NFL Free Agent Signings That Fell Flat

Mike - June 8, 2019

NFL Free Agent Signings That Fell Flat

Mike - June 8, 2019

The free agency period of the NFL has quickly become one of the most awaited events of the sporting year. That’s no surprise, as it is the first major offseason action of a new football year. Fans anticipate their favorite teams’ moves with fervor in the hopes they will actually improve their overall records as a result.

While teams do often find difference-making players on the free agent market, it seems like more often we see high-priced players fail to live up to the almost unattainable hype attached to them due to their free agent contracts. It’s transpired time and time again in NFL history, even with major stars. Some free agent deals, new and old, have simply been franchise-decimating moves that have set teams back multiple years.

We took an in-depth look at the worst such instances in NFL history. Here are the 26 worst NFL free agent signings of all-time:

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26. Cody Parkey, Chicago Bears (2018):

While it is easy to blame Parkey for the Bears’ playoff exit in 2018, his contract was already ridiculous in the first place. He was signed to a four-year contract with $9 million guaranteed that year. He went on to miss 11 kicks last fall and was released by the Bears in March 2019. Problem is, $3.5 million of that is still guaranteed for the 2019 season, meaning the Bears are still paying for the man who many believe cost them their season last winter.

Replays showed that Parkey’s kick was partially blocked, so it wasn’t totally his fault. But 11 missed kicks at that price just won’t cut it in the NFL. The Bears probably wish they’d have signed Parkey to a much more short-term deal, making him one of the worst free agent signings in the NFL.

25. Nnamdi Asomugha, Philadelphia Eagles (2011):

Asomugha was considered a true shutdown corner whom teams rarely chose to throw at during his early-career years in Oakland. After making the Pro Bowl three straight years, the Eagles lavished five years and $60 million with at least $25 million guaranteed on him in their infamous 2011 sending spree.

It did not pay off, as Asomugha was anything but the shutdown defender everyone had come to fear him as in Oakland. He was repeatedly beaten, and the Eagles did not make the postseason in either of his two years with the team. After not agreeing to a restructured contract before the 2013 season, he was released by the Eagles. He played half of one more season in San Francisco.

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24. Fred Smoot, Minnesota Vikings (2005):

The brash Smoot was billed as one of the most effective defensive backs in the NFL when the Vikings signed him away from the Washington Redskins in 2005. Lavishing him with a six-year, $34 million deal at the time, Smoot never came even close to living up to that billing for Minnesota.

In fact, he was more known for reportedly serving a large and influential role in the Vikings’ boat party scandal allegedly involving prostitutes and other unsavory aspects of pro football stardom. Horrific signing, and one that the Vikings quickly wished to erase from their memory after they released him just a single year later.

23. Elvis Grbac, Baltimore Ravens (2001):

The Baltimore Ravens won the Super Bowl in the 2000 season thanks to a historic defense that is legitimately one of the best of all-time. Trent Dilfer was simply a game manager on offense, and they apparently thought they didn’t need him any longer. So they let him walk and decided to pay Grbac a bounty to the tune of five years and $30 million.

He repaid them by throwing more interceptions than touchdowns the following season, with 18 picks to 15 scores. He did lead to the team to a playoff birth and a Wild Card victory over the Dolphins, but his performance was considered a big disappointment. He also threw three interceptions in a season-ending loss to archrival Pittsburgh in the Divisional Round. The Ravens asked him to take a pay cut after the season. He refused and was let go.

22. LaVar Arrington, New York Giants (2006):

Hulking former Penn State linebacker Arrington had some solid years with New York’s divisional rival Washington, so the Giants decided to pay him a king’s ransom to play for them in 2006.

Let’s just say the experiment did not work out. Despite warning signs of obvious injury concerns and reported discord with Washington coach Joe Gibbs, New York signed Arrington to a seven-year deal worth $49 million. He played one year in New York, tearing his Achilles tendon in Week 7 and missing the rest of the year. Arrington was cut after less than a half of a season in New York and retired in 2007.

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21. Mike Glennon, Chicago Bears (2017):

Glennon showed promise as a rookie with the Tampa Bay Buccaneers in 2013, but soon became Jameis Winston’s backup in 2015-2016. His stats and playing time took a precipitous dive in the years after his debut.

