NFL Free Agency can be an extremely valuable tool in building an elite roster. It can also serve as a cautionary tale for the greedy, get-rich-quick types of general managers. Some teams have been burned more than others in NFL free agency, but certain free agent signings in the last 30 or so years as the NFL has started giving out absolutely massive deals have been brutal.
More brutal than the rest.
What are the top 15 worst NFL free agent signings of all time?
15 worst NFL free agent signings in history
15. Case Keenum, QB, Denver Broncos
The deal: 2 years, $36 million
Some of the moves on this list may not be on everyone’s list, but this is my list, and it’s hard to ignore how bad this move was by the Denver Broncos given the context of their situation. The Broncos had a top-five pick in the 2018 NFL Draft (5th overall). Their coaching staff, at the time, was tasked with coaching one of the rosters at the Senior Bowl, and they were gifted the opportunity to coach Baker Mayfield and Josh Allen the entire week.
Despite the up-close look at both Mayfield and Allen for a full week, the Broncos passed on drafting any quarterbacks at all. They didn’t make an aggressive enough push at Kirk Cousins (that we know of) in free agency and decided instead to go after Case Keenum of the Minnesota Vikings, fresh off the Minneapolis Miracle.
Keenum had a good season for the Vikings in 2017 in relief of Sam Bradford. Perhaps more important to the Broncos was Keenum’s connection to Gary Kubiak and Vance Joseph from their days together in Houston. Familiarity and connections are always key factors in free agency, sometimes to a fault.
The Broncos gave Keenum just a two-year deal, but it was a crippling move. They paid him starter money with $25 million guaranteed at signing. Keenum started just one season for the Broncos who finished as one of the 10 worst teams in the league in 2018. They traded him the following offseason to Washington and even with Russell Wilson on the roster today, the Broncos are still searching for the answer at QB.
14. Ahman Green, Houston Texans
The deal: 4 years, $23 million
From 2000-2006, Ahman Green was one of the best running backs in the NFL as a member of the Green Bay Packers. Outside of the 2005 season when he only played five games, Green was pretty much an automatic 1,000 yards rushing and provided plenty of added value in the passing game as a receiver.
Green was named to multiple Pro Bowls and All-Pro teams as a member of the Packers, which prompted the Houston Texans to sign him to a four-year deal worth $23 million in the 2007 offseason. Former Packers coach Mike Sherman was part of Gary Kubiak’s staff in the early years of Kubiak’s tenure with the Texans, and he helped convince Kubiak and the Houston front office to not only bring in Ahman Green but another former Packers running back — Samkon Gado — to really provide a jolt to the Houston running game.
As fate would have it for Houston that season, it actually ended up being Ron Dayne having the most significant impact on the running game, leading the team in rushing while Green played in just six games.
By 2008, Steve Slaton had taken over the show for the Houston running game and Green — once again playing in just eight games — took a major backseat.
After racking up nearly 11,000 yards from scrimmage with the Packers from 2000-2006, Green became less than a role player in Houston. He played just 14 games for the Texans with just six starts.
As it turns out, giving a 30-year-old free agent running back a $23 million contract may not be the best idea.
13. Jeff Garcia, QB, Cleveland Browns
The deal: 4 years, $25 million
Jeff Garcia had a cool factor about him as a member of the San Francisco 49ers in the early 2000s. Garcia, to his credit, is one of the most decorated professional football players of all time. His career just wasn’t always in the NFL.
Actually, Garcia was a four-time All-Star in the Canadian Football League before he started any NFL games at the age of 29. When he got to the NFL, he wasted little time making a major impact on the 49ers’ offense.
Back when the NFL was still very much a league dominated by running backs, Garcia became one of a very slight few quarterbacks to have back-to-back seasons with more than 30 touchdown passes (2000, 2001). He went from being a Grey Cup MVP and on top of the CFL to almost immediately becoming a household name in the NFL.
He spent five years with the 49ers organization, the meat of which was rather successful. In his fifth season, however, at the age of 33, the 49ers were just 7-9 and decided to make changes. Garcia hit free agency and wound up signing with the Cleveland Browns to a four-year deal worth $25 million.
