The free agent market place is a bit of a gamble for all NFL teams with some hitting home runs on amazing deals and others swinging and missing on horrible deals.
Some deals are worse than others, however. Far worse. And we’re not just talking sub par contracts or teams being locked into dead years late in contracts; we’re talking about franchise-altering mistakes where teams lose money and receive little to no production.
So with free agency on the horizon here in 2019, we look back on the 15 worst free agent deals in NFL history.
15. Matt Flynn, Seattle Seahawks (2012)
After sitting and learning behind Aaron Rodgers in Green Bay, Matt Flynn became a hot target in 2012 with many experts viewing him as a franchise quarterback of the future. The Seattle Seahawks agreed with those projections and signed Flynn to a three-year, $26 million deal, but that was as far as things ever got. Flynn wasn’t able to beat out rookie Russell Wilson for the starting job and the rest is history. Flynn was traded to the Oakland Raiders a year later and Wilson remains under center in Seattle.
14. Larry Brown, Oakland Raiders (1996)
Fresh off a Super Bowl XXX MVP performance, the Oakland Raiders signed Larry Brown to a five-year, $12 million deal with $3.5 million guaranteed — numbers that were significant at the time. However, the investment would fall flat as Brown was never able to recapture his Super Bowl magic. He would appear in just 12 games (one start) over two seasons with the Raiders, recording one interception, which matched the total number of times he was suspended by the team for conduct detrimental. Brown was waived prior to the 1998 season.
13. Neil O’Donnell, New York Jets (1996)
In 1995, Neil O’Donnell led the Pittsburgh Steelers to Super Bowl XXX and used that to cash in the following offseason, signing a five-year, $25 million deal with the New York Jets. He went 0-6 out of the gate and was later lost for the season due to a shoulder injury. He returned the following year, but eventually lost his starting job to Glenn Foley. After refusing to take a pay cut or renegotiate his deal, then-Jets head coach Bill Parcells decided to pull the plug, releasing O’Donnell in 1998. He went a combined 8-12 as the Jets’ starter.
12. Javon Walker, Oakland Raiders (2008)
During the early part of his career with the Green Bay Packers, it was obvious to anyone watching that Javon Walker was talented and had the potential to break out. He finally did in 2004, but injuries slowed him down in 2005 and then again in 2007 when he was with the Denver Broncos. But that didn’t stop the Raiders from signing Walker to a six-year, $55 million contract in 2008. Once again however, injuries got the best of Walker, who recorded just 32 receptions for 196 yards and one touchdown, and then had to be talked out of retirement by Al Davis. That return was short-lived as Walker appeared in just three games in 2009 before being released.
11. Dana Stubblefield, Washington Redskins (1998)
After recording a career-high 15.0 sacks for the San Francisco 49ers in 1997, the Washington Redskins gave Dana Stubblefield a six-year, $36 million deal. The signing seemed like a can’t miss, but the Redskins were wrong. Stubblefield immediately fell off, recording just seven sacks over three seasons before being released in early 2001. Stubblefield returned to the 49ers after that, but never recaptured that 1997 magic.
10. Alvin Harper, Tampa Bay Buccaneers (1995)
Alvin Harper thrived in a secondary role with the Dallas Cowboys, drawing favorable matchups alongside Michael Irvin. That eventually led him to a big contract — four years and $10.6 million with the Tampa Bay Buccaneers. However, Harper regressed dramatically as a No. 1, seeing his production plummet in only two seasons. After recording just 65 receptions for 922 yards and three touchdowns in two seasons, the Buccaneers cut their losses and cut Harper.
9. Jeff Garcia, Cleveland Browns (2004)
Jeff Garcia had three Pro Bowl seasons with the San Francisco 49ers before being let go following a down year in 2003. He was promptly picked up by the Cleveland Browns, who signed him to a four-year deal worth $25 million. However, it quickly became evident that his 2003 campaign wasn’t an exception to the rule, but the new rule itself. Garcia went 3-7 in 10 starts for Cleveland and was released after just one year.