For some reason, the Bears decided to sign him to a three-year, $45 million contract despite the fact Winston had clearly replaced him in Tampa. Then, they traded up to select North Carolina product Mitchell Trubisky with the second pick of the draft. Glennon still started ahead of the rookie but was benched after only four games. He resurfaced with the lowly Arizona Cardinals, playing in two games before getting released again. He’s now on the Oakland Raiders for now, but Glennon’s free agent deal is looking like one of the biggest heists in NFL history.

20. Matt Flynn, Seattle Seahawks (2012):

Flynn may be the biggest example of a one-game wonder in NFL history. That one game also led to him becoming one of the biggest free agent busts of all-time. In the final game of the 2011 season, Flynn threw for 480 yards and six touchdowns – both Packers’ single-game records – in a 45-41 win over the Detroit Lions in relief of Aaron Rodgers.

He quickly became one of the hottest free agent commodities and the Seattle Seahawks agreed. They scooped him up with a three-year deal worth $26 million including $9 million guaranteed. However, a wrench was thrown in the plans of making Flynn Seattle’s starter when the team drafted a player named Russell Wilson in the third round of the 2012 NFL draft.

Wilson won the starting job from Flynn in training camp before becoming a Super Bowl winner and the current highest-paid player in the NFL. Flynn and his massive deal became irrelevant. He was released and bounced around from Oakland to Buffalo, back to Green Bay, over to New England and the New York Jets before finally ending his career with New Orleans. Flynn never threw for more than 1,146 yards in a single season.

19. Larry Brown, Oakland Raiders (1996):

Brown straight cashed in on the overbearing hype of his Super Bowl MVP-winning performance in the 1995 season. His Dallas Cowboys squad was loaded with future Hall of Famers, but Brown earned the Super Bowl XXX MVP distinction by intercepting Steelers QB Neil O’ Donnell twice in the pivotal match.

The timing was right, as he was a free agent. He signed a five-year, $12 million contract including $3.5 million guaranteed with Oakland. Those numbers don’t sound huge by any means now, but were solid back in 1996. Regardless, Brown failed to reward his new team for the pay, playing only 12 games and intercepting only a single pass in two years with Oakland – one less than the Super Bowl performance that earned him that fateful contract. Brown was ultimately demoted and even suspended for conduct issues in Oakland. He was later released by the Raiders, moving on to short stints with the Vikings and Dallas again before retiring.

18. Scott Mitchell, Detroit Lions (1997):

In 1993, Mitchell filled in admirably enough when legendary Hall of Famer Dan Marino went down with an injury for Miami, completing 13 passes for 1,773 yards with 12 touchdowns and eight interceptions. He parlayed that into a deal to become Detroit’s starting quarterback in 1994. Despite running an offense featuring running back Barry Sanders and wide receiver Herman Moore, his numbers actually dipped from the previous year, however.

Regardless, Mitchell was given a second chance for the Lions in 1995. He actually played very well with 346 completions for 4,338 yards with 32 touchdowns and only 12 interceptions, all great numbers. But it was that year that ultimately made him one of the NFL’s biggest free agent busts as well. His numbers once again dipped the following year in 1996, but the Lions still thought it wise to hand him a four-year, $28 million contract before the 1997 year nonetheless. He responded with better stats than his 1996 season, but nowhere near that of his career-best 1995. Mitchell was benched for journeyman Charlie Batch in the 1998 season. He flamed out of the NFL after stints with Baltimore and Cincinnati.

17. Neil O’Donnell, New York Jets (1996):

O’Donnell had a decent enough career early on with the Pittsburgh Steelers. The high point of that run was his appearance in Super Bowl XXX, but it ultimately led to two of the biggest free agent mistakes in NFL history involving the aforementioned Larry Brown and O’Donnell himself.

