The 8 Worst And 7 Best Signings In Dallas Cowboys History

Free agency is arguably the most exciting time for football fans when football isn’t being played. Unlike the three other major sports, it is rare to see a top talent player sign with a new team but when it does happen, it creates major storylines heading into the next season. Every year, some teams attempt to make the big splash in free agency signing the most well-known players to an astronomical amount of money, while other teams are barely heard of during the free agency period. The Dallas Cowboys often reside as one of the teams who rarely give out large contracts to free agents.

America’s Team hasn’t seen a Super Bowl championship since the middle of the 90s. During that time frame, the team prided themselves on drafting well and adding the right players through free agency. That strategy led the team to three championships with hardly any complaint from the fans.

As of late, however, the team has been best described as average winning just two playoff games since 1996. Dallas has often shied away from the big names in free agency and has instead given a large amount of the team’s salary cap to home grown talent. When the Cowboys have landed free agents on the market, many have proven to be more hurtful than helpful when it comes to the team’s success.

People around the league would expect the Cowboys to be one of the better teams come free agency, but they have strayed from their winning ways in the 1990s.

Here are the eight worst and seven best free agent signings in Dallas Cowboy history:

15 Worst - Eddie George

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Eddie George was one of the greatest players to ever wear the Tennessee Titans’ uniform. In seven seasons with the team, George never missed a start and became the second running back in league history, joining Jim Brown, as the only players to rush for over 10,000 yards without missing a start. Following ankle/toe injuries and a decline in production during the 2003 season, George was released from the team.

The Cowboys signed George to a 1 year $1.5 million contract with incentives that could earn him up to $4.25 million dollars. Unfortunately for George, he would never come close to the numbers needed to achieve incentives in his contract. He started just eight games for the team during the 2004 season, totaling 432 rushing yards and 4 touchdowns. His declined production made the decision easy to hand the starting job to rookie Julius Jones.

14 Best - Deion Sanders

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Deion Sanders was one of the most dynamic defensive players to take the field in the late 1990s and early 2000s. Sanders spent four seasons with the Atlanta Falcons and then a one year stint with the San Francisco 49ers where he helped the team win Super Bowl XXIX. Sanders was also a successful outfielder for five teams during his 11-year baseball career. He hit for a career average of .263 and 39 home runs. Following his Super Bowl victory in 1995, he joined the Dallas Cowboys after seeing interest from several franchises.

Sanders signed a seven-year $35 million contract and proved to be worth every penny. He decided to sign with the Cowboys because of his close relationship with wide receiver Michael Irvin and saw his chance to repeat as a Super Bowl champion. Sanders missed the first 8 weeks of the season but returned against his former team (Atlanta Falcons) in week nine. He went on to lead the Cowboy’s defense to another Super Bowl championship. He made the Pro Bowl for the team the next four seasons, but was released in 2000 due to salary cap troubles.

13 Worst - Mike Vanderjagt

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Mike Vanderjagt played eight seasons for the Indianapolis Colts and led the NFL in scoring in 1999. Before signing with the Cowboys, he was regarded as the most accurate kickers in NFL history percentage wise. However, Vanderjagt missed a game tying field goal against the Steelers in the playoffs costing the team a chance at overtime. After making comments about the team during the 2005 offseason, the Colts decided to let him walk as a free agent.

The Cowboys were not known to pay kickers big money but made Vanderjagt the highest paid kicker in franchise history when they gave him a three year deal worth $5.4 million. In just ten games with the team, Vanderjagt converted just 13 out of 18 field goal attempts, including two misses against the Indianapolis Colts. The Cowboys went with Martin Gramatica for the rest of the season and Vanderjagt has not seen an NFL snap since.

12 Best - Leonard Davis

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Leonard Davis is one of a few players on this list who did not have an attractive background before signing with the Dallas Cowboys. Davis started his NFL career with the Arizona Cardinals playing various positions across the offensive line. In 2004, he was moved to left tackle and remained there until his release in 2007. During his tenure with the Cardinals, Davis was one of the highest penalized lineman in the NFL.

