Complex legacy of Cowboys owner Jones could use a positive turn

Long-time Dallas Cowboys owner Jerry Jones is in the conversation for most unique characters to ever grace the National Football League. And he's certainly amongst the most influential in pro football history.

An ever-present figure at the massive AT&T Stadium in Arlington, Texas, - the so-called 'House that Jerry Built' - Jones' comfortability in the spotlight and notoriety in the league is unmatched in the modern age.

But the colourful character's legacy now can perhaps best be described using the title of Sergio Leone's 1966 Western thriller: The Good, The Bad, and the Ugly.

The Good - Jerry Jones builds America's Team

Jones bought the Cowboys in 1989 for a paltry $140 million and transformed the team into the most profitable sports franchise in the United States, with a value surpassing $10 billion in 2024, per Forbes.

The oil magnate and businessman was also instrumental in the growth of the NFL, and as a member of the NFL's board of governors in the 1990s, he helped the league start its path towards broadcasting mega-deals by enlisting Fox as a broadcaster through a bidding war over CBS.

Just months after Jones acquired the team, he cleaned house, firing franchise cornerstones and Pro Football Hall of Famers in head coach Tom Landry and general manager Tex Schramm.

Jones took over the general manager role, while adding Jimmy Johnson as head coach, and the success soon followed.

The Cowboys won three Super Bowls over the next seven seasons, with iconic stars such as Emmett Smith and Troy Aikman leading way.

Smith, the NFL's all-time leading rusher and a member of all three Super Bowl-winning Cowboys teams, thanked Jones personally in his Hall of Fame enshrinement speech.

"Jerry, thank you for believing in me as a football player and knowing that I can get the job done," Smith said.

The Bad - The Dallas Cowboys' prolonged era of mediocrity

The Cowboys have struggled mightily since that 27-17 victory over the Pittsburgh Steelers in Super Bowl XXX.

The team has won only five playoff games in the 30 years since and have failed to advance to a conference championship game.

Since the 2000 season, the Cowboys have a record of 4-10 in the postseason - the fourth-lowest winning percentage of any team in the NFL over that span. Only five teams have fewer playoff wins this century than the Cowboys' four.

The Cowboys have claimed seven division titles over the last 17 seasons, and have won only three of those seven home playoff games in that span.

The longest-tenured head coach under Jones' watch, Jason Garrett, especially encapsulated the struggles of the team in the post-Johnson era. Garrett led the team to more 8-8 seasons (four) than playoff appearances (three) in his nine years at the helm.

This with at least five players selected to the Pro Bowl every season from 2013-23, many times a league high.

Star players have long been attracted to playing in the biggest market with America's Team, but some of their inability to capture past glory may be attributed to the third component of Jones' fading legacy.

The Ugly - Jerry Jones, the negotiator

A recurring theme in Jones' ownership of the Cowboys has been his take-it-or-leave-it style of negotiating.

It started with the abrupt firing of two faces of the franchise, and has continued to devolve into chaos in recent years.

Contract disputes with star players spilling into the public have become a problem with the Cowboys in recent years, including quarterback Dak Prescott and wide receiver CeeDee Lamb before the 2024 season and offensive lineman Zack Martin before the two of them.

"Yeah, I mean, I stopped, honestly, listening to things (Jones) says to the media a long time ago," Prescott said eventually before signing a four-year deal worth $240 million in August of 2024. "It doesn't really hold weight with me."

Lamb staged a holdout in camp before last season, and when Jones made comments to the media regarding their contract negotiations, Lamb responded on social media with a post that simply said "lol."

And the situation is now playing out again ahead of the 2025 season, with superstar defensive lineman Micah Parsons still not with the team as he seeks an extension entering the final year of his rookie deal.

Parsons told reporters earlier in August that his "mouth was closed," regarding contract negotiations. Prescott offered support in the media for his teammate as the situation plays out.

“I can say from experience that it’s just frustrating,” Prescott said.  “I hate that he’s going through it, but as I’ve told him, keep handling things the way that you are, and I believe that he should be paid.”

What will Jerry Jones' legacy look like at the end of it all?

Jones was inducted into the Hall of Fame in 2017 as a builder, and it is impossible to discount his impact on the league and on the Cowboys.

At the same time, the team has been largely irrelevant since the turn of the 21st century. Only the Cleveland Browns, Miami Dolphins and Houston Texans have failed to make a conference championship game in the last 25 years.

There is one thing that cures all in the NFL though, and that is winning.

"I just want to say this: There's no substitute for winning," Jones said in 2019. "I know that's a cliché, but we must win. We will win. Win is the name of the game."