Pittsburgh offered O’Donnell a contract in 1996, but he chose to take the more lucrative path of an offer from the Jets. Signed to a five-year, $25 million deal, O’Donnell promptly led New York to a 0-6 record to start the 1996 season. He was then forced out for the remainder of the year with a shoulder injury. He was replaced by a player named Glenn Foley the following year after head coach Bill Parcells got sick of him. O’Donnell was then released by the Jets after the 1997 season when he refused to renegotiate his contract. He signed on with the Cincinnati Bengals but was eventually replaced in 1999, resurfacing with Tennessee and retiring after the 2002 season.

16. Sean Gilbert, Carolina Panthers (1998):

Gilbert was a monstrous presence on defense in his early years with the Rams and Redskins. When he was named as an alternate for the Pro Bowl in the 1996 season, Washington made him their franchise player with a $3.4 million offer for one year. He didn’t accept it, however, choosing to sit out the 1997 season. The Redskins then chose to franchise tag him again, this time offering a lower $2.97 million salary for the season.

The NFL Player’s Association had an all-day arbitration with the league in 1998 to sort out Gilbert’s unique case. When the dust settled, Carolina offered the hulking tackle $46.5 million to sign with them. When Washington declined to match the massive offer, the Panthers sent two future first-round picks in 1999 and 2000 to Washington for the rights to Gilbert. He repaid them by notching a mere 15.5 sacks during five years with the franchise and was then released in 2003. Gilbert resurfaced with Oakland that season, producing a laughable 7 total tackles. He retired after that year.

15. Dana Stubblefield, Washington Redskins (1998):

This 290-pound defensive tackle from Kansas set the league ablaze in 1997, securing 15 sacks for San Francisco on the way to being named the NFL Defensive Player of the Year by the Associated Press. Washington offered him a six-year contract worth $36 million, which was big money at the time.

Stubblefield never came close to living up to that billing, however, tallying only seven sacks in three years with the club. He was plagued by injuries, yet it was still a disappointing tenure considering he played opposite tackle Dan ‘Big Daddy’ Wilkinson, who was perceived to take some of the heat off Stubblefield by drawing constant double teams. He returned to the 49ers for the 2001 and 2002 seasons and played for Oakland in 2003 before retiring, but could never regain the magic he had in 1997.

14. Alvin Harper, Tampa Bay Buccaneers (1995):

Super-fast Tennessee Volunteer Harper made his way to the Cowboys as a running mate for star receiver Michael Irvin in the first round of the 1991 draft. Harper played a solid, if not featured, role in the Cowboys’ Super Bowl dynasty of the 1990s, steadily increasing his production his first four years with Dallas. That culminated with his impressive showing in 1994, where he caught 33 passes for 821 yards and eight touchdowns, resulting in a ridiculous 24.9 yards-per-reception average.

Tampa Bay saw it fit to give him a four-year, $10.6 million deal before the 1995 season, one that Harper did not live up to. He played in only 25 games in two years with Tampa, catching 65 passes for 922 yards and three touchdowns. He was released following the 1996 season. Harper was then signed by Washington but caught a ridiculous two passes in 1997 before flaming out of the NFL with a return to Dallas, playing only two games in 1999.

13. Javon Walker, Oakland Raiders (2008):

Walker truly broke out in 2004. Racking up 89 catches for 1,382 yards and 12 scores, the hype train was rolling. But he threatened to retire if he was not granted a renegotiated contract with Green Bay after the season. A large standoff ensued, and Walker threatened to hold out before ultimately reporting to training camp. In a rough twist of events, he missed the majority of the season after tearing his ACL in the first game of 2005.

But that’s not why he’s one of the biggest free agent busts ever. No, that came later. Walker was traded from Green Bay to Denver and played two years for the Broncos, one good and one mediocre. The Broncos released him after the 2008 season when they could not trade him. Oakland saw it fit to lavish a six-year, $55 million deal that included $16 million in guaranteed money on Walker. What followed was truly a massive bust, with Walker playing in only eight games and amassing 15 catches for 196 yards and only one touchdown in his sole season with Oakland. He played only three games the following year and had no catches. Ouch.

12. Martellus Bennett, Green Bay Packers (2017):

An enigmatic personality, Bennett was a solid if not spectacular performer at the tight end position for most of his 10 seasons in the league. But when Green Bay signed him to a three-year, $21 million contract before the 2017 season, things got a bit weird.