In what many experts around the league considered to be a puzzling move, the Dallas Cowboys signed Davis to a seven-year $49.6 million deal. During that time, Davis was the highest paid player in the NFL making $25.4 million. He started at right guard for the team and made the Pro Bowl in his first three seasons with the team and helped the team win the NFC East twice during his four seasons with the team. He was released following the 2010 season due to declining play.

11 Worst - Terrell Owens

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Many people would argue that Terrell Owens was one of the better free agent signings because of his production on the field, but his issues off the field made it impossible for quarterbacks to work with him. He left the Philadelphia Eagles following the 2005 season after being suspended four games and deactivated for the rest of the season. He was constantly taking jabs at management for not renegotiating his contract and quarterback Donovan McNabb for coming up small in the Super Bowl.

The Cowboys signed Owens to a 3-year $25 million deal during the 2006 offseason. Owens racked up an impressive 38 receiving touchdowns and three straight 1,000 receiving yard seasons. However, his off the field issues kept him from staying in Dallas any longer. He would constantly get into fights on the sideline about not being targeted enough and even broke down crying at the podium after losing to the Giants in the NFC divisional round in 2007. Even with his off the field issues, we will see Owens in the Hall of Fame some day.

10 Best - La'Roi Glover

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La’Roi Glover was one of the best defensive lineman in the 2000s by most people’s standards. He totaled 83.5 sacks during his career and was voted to the 2000’s All-Decade Team. With the Saints in 2000, he led the NFL with 17 sacks which was second most all-time by a defensive tackle. After an impressive five-year run with the Saints, Glover tested the free agent market.

The Cowboys wasted no time and immediately signed Glover to a five-year $22.5 million deal during the 2002 offseason. Glover made his impact felt immediately on the Cowboys’ young defensive line. He played in all 64 games with the Cowboys and became the first Dallas player to make the Pro Bowl in each of his first four seasons with the team. He helped bring the team back to the playoffs after consecutive 5-11 seasons before he arrived.

He saw his role diminish in his final season with the team and signed with the St. Louis Rams for his final three years in the NFL.

9 Worst - Greg Hardy

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The signing of defensive end Greg Hardy threw a target on the Cowboys' back that they certainly did not need. Hardy stood out as one of the league’s best pass rushers during his early years with the Carolina Panthers including a 15 sack year in 2013. During the 2014 offseason, Hardy was arrested on assault charges for allegedly choking his girlfriend and threatening to kill her. He played in just one game for the Panthers in 2014 and was soon placed on the NFL exempt list.

After losing to the Packers in the NFC Divisional playoffs in 2014, the front office thought they were a star-on-defense away from making it to the next level. That star, unfortunately, was recently suspended Greg Hardy. The Cowboys signed Hardy to a 1-year $11.5 million deal. After serving his four game suspension, Hardy showed glimpses of his former self early on with great performances against the Patriots and Seahawks but began to prove himself not worthy of the contract in the coming weeks. Hardy was constantly showing up late to meetings and posting inappropriate tweets. The Cowboys did not re-sign him for the 2016 season.

8 Best - Jay Novacek

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If Jason Witten had not gone on to have the Hall Of Fame career he has had, then Jay Novacek would be known as the greatest tight end in Cowboy history. Novacek spent his first five seasons with the Arizona Cardinals but never emerged as a top tier tight end in the league. When the team no longer considered a good fit for their scheme, Novacek was allowed to walk in free agency.

The Cowboys signed Novacek to a three-year $4.8 million deal in 1990. Troy Aikman, Emmit Smith, and Michael Irvin typically get credit for the dynamic play from the Cowboys’ offense in the 1990s but Novacek was often referred to as Aikman’s security blanket. He became a five-time Pro Bowler with the team and helped the team win their three Super Bowl Championships in the 90s.

7 Worst - Brandon Carr

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As a 5th round pick, there was never very high expectations for cornerback Brandon Carr after the Chiefs drafted him. Once he found his way into the starting lineup, it was difficult to take him off the field. He totaled a career high four interceptions in 2011 which turned out to be his final season with the Chiefs. Carr expected to have a huge market when hitting free agency in 2012 and the Cowboys certainly gave him what he wanted.

The Cowboys signed Carr to a five-year $50 million deal. Even though he played through his entire contract, Carr never lived up to his enormous signing. In five years with the team, he totaled just 7 interceptions which averaged just over one interception per season. He never proved to be the shut down corner the Cowboys had hoped for and is still looking for a new team today.

