5 worst free agency signings in Dallas Cowboys history feat. Mike Vanderjagt

The Dallas Cowboys enter the 2025 offseason with a few areas to strengthen. However, they have made a few torrid decisions with free agents over the years.

On that note, here's a look at the five worst free agents that the Cowboys signed since their inception.

Listing 5 worst free agent signings in Dallas Cowboys history

NFL: Former Dallas Cowboys QB Brandon Weeden - Source: Imagn

#5. Brandon Weeden, QB

The Dallas Cowboys signed Weeden in the 2014 offseason on a two-year contract. The quarterback got his opportunity to showcase his talents after Tony Romo's injury, but lost three of his four starts at Dallas.

Weeden then lost his place to Matt Cassel in the 2015 season before the Cowboys released him.

#4. Ryan Young, RT

Young signed a three-year deal worth $6.5 million with the Cowboys in 2003, which included a $2 million signing bonus. However, he was able to play just one season with the team.

Young had a knee injury even before he arrived at Dallas and the issue persisted in his sole season with the team. The right tackle played 11 games for the Cowboys before being waived in March 2004.

#3. Mike Vanderjagt, K

Vanderjagt signed a three-year, $4.5 million deal with the Cowboys in March 2006. His contract included a $2.5 million signing bonus. However, he played just one season with the team.

During his time at Dallas, Vanderjagt made 13 of 18 field-goal attempts and made two of five FGs from 35 yards or more. He failed to convert some critical kicks for the Cowboys, which led to him being released in November.

#2. Bryant Westbrook, CB

Westbrook signed a one-year deal with the Cowboys in 2002 after five solid years as a cornerback for the Detroit Lions. However, his time in Dallas did not go well and ended prematurely.

Westbrook played just one game for the Cowboys against the Houston Texans, in which he was benched in the second half. He was cut from the team on Sept. 12.

#1. Greg Hardy, DE

Hardy inked a one-year, $11.3 million deal with the Dallas Cowboys in March 2015. The defensive end was, however, suspended for the first four games of the season after violating the NFL Personal Conduct Policy.

After a solid first start for the Cowboys against the New England Patriots, Hardy failed to maintain his level of consistency. He was also in the news for inappropriate tweets, frequent tardiness, and being a negative influence on the younger players on the team. The Cowboys did not re-sign Hardy the following year.