There’s one thing holding the Dallas Cowboys organization back from being one of the best in the NFL: Jerry Jones. Without Jones, this team may have won a Super Bowl within the past 20 years. Many times, the ownership isn’t to blame when management is simply incompetent, but there’s no general manager to put blame on, because Jones never hired one. Jerry Jones likes to stay in control of everything dealing with the Cowboys organization, which is why he’s been holding on to the puppet of a head coach, Jason Garrett. Jones does a poor job of allowing his football operations staff to put together a team that can go out on Sundays and win. Rather than his staff putting the team together, Jones likes to put a lot of the team together himself.
A huge part of the poor drafting and free agent signings throughout Cowboy history have come under Jerry Jones' wing. However, lately Stephen Jones has taken over as the one to oversee who the Cowboys draft, which has led to some success. Jerry almost drafted Johnny Manziel back in 2014, but luckily, Stephen Jones managed to change that around for the Cowboys to select Zack Martin instead. Unfortunately, Cowboys fans have had to deal with generations of poor decision-making in the offseason.
16 Never Should've Drafted: Bruce Carter (LB)
The situation that the Cowboys faced with Bruce Carter, is in a way, very similar to the situation with Jaylon Smith. Carter was injured which is why he wasn’t selected in the first round, and he was expected to miss his rookie season, and then play in his sophomore year as a starter. Unlike Jaylon, Carter was able to play on special teams mid-way through his rookie year. Injuries kind of lingered throughout his career, which is why this pick became a mistake. Throughout three of the four seasons he played with the Cowboys, he was hurt. As it turned out, he would never start a full season in the NFL. Although there were sometimes he looked great, he could never stay healthy, which led him out of Dallas. Cowboys fans are hoping this won't happen to Smith.
15 Never Should've Signed: Eddie George (RB)
This signing wasn’t a game changing decision, but it was a decision that didn’t need to be made. At 31 years old, the Dallas Cowboys signed former Tennessee Titans running back Eddie George. Looking at it before the 2004 season, this looked like a pretty good deal – a one-year deal worth $1.5 million. Before coming to the Cowboys, George never had a season where he rushed for under 900 yards. He only failed to rush for under 1,000 yards once. George was like the Frank Gore of his generation in terms of his consistency, so you would think he'd have been a reliable rusher for Dallas.
When he came to Dallas, that all changed. He only rushed for 432 yards, playing in 13 games. For the price they paid, they could have gone out and signed a young player with potential or drafted a running back in the later rounds of the draft to throw into the mix. The Cowboys failed to see George was declining, making this decision a poor one.
14 Never Should've Drafted: Bobby Carpenter (LB)
As a first-round draft pick, the expectations are for you to eventually become a starter, and play a crucial role on the team. Well, Bobby Carpenter was never able to do that. Throughout his four years in Dallas, he only started three games, and the Cowboys declined to re-sign him. Within those four years, he had a total of 72 tackles and 3.5 sacks. His numbers through four years are what coaches would have wanted to see in one year. He mostly played on special teams throughout his time, but failed to play a role on the defensive side of the ball. In 2008, the Dallas Cowboys were the team to be featured on Hard Knocks. During the show, Carpenter was constantly getting manhandled by right tackle Marc Colombo. During practice, Colombo started calling Bobby, “Barber Carpenter.”
13 Never Should've Signed: Ryan Leaf (QB)
It’s hilarious to think about how Ryan Leaf and Peyton Manning were once mentioned in the same conversation. Leaf turned out to be a complete draft bust, just as Manning turned out to be one of the best quarterbacks to ever live. Leaf really wasn’t good off the field either. He would skip meetings, had a poor attitude, and just didn’t have the mentality of a NFL quarterback. The Dallas Cowboys were Leaf’s last hope of being a starting quarterback in the NFL.
When Quincy Carter went down with an injury, Leaf came in to be the new starting quarterback until Carter came back. In the four games that he played, he threw for 494 yards, one touchdown pass and three interceptions. In each of his four appearances, the Cowboys lost. Unsurprisingly, he was released shortly before the following season.
