Jerry Jones' 7 Biggest Mistakes as Dallas Cowboys GM

Jerry Jones has turned the Dallas Cowboys into one of the NFL’s most lucrative franchises. It is also the most popular football team in the NFL. But despite the team’s off-the-field success, they have been unable to translate their popularity into a Super Bowl win.

Dallas has some of the league’s most talented players in quarterback Tony Romo, linebacker DeMarcus Ware, running back DeMarco Murray and nose tackle Jay Ratliff, just to name a few. Jones has not made many missteps during his time as owner and general manager, but the few that he has made have been magnified.

Let’s take a look at seven of the Cowboys' owner's largest errors.

Trading for Former Detroit Lions Wide Receiver Roy Williams

Back in 2008, the Cowboys traded for wide receiver Roy Williams. Jones gave up a first-, third- and sixth-round pick for Williams. He then signed a five-year extension worth $45 million with $20 million guaranteed.

Williams gave the Cowboys two-and-a-half years of service with 94 catches and 1,324 receiving yards.

Jones finally admitted his mistake and released Williams after the 2010 season. The issue with Williams was that he never lived up to his contract. His production was OK for a No. 2 guy, as he gave the Cowboys seven touchdowns in 2009 with almost 600 receiving yards.

It was the amount of money the Cowboys paid him that fans and the team could no longer stomach.

Jones' Failure to Sign Emmitt Smith in 1993

The Cowboys were coming off of a Super Bowl win from the previous season, and Emmitt Smith wanted more money. Jones told Smith that he was worth just $10 million over four years, and Smith went home to Florida.

When the Cowboys lost their first two games of the season in '93, Jones had a sudden change of heart and signed Smith to a four-year deal worth over $13.5 million.

The Cowboys went on to repeat as Super Bowl champions, as Smith came back to save the day.

Releasing Jimmy Johnson

This one probably should have been No. 1, but at least it's on the list. The way the story goes depends on which article you read. Either way, Johnson left the Cowboys following their second Super Bowl in 1993.

No one knows just how great Johnson would have been if he would have stayed; it is just sad that we never got to see just how far Johnson would have taken the Cowboys. It may have fell apart regardless of Johnson and Jones’ relationship. Egos were involved as well as drugs and money. Not really a good combination.

The Cowboys' train kept moving after Johnson’s departure, but Dallas is still searching for a coach who can bring the same amount of success as Johnson.

Hiring Wade Phillips

Wade Phillips has a great defensive mind. He's been a very good defensive coordinator as evidenced by his coaching tenure with several different teams.

He just shouldn't have been a head coach for any team, especially the Cowboys.

In his first season, he went 13-3 and took the Cowboys to the playoffs and saw them get bounced in the second round.

Phillips compiled a record of 34-22 in Dallas with one playoff win. To his credit, he did win the Cowboys' first playoff game since 1996.

Phillips is a nice guy who comes across as aloof and disengaged. Jones made a mistake by hiring him, and it never seemed that Wade had a hold on the Cowboys.

Trading for Joey Galloway

Jerry Jones said that he would have to flip a coin on which was worse for his beloved franchise. He spent two first-round picks on Galloway, and in return Galloway gave the Cowboys 12 touchdowns and 2,341 in 48 games.

Galloway cost Jones $42 million over seven years. So I think it's safe to say that he would want a re-do on this situation.  

Passing on Randy Moss

I struggle with this one because Jones wants to clean up the culture at Valley Ranch. Moss was labeled as trouble before the 1998 draft, and Jones had the opportunity to pick him. He passed on him and Moss made him pay.

Against the Cowboys, Moss compiled 607 receiving yards and 10 touchdowns.

Moss would have given Dallas great service, but at what cost? How many blow-ups? Locker-room problems? Maybe arrests? Not sure if it would have been worth the trouble, but Moss destroyed Dallas each and every time they faced off.

Jerry Jones' Super Bowl Error

The NFL rolled out the red carpet for the Super Bowl in 2011 in Dallas, Texas. The problem with that is the snow and dreary weather that came with it. The Steelers and Packers faced off, but media and fans complained of issues with concessions and security.

Then there was the problem with over 400 seats, and the NFL had to issue refunds to fans who paid upwards of $60,000 for their seats.

It did not go over smoothly, and Jones had a partial black eye because of it. I'm sure Dallas will be in play for another Super Bowl soon, but the one in 2011 was very underwhelming.