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Top 25 Worst NFL Free Agency Signings of All Time

The NFL offseason has started and quickly teams have lost their minds with massive contracts and team-altering trades kicking off one of the more eventful offseasons in recent memory. The NFL, more so than any of the other major American sports leagues, is a league where teams can go from four wins and last place in their division to an 11-win playoff team in just one season, in part because of free agency. The NFL has a "hard" salary of cap of $143.2 million, meaning that unlike other leagues where teams can go over the cap but are forced to pay a tax, the NFL offers no such luxury. This often forces successful teams into tough decisions about who to keep on the roster.

The NFL also has a hard salary floor of about 90% of the cap, meaning that teams are forced to spend a certain amount which encourages all teams to be active in free agency so teams like the Raiders and Jaguars who are massively under the cap can afford to overspend in order to lure players to their teams. The structure of NFL contracts also makes free agency exciting, with very few players end up playing out their entire contracts, instead being released by teams to save cap space which leads to a pool of viable players every season coming available. This spending frenzy can lead to some bad, short-sighted decisions by teams and owners looking to make a big splash in free agency which is generally not the optimal way to build a team. While teams can use the offseason to add that final key piece, as the Patriots did with Darrelle Revis this past season, they can also set their franchise back by making a few moves that don't pan out. The following list are the top 25 free agency moves that NFL teams would love have back.

25 25. Antwaan Randle El

via yardbreaker.com

Randle El is a former college quarterback that was drafted by the Pittsburgh Steelers as a wide receiver who knew they could use his unique skill set in interesting ways. He found success with the Steelers using his athleticism to affect the game in a multitude of ways, most often in special teams as a kick returner. Randle El displayed his former QB skills in Superbowl XL tossing a 43-yard touchdown in the Steelers victory. A theme you will see throughout this list, overpaying for recent Super Bowl winners, the Redskins, who you will also see often in this list, saw that play and offered him a seven-year deal for $31 million, with an $11.5 million signing bonus despite primarily excelling as a special teams role player. Randle El would go on to only exceed 600 yards receiving in one of his four seasons with the Redskins before being released.

24 24. Jake Delhomme

via cleveland.com

23 23. Dana Stubblefield

via yardbarker.com

22 22. Ahman Green

via nfl.com

21 21. Deion Sanders

via solecollector.com

20 20. Bruce Smith

via ibtimes.com

19 19. Jerry Porter

via complex.com

18 18. Daryl Gardener

via yardbarker.com

17 17. Adam Archuleta

via nflrt.com

16 16. Mike Vanderjagt

via yardbarker.com

15 15. Jairus Byrd

Derick E. Hingle-USA TODAY Sports

14 14. Laurent Robinson

via nsafootball.com

13 13. Alvin Harper

via nfl.com

12 12. Jeff Garcia

via nfl.com

11 11. T.J. Houshmandzadeh

via nflrt.com

10 10. Larry Brown

via complex.com

The Raiders and the Redskins like to challenge each other for worst free agency spending. Larry Brown was a Dallas Cowboys cornerback that parlayed an unlikely Superbowl MVP award into a massive new contract with the Raiders in 1996, five years for $12.5 million (a good chunk of money at that time). During that Super Bowl, Brown intercepted two Neil O’Donnell (next on this list) passes to help the Cowboys to the championship, but not all interceptions are created equal and these two were gifts thrown right to him by a struggling quarterback.

9 9. Neil O'Donnell

via nfl.com

8 8. Andre Rison

via sikids.com

Andre Rison recorded over 1,000 yards receiving in four of his five seasons with the Atlanta Falcons before being wooed to play for the Cleveland Browns. Cleveland gave Rison $17 million over five years, but would he would go on to play only one year with the team. Rison struggled with injuries and attitude issues as it appeared he was not giving much effort.

7 7. David Boston

via basketballforum.com

6 6. Javon Walker

via yardbarker.com

There have been many Raiders on this list, but Javon Walker stands out as the worst one. Walker had built a strong career playing in good offenses in Green Bay and Denver, but had been dealing with injuries in 2007. In 2007 Walker struggled with injuries and caught 287 yards and no touchdowns at age 29.

5 5. LeCharles Bentley

via cbscleveland.com

LeCharles Bentley was a solid lineman early in his career with the Saints, making the Pro Bowl twice, at both guard and center. Bentley hit free agency in 2006 and his hometown Cleveland Browns saw an opportunity to bring home one of their own and offered Bentley the largest contract ever at the time for a center; $36 million, with $12.5 million guaranteed.

4 4. Nnamdi Asomugha

via pennlive.com

Sometimes a front office and coaching staff combine to make some puzzling decisions. After spending his early career with the Raiders and building a reputation as the best man-to-man cornerback in the league, Asomugha hit free agency as one the biggest targets in recent years. Nnamdi was the biggest signing in a flurry of Eagles moves that led Vince Young to coin their team, the Dream Team. Looking back its even more ludicrous that the signings of Vince Young, Asomugha, Jason Babin and Cullen Jenkins led to being called a Dream Team.

3 3. Antonio Bryant (twice)

via dallasnews.com

Some players are such dynamic athletes and show just enough flashes of their talent that teams continue to make the mistake and fall for their potential. After a solid season in Cleveland where he put up a modest 1,009 yards and four touchdowns, the 49ers signed Bryant to a four-year $14 million contract. Bryant would go on to struggle both on and off the field, failing multiple drug tests and being released from the team in 2007.

2 2. Jeremiah Trotter

via bleacherreport.com

We may be piling on, but the Redskins and Dan Snyder did this to themselves. Sometimes it's not just that a free agent isn't as good as you thought, it's that the organization he goes to does not have the infrastructure in place for him to succeed. Trotter was named to four Pro Bowls during a very productive career with the Eagles and entered free agency after his career best season with 93 tackles, 10 passes defended, and 3.5 sacks.

1 1. Albert Haynesworth

via performgroup.com

Albert Haynesworth was a dominant force with the Titans when he was on the field but showed signs of chronic injury issues and attitude problems. Coming off two consecutive Pro Bowl seasons as a dominant run stopper and interior pass rusher, the Redskins and Daniel Snyder offered a massive seven-year, $100 million contract. Haynesworth's tenure with the Redskins started off rocky as he gained weight, fought with the coaching staff, showed his frustration with the 3-4 scheme that new coach Mike Shanahan was putting in, and failed fitness drills before his first season.

There was even one instance in which he remained on the ground during a live play and refused to get up because he was too lazy. Haynesworth has since said that he lost his love for the game during his tenure with the Redskins and regrets leaving his situation with the Titans. Haynesworth tallied 6.5 sacks in two seasons before getting released and spending a few months with the Patriots and Buccaneers before leaving the league.

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Top 25 Worst NFL Free Agency Signings of All Time