Will the Cowboys Win Another Super Bowl With Jerry Jones?

By | March 1, 2021

Love them or hate them, the Dallas Cowboys are America’s Team. Well, at least they were America’s Team.

Despite the Cowboys’ last Super Bowl appearance coming over 25 years ago, the team has one of the most loyal fanbases in sports. The team’s die-hard fans are scattered across the United States and the globe.

However, the dry spell begs one fundamental question. Will the Cowboys win another Super Bowl with Jerry Jones at the helm?

Jerry Jones Owner/GM/Super Fan

When Jerry Jones bought the Dallas Cowboys in 1989, he would forever change the NFL. Though nobody could have ever imagined the impacts Jones would have on the league, it was clear that the wildcat oilman from Arkansas wasn’t opposed to shaking things up.

It was the most considerable gamble of Jones’ life when he bought America’s Team for $140 million. The newest NFL owner had spent every penny he had on the franchise.

He immediately emphasized winning and unceremoniously fired the longtime and only head coach the Cowboys had ever had, Tom Landry. Jones became the villain in the eyes of NFL fans and Cowboy loyalists.

However, one thing in sports cures all. Winning will quickly turn even the most vilified into a hero in the eyes of fans.

Jones quickly named himself General Manager. The lifelong Dallas Cowboy fan now sits on the throne as the leader of all personnel decisions.

Now, it’s not uncommon for wealthy businesspeople to purchase their favorite sports team. However, it’s rare to this day for these new owners to appoint themselves a position that closely involves the product on the field.

Sure, the owner is writing the checks and needs to have some say, but not many of them crowd into the war room on draft day and mold the team’s future.

This has been Jerry Jones’s “MO” since he came into the league, and the owner/GM/fan has had a fair share of hits and misses. Let’s start by examining his early success and how it’s molded an opposition to change.

Building a Dynasty

Jerry Jones knew that the modern game had surpassed the legendary Tom Landry. Still, the firing seemed very personal.

Almost like Jones came into the NFL and needed to make the statement that was now his team. He didn’t want a franchise treasure blocking any of his shine.

So, Jones brought in the outstanding coach and better human Jimmy Johnson. Jones’ willingness to win at any cost paired with Johnson’s brilliant view of the game appeared to be a match made in heaven. 

That first season was challenging, to say the least. The Cowboys went an abysmal 1-15, and eyes were rolling across the NFL. Jerry Jones had fired Landry and barely managed to win a single game.

However, Jimmy Johnson has an exceptional talent for spotting and acquiring talent. The team’s and one of the largest trades in NFL history involved the team moving star running back to the Minnesota Vikings for a ton of premium draft picks.

Dallas Cowboys

The Cowboys quickly added stars and future Hall of Famers Troy Aikman and Emmitt Smith to join the third future Hall of Fame star, Michael Irvin. These three would go on to become “The Triplets.”

Johnson also brought in the tight end Jay Novacek, and the offensive threat was as formidable as any in the NFL.

In 1990, Johnson had led the team to a much improved 7-9. This impressive feat earned Johnson Coach of the Year honors.

By 1992, the Cowboys were back to the Super Bowl and facing off against the Buffalo Bills. This would be the team’s first Lombardi trophy since 1977 and the first of back to back titles.

Unfortunately, 1993 had the same results in store for the Bills. They lost what wasn’t a very close game to the Cowboys.

Five years into Jones’s reign as owner and GM, the Cowboys had won consecutive Super Bowls and showed no signs of slowing down.

However, change was coming, and it was not a change for the better. There’s no telling how many Super Bowls the Cowboys may have won with Jimmy Johnson and Troy Aikman, but Brady and Belichick come to mind.

Trouble in Paradise

Not many people would be surprised to hear that Jones has put his foot in his mouth. Jerry Jones is fun to watch because you never know what he may say.

Back in 1993, that wasn’t exactly the case. Or at least we hadn’t become as accustomed to it. 