6 Best - Ray Donaldson

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Ray Donaldson played 16 seasons in the NFL, but did not see his first Super Bowl win until after he joined the Cowboys in 1995 at the age of 36. Donaldson spent his first 13 years in the NFL with the Colts franchise, trailing only Johnny Unitas for total number of years with the Colts. After being released at the age of 35, he joined the Seahawks and helped them lead the NFL in rushing for the first time in franchise history.

In 1995, Donaldson signed with the Cowboys on a two-year $1.6 million deal. At the age of 37, Donaldson was the oldest center in the NFL while playing for the Cowboys. Although he was unable to play in Super Bowl XXX, the team won and helped him achieve his first Super Bowl ring. He made the Pro Bowl in both seasons with the team and retired at the age of 38.

5 Worst - Ryan Leaf

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How would anyone expect Ryan Leaf not to make this list? He is always mentioned at the top of list when thinking of the biggest busts in NFL history. Leaf went number two overall in the 1998 draft after Peyton Manning. It is hard to believe that there was ever even a debate between the two of them leading into the draft. Leaf spent just three seasons with the Chargers before letting him walk.

Leaf signed with the Cowboys in 2001, but failed his physical before his reign as a Cowboy quarterback could even begin. However, starter Quincy Carter got hurt and the team re-signed Leaf in the middle of October. Leaf lost all four games he played with the Cowboys totaling just one touchdown and three interceptions. After calling it quits at the age of 26, Leaf is often regarded as the biggest bust in league history.

4 Best - Kyle Kosier

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Kyle Kosier went under the radar as a 7th round pick in 2002. After playing three years with the San Francisco 49ers primarily on special teams, Kosier spent one year in Detroit switching between guard and tackle throughout the year. Known mainly as a journeyman lineman, Kosier wasn’t expecting to be a hot name come the free agency period.

Kosier signed a 5-year $15 million deal with Dallas in 2006 where he would eventually finish out his career. He started 80 games during his tenure with the team and played most of his career at left guard. He even saw a 3-year extension after his first free agent contract ran out. He was known to be one of the vocal leaders of the Cowboys as well as one of the main signal callers on the offensive line.

3 Worst - Brandon Weeden

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Brandon Weeden will forever be known as one of many draft busts made by the Cleveland Browns. Weeded entered the 2012 NFL Draft at the unusual age of 29 after playing professional baseball for four years. Weeded played just two seasons with Cleveland before deciding that anyone else on the roster would be a better option at quarterback.

With Tony Romo constantly finding himself on the shelf, the Cowboys looked to find a backup who could help the team win if called upon. They signed Brandon Weeden to a 2-year $1.4 million deal. He appeared in nine games and started in four of them after Romo got hurt. He lost all three of his starts in 2015 and lost his job as Cowboys backup quarterback to Matt Cassel.

2 Best - Ken Hamlin

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Before the likes of Earl Thomas and Kam Chancellor, Ken Hamlin was the star safety for the Seattle Seahawks defense. He played four seasons with the team totaling eight interceptions and helped the team reach the Super Bowl in 2005. After serious head injuries due to off the field issues, Hamlin was released from the Seahawks and tested the free agent market.

The Cowboys signed Hamlin to a 1-year $2.5 million deal during the 2007 offseason. Hamlin reached his only Pro Bowl the following season accumulating his career high in interceptions with five. The following year he signed a six-year $38 million contract. He led the secondary in tackles in 2008, but only played out two more years of his contract before being released in 2010.

1 1.Worst - Bryant Westbrook

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Bryant Westbrook spent five seasons with the Detroit Lions before hitting the free agent market. He was not a star corner by any means but many would consider him an average defensive back. He even recorded six interceptions in 2000, taking one of them back for a touchdown. What doesn’t make sense is the deal the Cowboys offered him following the 2001 season.

Westbrook signed a 1-year $1 million deal with Dallas but only played in one game with the team. He played poorly against the Houston Texans and was benched in the second half. Even with one poor performance, it shouldn’t have been enough to lose a job with a team. The Cowboys cut Westbrook after just one game and would later be picked up by the Green Bay Packers.

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