Bennett reportedly failed to admit he had a torn rotator cuff and labrum in his shoulder and was released by the team. He claimed that the team had pressured to play with the serious injury. Somehow he was signed by the New England Patriots and played on November 12 of that year. He was eventually placed on injured reserve due to the injury on November 27. He was released on March 7, 2018, and retired from the NFL 16 days later. A solid career, but a strange ending that made him a massive free agent disappointment in Green Bay.

11. Ahman Green, Houston Texans (2007):

After two under-the-radar years with Seattle to start his career, Green signed with the Green Bay Packers and truly turned it on to become one of the elite backs in the NFL, rushing for over 1,000 yards in six of his seven years with the team. That included a 1,883-yard, 15-touchdown 2003. Those numbers dwindled to 1,059 yards with five touchdowns in 2006, but Houston still signed him to a four-year, $23 million contract in 2007.

Green only played 14 games in two seasons with the Texans, rushing for 554 yards with only five scores – a large departure from his glory years with Green Bay. He returned to the Packers in 2009 and retired after playing eight games that year.

10. David Boston, San Diego Chargers (2003):

Boston was quite the unique case of a free agency bust. The hulking wideout had two 1,000-yard seasons in his first four years with Cardinals. That led the Chargers to sign him to a massive seven-year, $47 million contract that included $12 million guaranteed in 2003. He put up decent enough numbers, with 70 catches for 880 yards and seven TDs in his only year in San Diego.

But it was his mercurial personality and supposedly uninspiring practice habits that prompted San Diego to send him away for the laughable compensation of a sixth-round draft pick. He was suspended for performance-enhancing drugs before the next season, then tore knee ligaments and missed the entire campaign anyhow.

He had four receptions for 80 yards with Miami in 2005 and was never seen on an NFL field again.

9. Jeff Garcia, Cleveland Browns (2004):

California-born Garcia had some truly great years for San Francisco early in his NFL run, including his magic 2000 and 2001 seasons where he passed for 7,816 yards with 63 combined touchdowns and another nine scores rushing.

His numbers took a dive in 2003 but the Browns (it was the Browns) decided to pay him $25 million over four years to be their quarterback. It didn’t pay off. Garcia lost seven of his only 10 games with them, passing for a paltry 1,731 yards with 10 touchdowns and nine picks. He moved on to Detroit the next year and played for Philadelphia and Tampa Bay to end his career. He could never find the early-career success he had for the ‘Niners, however.

Photo by Brian Bahr/Getty Images

8. Daryl Gardener, Denver Broncos (2003):

Simply put, Gardener exhibited the traits and talent of an elite NFL defensive tackle throughout the first seven years of his career with Miami and Washington. His size was a fearsome task for opposing offensive linemen.

However, things took a turn for the strange when he was signed to a seven-year, $35 million contract in 2003. The fact he had five tackles in five games for the Broncos was bad enough. But add in the fact he supposedly removed himself from games and reportedly had multiple incidents with teammates, and Gardener’s goose was cooked. He never played another season in the NFL after 2003.

7. Andre Rison, Cleveland Browns (1995):

Rison tore up the stat sheet in his early-career years with the Atlanta Falcons, making him a prized free agent after the 1994 year. He also crossed over into the mainstream when his girlfriend, Lisa “Left Eye” Lopes of the band TLC, burned down his house in 1994.

But his free agent journey to the Cleveland Browns may have gone up in flames even faster. In 1995, he was signed to a five-year deal worth $17.078 million. Yet Rison only lasted one, publicly hating on the Browns’ loyal fans. Rison caught only 47 passes for 71 yards and three touchdowns, all career lows after he had made the Pro Bowl the six prior seasons.

The team moved to Baltimore and became the Ravens the following year. Rison bounced around to several teams but could never regain his early-career success.

6. DeMarco Murray, Philadelphia Eagles (2015):

Murray took the NFL by storm in the 2014 season, rushing an unreal 392 times for a league-leading 1,845 yards and 13 touchdowns. The performance saw him signed to Dallas’ divisional rival Philadelphia the following year. He was supposed to take offensive guru Chip Kelly’s attack to the next level for the Eagles.