Injuries limited Garcia to just 11 games and 10 starts as a member of the Browns where he completed only 57.1 percent of his passes, the worst of his NFL career. His 3.6 interception rate was the highest of any of his stops in the NFL as well.
His time with the Browns lasted just one year before he signed in Detroit the following offseason. After being benched in Detroit, Garcia once again changed teams the next year and went to play for Andy Reid in Philadelphia. As was the case for many QBs under Reid, Garcia shined.
He was in the running for comeback player of the year after Donovan McNabb went down with a season-ending injury, forcing Garcia into the lineup. He parlayed his backup work in Philadelphia into the full-time starting role with the Bucs the next year, where he made the Pro Bowl.
12. Neil O’Donnell, QB, New York Jets
The deal: 5 years, $24 million
Neil O’Donnell was a third-round pick by the Pittsburgh Steelers in 1991 and wound up the full-time starter by his second season in the league. He was named to the Pro Bowl in 1992 and helped get the Steelers to Super Bowl XXX in the 1995 season. O’Donnell had a clutch factor to him, leading the Steelers on 14 game-winning drives in his first five NFL seasons.
After the Steelers’ loss to the Cowboys in Super Bowl XXX, O’Donnell hit free agency and chose to sign with the New York Jets. Splitting starts with Frank Reich and Glenn Foley, O’Donnell went 0-6 in his first year with the Jets before playing much better in 1997. He started 14 games for the Jets in 1997 and the team had success with him in the lineup, going 8-6. Unfortunately, O’Donnell was sacked a whopping 45 times that season (most in his NFL career) and a contract dispute in 1998 led the Jets to get rid of him.
O’Donnell was obviously supposed to come in and be the franchise QB of the Jets but that never materialized. Perhaps his attitude wasn’t right, perhaps Bill Parcells was a little to quick on the trigger to let him go.
Whatever the case, the Jets were 12-4 in the 1998 season and had the fifth-best offense in the NFL with Vinny Testaverde under center.
O’Donnell went to the Bengals on another pretty lucrative free agent deal after that, only to play one season there before becoming a longtime backup in Tennessee from 1999-2003.
11. Adam Archuleta, S, Washington
The deal: 6 years, $30 million
Believe it or not, Adam Archuleta isn’t just one of the top color commentators for the NFL on CBS. He was once a coveted NFL prospect, first-round pick, and big-time free agent acquisition of the Washington franchise.
In the 2001 NFL Draft, the St. Louis Rams took Archuleta with the 20th overall pick out of Arizona State. He played with the Rams for five years where he was a tackling machine, causing turnovers, attacking the line of scrimmage, and impacting the Rams’ defense.
After the 2005 season, Archuleta hit free agency where Washington gave him $30 million on a six-year deal. At that point in NFL history, that was the richest deal for a safety ever. Archuleta was joining a team known for giving out big money in free agency on an annual basis, and he didn’t even end up starting all of the 16 games he played for them.
As good as Archuleta was at attacking the line of scrimmage, Washington couldn’t count on him in coverage and he was effectively benched. He was let go after just one season with Washington, he was traded to the Chicago Bears and lasted there just one more season.
The former first-round pick got a shot to make it as a linebacker with the Raiders in 2008 but it didn’t work out. He became a father that year and started a family, got married in 2010, and has become one of the best color commentators in the business as of 2023 along with play-by-play man Greg Gumbel.
10. David Boston, WR, San Diego Chargers
The deal: 7 years, $47.4 million
There are few NFL players in history that look better in their uniform than David Boston. In terms of the bodybuilding aesthetic, this guy was certainly one of the first players you want “coming off the bus” for your team. David Boston was tremendous for the Arizona Cardinals in 2000 and 2001, averaging nearly 100 yards per game in the 2001 season with first-team All-Pro honors and a Pro Bowl nod.
In 2002, Boston ended up playing just eight games but it didn’t hurt him much in 2003 NFL free agency, where he signed a now-infamous seven-year deal worth $47.4 million in total money with the San Diego Chargers.