8. David Boston, San Diego Chargers (2003)
Throughout the duration of his rookie contract with the Arizona Cardinals, David Boston ascended, eventually catapulting himself to the top of the list for wide receivers. That ultimately earned him a seven-year, $47 million contract from the Chargers, but they never quite got their money’s worth. Boston did put up solid numbers, but developed a reputation for having a lackluster attitude and was even suspended for cursing out one of the team’s assistant coaches. After just one year, he was traded to the Miami Dolphins.
7. Andre Rison, Cleveland Browns (1995)
Andre Rison was a superstar before the Cleveland Browns and, briefly, after he left Cleveland. However, his one year with the Browns may be considered the most devastating in NFL history. Rison didn’t just fail to live up to his five-year, $17.078 deal, but owner Art Modell had to take out loans to pay Rison’s $5 million signing bonus. At the end of the year, Rison ripped Browns fans to shreds and cheered the team’s move to Baltimore, but he wasn’t brought along for the ride.
6. Jerry Porter, Jacksonville Jaguars (2008)
In 2004 and 2005, Jerry Porter really began to flash for the Oakland Raiders, leading many to believe he was ready to become a consistent WR1. However, a regime change in Oakland led to a rift with Porter, who missed the majority of the 2006 season as a form of punishment after speaking out against Art Shell. Porter would get back on the field after Shell was fired, but became a free agent just a year later, signing a six-year, $30 million deal with the Jaguars. Porter would record 11 receptions for 181 yards and one touchdown through 10 games and was cut after the season. He never played in the NFL again.
5. Daryl Gardener, Denver Broncos (2003)
During the early part of his career, Daryl Gardener, a first-round pick in the 1996 NFL Draft, was a monster in the middle. He was a quality all-around interior defender whose size made him a forced to be reckoned with. That is exactly what the Denver Broncos expected to get when they signed him to a seven-year, $35 million deal, but the elation was short-lived. Gardener was involved in a brawl at a Colorado IHOP that led to wrist surgery, he was twice suspended for conduct detrimental to the team, repeatedly took himself out of games and refused to practice.Ties were ultimately cut after a few incidents with teammates. He recorded just five tackles in five games.
4. Deion Sanders, Washington Redskins (2000)
Deion Sanders is one of the greatest defensive backs to ever play in the NFL, but when the Redskins signed him to a seven-year, $56 million deal in 2000, he already had one foot out the door. In exchange for that hefty investment, Sanders provided Washington with just 38 tackles, four interceptions and one forced fumble. He officially retired from football at the end of the 2000 campaign, but returned four years later to play for the Baltimore Ravens.
3. Nnamdi Asomugha, Philadelphia Eagles (2011)
After three straight Pro Bowl seasons for the Oakland Raiders, Nnamdi Asomugha was considered a prized free agent in 2011 and was being chased by a large number of teams. But it was the Philadelphia Eagles who ultimately landed Asomugha on a five-year, $60 million deal, which led to the “Dream Team” label. But Asomugha’s Pro Bowl talents quickly proved to be a thing of the past as he was repeatedly burned in his two seasons with the Eagles, who cut bait and ran at the end of 2012 season.
2. Brock Osweiler, Houston Texans (2016)
After an extensive search for a franchise quarterback, the Houston Texans settled on Brock Osweiler in 2016, signing him to a four-year, $72 million deal with $37 million guaranteed. However, the former second-round pick of the Denver Broncos struggled mightily in his first (and only) season as a full-time starter, completing just 59% of his passes for fewer than 3,000 and 15 touchdowns to 16 interceptions. Realizing the err of their ways almost immediately, Houston shipped Osweiler and some draft picks off to the Cleveland Browns in March of 2017, saving them from having to honor the entirety of a nightmare of a contract.
1. Albert Haynesworth, Washington Redskins (2009)
Entering free agency in 2009, Albert Haynesworth was considered by many to be one of the elite players available despite a long history of questionable on-field incidents. Those concerns were dismissed by Washington Redskins owner Daniel Snyder, who promptly approved a seven-year, $100 million deal for Haynesworth. But the story fell sour from the get-go as Haynesworth butted head with the coaching staff and his teammates, refused to practice and had little to no impact on the field. It took only two seasons for Washington cut their losses and ship Haynesworth off to the New England Patriots for a fifth-round pick after he had been placed on the team’s restricted list.
