early after a Wild Card loss to the Houston Texans. The Patriots, meanwhile, are still chasing a seventh with Drake Maye and new head coach Mike Vrabel. But when it comes to owners, the gap is even clearer. Robert Kraft sits at the top with six Super Bowl wins. Jerry has three. That’s the real challenge in front of him.

If Jerry wants to become the winningest owner in Super Bowl history, it won’t come from incremental tweaks. It would take building another full-blown dynasty, likely starting with major roster and coaching decisions in the 2026 offseason. Whether Jerry is ready to take that swing again at this stage is the real question.

Jerry Jones’ hunt for a new defensive coordinator continues

Ever since moving on from Matt Eberflus, Jerry Jones has been actively searching for the next defensive coordinator in Dallas. Eberflus’ dismissal marked the fourth change at defensive coordinator in as many seasons, underscoring how aggressively the organization has been trying, and failing, to stabilize that side of the ball. So far, Dallas has interviewed Daronté Jones, the Minnesota Vikings’ defensive pass game coordinator, Ephraim Banda from the Cleveland Browns, and Jim Leonhard, the Denver Broncos’ defensive pass game coordinator. But the list doesn’t stop here.

Three more names remain very much in the mix. That includes current Cowboys defensive line coach Aaron Whitecotton, who interviewed on Monday, along with the Baltimore Ravens‘ DC, Zachary Orr, and ex-Arizona Cardinals‘ head coach Jonathan Gannon, both of whom are expected to interview on Tuesday. And each of these candidates brings a different kind of appeal.

Whitecotton stands out immediately because he’s the only internal option Dallas has interviewed. While the 2025 season was his first with the Cowboys, he brings built-in familiarity. Before arriving in Dallas, Whitecotton spent four seasons as the Jets’ defensive line coach, working closely with Quinnen Williams for most of that stretch. Jones has already pointed to Williams, along with Kenny Clark and Osa Odighizuwa, as the current foundation of the defensive front, making continuity up front a notable factor in Whitecotton’s candidacy.

Gannon, meanwhile, fits a familiar Cowboys pattern. Dallas has hired former NFL head coaches as defensive coordinators in each of its last five DC hires. Gannon went 15–36 over three seasons as the Cardinals’ head coach, but his résumé as a coordinator carries more weight. During his time with the Eagles, Philadelphia’s defense finished inside the top 16 in both 2021 and 2022, earning him league-wide respect.

Then there’s Orr. He spent four years as a defensive assistant under John Harbaugh in Baltimore, had a brief stop in Jacksonville, and returned to the Ravens in 2022 as inside linebackers coach before earning a promotion to DC. His rise has been steady, and his system familiarity makes him a serious contender.

Bottom line: all three candidates check boxes, either through internal familiarity, head coaching experience, or developmental credibility. With the defense coming off a franchise-record 511 points allowed and personnel questions looming at multiple levels, this hire represents more than just another staff change; it’s a signal of how urgently Jerry Jones believes the Cowboys can still close the gap.

Whether Jones leans toward one of these names or pivots elsewhere will say a lot about how aggressive he plans to be in his quest to win more Super Bowls than any owner.