The Chargers, at the time, had the young nucleus of third-year players Drew Brees and LaDainian Tomlinson. What a time, right?
Boston played pretty well for the Chargers in the 2003 season, catching 70 passes for 880 yards and seven touchdowns. Still, there was some trouble in paradise as Boston’s attitude did not fly with head coach Marty Schottenheimer or GM AJ Smith. The team suspended him for a game in 2003 due to Boston cussing out the Chargers’ strength coach.
He missed the entire 2004 season due to a knee injury, but not before he was suspended four games for steroids.
After that 2004 season, the Chargers got tired of Boston’s approach to work and traded him to the Miami Dolphins where he played just five games before suffering another major injury. He got another shot in Tampa Bay but it didn’t amount to anything.
9. Deion Sanders, CB, Washington
The deal: 7 years, $56.125 million
You know a free agent signing is bad when you’re talking about one of the top superstars to ever play the game, and you come across a move like this and you think to yourself, oh wow, he played for Washington?
That was my thought process regarding Deion Sanders, “Coach Prime”, one of the most popular football figures in the country right now. Growing up as a 90s kid, Prime was it. If you didn’t have a Deion Sanders jersey, you certainly wore a bandanna when you played backyard football and did his trademark high-stepping into the end zone on a pick-six. There was nothing more satisfying.
Deion Sanders is synonymous with the no. 21. I remember clearly his time as a member of the Falcons, Cowboys, and 49ers. He was so much fun to watch.
Why can I not remember his time with Washington?
It wasn’t like Sanders was “bad” for Washington. He picked off four passes for them and then shockingly retired after the 2000 season. Sanders would have been entering his age 34 season, so it’s not altogether surprising given his age, but the timing given the fact he signed a seven-year deal with Washington was certainly out of left field.
After his retirement, Prime attempted to come back and play for the Raiders, and even though Washington was shockingly willing to accommodate his request, the Chargers sniped him off waivers and it ended up being too late in the season for him to be activated. He came back and played two years for the Baltimore Ravens in 2004-05 before getting into TV and now, of course, coaching.
8. Nnamdi Asomugha, CB, Philadelphia Eagles
The deal: 5 years, $60 million
The Philadelphia Eagles dream team, as dubbed by former quarterback Vince Young, turned out to be a bit of a nightmare.
Don’t get it twisted, though. From 2003-2010, Nnamdi Asomugha was one of the best defensive backs in the NFL, earning All-Pro recognition just the year before he ended up signing the lucrative five-year, $60 million deal with Philadelphia.
Signing with Philadelphia also marked the beginning of the end of Asomugha’s best days as a pro. He picked off three passes in his first year with Philly, but played poorly enough in 2012 that the Eagles decided to cut him after not being able to restructure his deal.
In the grand scheme of things, it probably wasn’t a bad process for the Eagles to sign Asomugha and be as aggressive as they were in doing so, but this was a player who walked from the Raiders after an All-Pro campaign. Teams weren’t throwing much at Asomugha in Oakland because this guy had a 6-foot-3 frame and tremendous ball skills. He was named first-team All-Pro with 0 interceptions, 6 passes defensed, and only 19 total tackles.
How does that happen?
The Eagles were suckered into paying big-time money for a 30-year-old cornerback is what it was. We all know that NFL contracts may look big on paper but in reality, they are mostly 2-3 year pacts with players that don’t affect the team too much beyond those first couple of years because they’re not fully guaranteed.
Asomugha’s big contract with the Eagles was warranted at the time but looks horrendous in hindsight because he didn’t have any longevity there and the “dream team” only won 12 games in two seasons while he was there.
7. Ja’Wuan James, OT, Denver Broncos
The deal: 4 years, $51 million
The saga between the Denver Broncos and Ja’Wuan James has been a pretty wild one. James was given the richest deal for a right tackle in NFL history by the Denver Broncos in the 2019 NFL offseason, and he was their prized free agent pickup that offseason among a number of significant moves.