12 Drafted: Matt LaFleur (TE)
Jay Novacek was one of the staples of the Cowboys' championship offense throughout the 90s. Once he retired, Jones had to look for a replacement, but unfortunately he made a poor choice in drafting David Lafleur. Given that Lafleur was taken 22nd overall, the Cowboys expected him to step in and start right away. Lafleur played in Dallas for four seasons and was a huge disappointment, managing to haul in 200 receiving yards just once in a season. He did manage 12 touchdown catches in four seasons, but it didn't take the Cowboys long to find out he was no Novacek. Fortunately the team solved their tight end problems when they drafted Jason Witten in 2003.
11 Signed: Mike Vanderjagt (K)
Why the Cowboys would sign a kicker to a three-year deal worth $5.4 million baffles many fans, but it was definitely one of the worst signings they have made in their history. Before signing with the Cowboys, Mike Vanderjagt had the best field goal percentage in NFL history. While that sounds great, those leaders always change. Not only were the Cowboys shocked with how poor Vanderjagt was playing, he must have been shocked too. It was the worst season of his career, finishing 13 for 18 with a 72.2% field goal percentage.
When you invest that type of money into a kicker, you immediately think it becomes the least of your issues. But due to the fact that Vanderjagt was struggling, he only lasted one year in Dallas.
10 Drafted: Quincy Carter (QB)
The Cowboys selected Quincy Carter with the 53rd overall pick in 2001. The Cowboys didn't have a first round pick that year, but were looking for a quarterback to replace the recently retired Troy Aikman. The move actually looked brilliant at first, as Carter beat out veteran Tony Banks for the starting job, but his play but injuries cut his rookie season short. The following season, Carter lost his starting job to rookie Chad Hutchison after getting into an argument with Jerry Jones on the sidelines. Arguing with the owner usually isn't a good idea... Carter managed to lead the Cowboys to a playoff berth in 2003, thanks to the tutelage of Bill Parcells. Despite his promising season, Parcells cut Carter the following summer, reportedly due to drug use. Carter's career fizzled out from there.
9 Signed: Marcellus Wiley (DE)
There’s no denying the fact that Marcellus Wiley was a really good defensive end before he came to Dallas. But just a year before the Cowboys signed him, he struggled, only sacking the quarterback three times while starting a full season. The Cowboys thought that he could start a new career there, agreeing for a four-year deal, worth $16 million. While the Cowboys were prepared to spend a future with Wiley, he couldn’t even get through a year with the Cowboys. After only reaching three sacks once again in Dallas, his time was done there.
It seems like it would be a steal considering his value decreased with a bad season during his contract year, but sometimes that actually shows that those players are declining. After Wiley left Dallas, he never had another sack in his career.
8 Drafted: Randy Gregory (DE)
If you didn’t know already, the Dallas Cowboys are known for taking players that have off the field issues. Another one of those guys is defensive end, Randy Gregory. Gregory was initially projected to be a top five draft pick, until he failed a drug test, and slipped to the second round, dropping into the hands of Mr. Jerry Jones.
Between injuries and his character, we still have yet to see what Randy Gregory is truly capable of. Throughout two seasons, he has only played 14 games. And throughout those 14 games, he has only recorded one sack. Gregory is currently suspended indefinitely by the NFL for violating the substance abuse policy. The Cowboys may never see Gregory again, but still remain hopeful that he will play once again. It seems like a lot of trouble for a guy who has only recorded one sack throughout his career.
7 Signed: Greg Hardy (DE)
Many consider Greg Hardy as the worst signing in Dallas Cowboys history. Before being signed by the Cowboys, this team knew that Hardy was trouble. He was supposed to be suspended the first 10 games of his Cowboys career due to a domestic violence case. The NFL ended up reducing his suspension down to only four games. His production wasn’t all that bad, but for what he was getting paid, $11.3 million, the Cowboys expected a lot more of him.
Through 10 games, Hardy had one interception and six sacks. For missing four games, he didn’t have himself that bad of a season. But his off the field issues continued, as he was saying negative things about Jason Garrett. The Cowboys decided not to bring him back. Even with the talent he had, it wasn’t worth the aggravation.
6 Drafted: Byron Jones (S)
Now that we’re getting near the top five, a lot of these decisions were poorly made because of the Cowboys coaching staff. Byron Jones was selected as the 27th overall draft pick of the 2015 NFL Draft. The key thing in Jones being a poor pick, was the fact that he was a cornerback in college. Once he came to the NFL, the Cowboys switched him over to the safety position. Now, many times cornerbacks can do that transition, but how effective they are is another question. Jones is really athletic, which is why he was drafted and used to play the cornerback position. Sadly, he doesn’t have the size or ability to cover tight ends down the field, and so far, has struggled his whole career doing so.