Instead, he failed to even come close to living up to his five-year, $42 million contract. He rushed 193 times for 702 yards and six touchdowns in his only year with the Eagles. Murray was traded to Tennessee the following year and then retired after the 2017 season.

5. Deion Sanders, Washington Redskins (2000):

Make no mistake about it, Sanders is arguably the best cornerback in NFL history. But his free agent deal with the Washington Redskins is still one of the worst decisions in NFL history.

Following an illustrious career with Atlanta, San Francisco, and Dallas, “Primetime” signed a ridiculous seven-year, $56 deal with the splurging Redskins in 2000. He rewarded them with 38 tackles, four picks, and a forced fumble and then retired after the end of the year. He would resurface with the Baltimore Ravens years later. Despite his status as a true NFL legend, his short, disastrous tenure in Washington will remain anything besides legendary.

AP Photo/Gerald Herbert

4. Sam Bradford, Arizona Cardinals (2018):

Just like Bradford is one of the biggest draft busts ever due to his overall status and track record, the Oklahoma product is also one of the worst free agent signings ever. He showed flashes in Minnesota but was ultimately unable to stay on the field, a growing occurrence for him.

Despite that, the Cardinals lavished a potential two-year deal worth up to $20 million on the oft-injured name. Three miserable starts under doomed head coach Steve Wilks and he was released. Bradford has yet to resurface.

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3. Kirk Cousins, Minnesota Vikings (2018):

Following a strange run in Washington where he was given the franchise tag on more than one occasion, Cousins signed with the Vikings in 2018. His numbers were decent enough, as he passed for 4,298 yards, 30 touchdowns, and 10 interceptions.

Yet those numbers are deceiving. The sheer number of Cousin’s contract is not, however, as the fact his deal was guaranteed for three years at $84 million, a rate of $28 million guaranteed per year.

So while his numbers are solid enough, the fact that the Vikings badly regressed by going 8-8 and missing the playoffs in Cousin’s first year makes him one of the biggest free agent busts ever thus far. Minnesota went 13-3 in 2017 and was supposed to make the leap to Super Bowl contender status last year. Instead, Cousins often looked confused as he was bombarded behind a suspect offensive line. We’ll see if that changes this year, but for now, he’s a massive free agent bust because his deal is fully guaranteed.

2. Brock Osweiler, Houston Texans (2016):

Osweiler had some solid wins filling in for a quickly fading Peyton Manning in the 2015 season. Denver won the Super Bowl with Manning at the lead that year and offered Osweiler a deal when the legend retired before the next season. The Texans swooped in with a much more lucrative deal, however, flaunting four years at $72 million with $37 million guaranteed for the mainly unproven passer.

He took it and proceeded to pass for 2,957 yards, 15 touchdowns, and 16 interceptions for the Texans in 2016. The Texans made the playoffs in spite of his laughable numbers. He was traded to the Cleveland Browns after one year in one of the strangest salary dump moves in NFL history. Cleveland released him before the season. Osweiler was a backup for the Miami Dolphins in 2018 and is now a free agent. His contract with Houston will always remain at the top of the list in terms of worst free agent signings.

1. Albert Haynesworth, Washington Redskins (2009):

Like Ryan Leaf being ranked at the top of our list of the 32 biggest NFL draft busts, there’s just no other player who could top the worst free agent signings in NFL history.

Haynesworth was always known as a dirty player in the NFL, but was also a dominant force along the defensive line. He was an All-Pro for the Titans in 2007 and 2008. Despite his obvious red flags on the field, that performance earned him a massive seven-year, $100 million deal including $41 million guaranteed with the Redskins after the 2008 season.

Haynesworth made headlines from the get-go in Washington, clashing with head coach Mike Shanahan. He was put through an embarrassing conditioning test to begin training camp his first year with the Redskins. He often clashed with the defensive coaches in Washington due to his dislike of their chosen schemes. Despite all of the drama, he only played 20 games for the Redskins and had 6.5 sacks.

He played 13 more games for the New England Patriots and Tampa Bay Buccaneers and was out of the NFL in early 2012. Haynesworth is and could remain the biggest free agent bust of all-time by a wide margin.