Jerry Jones felt that Jimmy Johnson had slighted the owner during a victory toast following Super Bowl XXVIII. This slight apparently infuriated the owner/GM, and one night Jones found himself angry enough and drunk enough to gush to a bar full of sportswriters.

Jones allegedly stated that 500 coaches would have won a Super Bowl with this team.

Jimmy Johnson, as you may have guessed, didn’t appreciate Jones’ comments. Johnson had plenty of reason to be angry.

Jimmy had built the formidable teams. Johnson had a hand in all of it, from the players on the field to the game’s best assistant and position coaches.

So, he did what most people wish they had the constitution to do. He walked away.

If it’s so easy to win with the team that Johnson built, Jones shouldn’t have any issues finding the next Super Bowl-winning coach.

For the most part, Jones’ and the Cowboys hardly skipped a beat. The hotshot head coach of the Oklahoma Sooners, Barry Switzer, made the short drive down I-35 to Dallas.

Switzer spent a year getting acclimated to the NFL and lost in the NFC title game. However, by 1995 the Cowboys were once again the reigning Super Bowl champions.

Switzer and Jones soon had their brand of issues and would part ways. Thus, they were leaving a void spanning over a quarter of a century without a return to the Super Bowl.

Discipline Issues

The Cowboys have faced several issues over the past two decades. One that looms the largest in the minds of most comes down to a single word; discipline.

Since Jerry Jones took ownership of the Dallas Cowboys, the team has had several players struggle with problems away from the game.

These go back to the 1990s with stars like Michael Irvin and the now-infamous White House. More recently, the team endured heartbreak and loss when teammate Jerry Brown Jr. lost his life in a DUI accident.

Brown’s friend and fellow Cowboy Josh Brent was behind the wheel in the fatal crash. Unbelievably, and inexcusably, Josh Brent was on the sidelines only a few days after the incident.

Brent then served his NFL suspension and fulfilled his criminal obligations to be back with the Cowboys in 2014. This theme of being given immeasurable latitude off the field as long as the field effort helps a winning season is a recurring one.

Cowboys Stadium

Still, it’s not just the discipline issues off the field that I’m referring to regarding the lack of leadership.

The Dallas Cowboys have been among the worst in the league for penalties over the last 20 years. They always seem to have an unforced error at the most inopportune time.

The defense seems only to want to tackle the ball carrier if the offense is pulling their weight; it’s a mess year in and year out.

All of this adds up to 2 decades of mediocrity. Furthermore, it’s the result of a tremendous lack of leadership. Players know that they have only one boss in the organization, and his name is Jerry.

As long as daddy, a.k.a. Jerry Jones, is happy with you, it matters little what the coaching staff has to say.

A Tarnished Legacy

Don’t get me wrong; Jerry Jones has done tremendous things for the Dallas Cowboys and the NFL. The lucrative TV contracts, expansion, and billion-plus dollar stadiums are mostly thanks to the Cowboys’ owner.

It was this effort plus the three Super Bowls that earned Jones an invitation to Canton, OH. In 2017, Jerry Jones was enshrined into the pro football hall of fame.

Regardless, suppose Jerry doesn’t bring another Lombardi Trophy home to Dallas while he’s still running the show. In that case, it will be a failure in the eyes of many.

Jimmy Johnson built the Super Bowl teams. The players he saw talent in and the coaches he put in place were all him.

The fact is that if he had stayed in Dallas, they could have easily won 4 or more in a row. It was perhaps the early success Jones had in the NFL that will ultimately be his biggest downfall.

Winning in the NFL is extremely difficult, and breezing into three Super Bowls may have given Jerry the impression that he’s a better “football man” than he genuinely is.


Will the Cowboys win another Super Bowl with Jerry Jones at the helm?

Anything is possible. Despite the team having all the world’s talent, it’s a no for now if they can’t become disciplined at their craft. I would love to see the storied franchise return to its former glory, but it seems one man is standing in their way.

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