If Jason Garrett moved him back over to cornerback, there’s a chance that Jones could be a major contributor on this team. But since he’s stuck at the safety position, it’s unlikely that we will see a career for him in Dallas.
5 Signed: Brandon Carr (CB)
In 2012, the Dallas Cowboys signed Brandon Carr to a five-year deal worth $50 million. Throughout his career in Kansas City, this looked like a pretty good move. The Cowboys were always desperate for a true stud at cornerback, and Carr was supposed to be that guy. Through his career in Dallas, he had seven interceptions and 48 passes deflected. His numbers were astonishingly better in Kansas City, and that was playing one less year than he played in Dallas. His best season came in 2013, but he started aging, and the contract seemed worse and worse. Bu, Dallas kept him because he was serviceable. But due to his contract, it was hard to ever spend the money to bring in a cornerback to replace him. Carr ended up having a decent season in 2016, but Dallas decided not to bring him back for another season. In his first season with Baltimore, he played better than he had ever played in Dallas.
4 Drafted: Terrance Williams (WR)
What once seemed like the best wide receiver corps in the NFL is now a group that lacks a playmaker. With talks of who is the problem within the wide receiver group, there are so many different ways to point fingers. One solution that would help this team, would be to release Terrance Williams. The Dallas Cowboys drafted Williams in the third round of the 2013 NFL Draft. For a majority of his career, he has remained as the second wide receiver, behind Dez Bryant.
While we have seen a very productive Terrance Williams, we have also seen a struggling wide receiver. In 2017, Williams was unable to record a touchdown, and was the cause of quite a few interceptions. Unlike using his hands, a lot of times he tries to use his body to catch the football, which led to some costly turnovers throughout the season. The Cowboys need another wide receiver that can be a real threat to help relieve some of the pressure off of Dez Bryant.
3 Signed: Nolan Carroll (CB)
With the Cowboys losing four of their starters in the secondary after the 2016 season, they immediately needed to grab as many secondary players as possible. The leader of the group was supposed to be veteran cornerback Nolan Carroll from the Philadelphia Eagles. Carroll and the Cowboys agreed to a three-year deal worth $10 million. While the Cowboys drafted a very young secondary, Carroll was supposed to add some experience to this defense. Carroll began the season struggling, and suffered a concussion against the Denver Broncos in week two. He was inactive for the next three games, and then was released by the team in early October.
Carroll never played more than six quarters in a Cowboys uniform, and may have been the biggest waste of money the Cowboys ever spent. The Cowboys could have stuck with him for a bit longer to see how he would progress when he came back from his injury, but it seems that they were impatient, and content with their rookies.
2 Drafted: Morris Claiborne (CB)
The Dallas Cowboys actually moved up in the 2012 NFL Draft, and traded with the St. Louis Rams for the 6th-overall draft pick in order to select Morris Claiborne. The stakes were high for a team that was looking for that star cornerback, but they never got him. Claiborne was injury-prone throughout his time in Dallas, even in his best season in 2016 when the Cowboys made it to the playoffs. Even if he had the talent to play at a high level, he was always missing playing time. Throughout his Cowboys career, he played 62 games out of a possible 80. And when he played, he wasn’t playing at the level the Cowboys front office thought he would have played.
Some players that the Cowboys would have loved to have instead that they could have selected, include Luke Kuechly, Stephon Gilmore and Fletcher Cox. Instead, they drafted a cornerback who couldn’t stay healthy, and they let move on after their contract was finished.
1 Signed: Rolando McClain (LB)
It’s a shame that some players cannot abide by the rules of the NFL and the law. Linebacker Rolando McClain, has been in trouble with the law all throughout his career in Dallas. From being arrested, to now being suspended indefinitely by the NFL for failing a drug test, it’s been a rollercoaster ride for the linebacker. The issue is that McClain plays really well when he’s on the field for Dallas. Because of that, the Cowboys have counted on him coming back and providing that production.
The issue is, McClain hasn’t stepped foot on the field since 2015, and will probably never play for the Cowboys again. In his time on the field though, he looked like the perfect replacement for Sean Lee when he missed time due to injuries.