The Broncos have had a revolving door at right tackle and a number of really bad free agent signings at the position since the team won Super Bowl 50, and quite frankly they are still looking for a long-term solution at the right tackle position today.
They certainly thought James would be the guy.
They gave James $32 million in total guaranteed money on this contract, but the first game into his Denver Broncos career, he got hit in the knee by Raiders linebacker Vontaze Burfict and only saw the field for three total games while recovering from the knee injury. He was medically cleared to play by the Broncos but James didn’t feel comfortable playing on the knee, so he sat all but three games.
In the 2020 offseason, James was one of the players who decided to opt out of the season due to the pandemic, so his contract tolled to 2021. The Broncos were hoping James could be part of the solution for their offensive line yet again in 2021, but when the NFLPA encouraged players not to work out at team facilities due to the ongoing CBA negotiations, James left the Broncos facility where he was working out and suffered an Achilles injury off-site.
Because it was off-site, he lost all of the remaining guarantees on his contract, approximately $15 million total. He filed a grievance but only settled at $1.09 million.
Essentially, the Denver Broncos wasted three years at the right tackle position banking on Ja’Wuan James. James got a bunch of money from the Broncos up front but really never saw the field. In terms of millions of dollars being played over games played? James might be the worst free agent signing in NFL history based solely on that. $17 million for three games in Denver.
6. Michael Vick, QB, Philadelphia Eagles
The deal: Does anyone actually know?
The Michael Vick contract with the Philadelphia Eagles has been labeled a six-year deal worth $100 million, a five-year deal worth $80 million, a longer deal worth $140 million.
The reality is, the Eagles ended up paying Vick a grand total of $44.7 million from 2011-2013. When Vick came back from his suspension, he signed with the Eagles as a backup in 2009. That deal he signed in 2009 ended up being one of the better bargains the Eagles would make. After serving a year as the backup in Philadelphia, Vick would win NFL Comeback Player of the Year in 2010 as well as earn a Pro Bowl nod.
In 2011, he signed the deal that is reported as being $80 million over five years, but his play never came close to matching what the Eagles got in 2010.
Vick’s numbers trended downward in 2011 and 2012, and the Eagles fired Andy Reid after the 2012 season. He ended up getting hired by Kansas City, and we all have seen how that’s turned out.
Vick was with the Eagles again in 2013 before stints briefly with the Jets and Steelers.
It’s hard to blame the Eagles for making the massive deal they did with Vick after the 2010 season. Vick was out of football from 2007-08 so the Eagles probably assumed he had plenty of tread left on the tires. Unfortunately, if their assumptions about Vick led to the eventual dismissal of Andy Reid? That’s not great.
5. DeMarco Murray, RB, Philadelphia Eagles
The deal: 5 years, $40 million
NFL running backs in today’s game are probably trying to figure out what they have to do to get teams to pay their position what they were paying DeMarco Murray just a few years ago.
The former Dallas Cowboys star signed with a division rival after the 2014 season in which he racked up over 2,200 yards from scrimmage, finished third in MVP voting, first-team All-Pro, and 13 total touchdowns on almost 450 touches.
The Eagles gave Murray a boatload of money and he barely cracked 1,000 yards from scrimmage with seven total touchdowns. The Eagles, as a team, went 7-9 during the season and ended up firing head coach Chip Kelly.
The move turned out to be even more brutal for Philadelphia because they decided to move on from Murray just one year into the deal. Murray was traded to the Titans in the 2016 offseason in exchange of fourth-round picks, and the Eagles basically decided to just dump him.
He actually went on to have a really good 2016 season for the Titans, racking up over 1,600 yards from scrimmage with 12 touchdowns on the way to another Pro Bowl nod. He played one more season for the Titans before his NFL career ultimately ended.
4. Javon Walker, WR, Oakland Raiders
The deal: 6 years, $55 million
Javon Walker was a first-round pick of the Green Bay Packers in the 2002 NFL Draft. He played for the Packers for four seasons before being traded to the Denver Broncos during the 2006 NFL Draft for a high second-round pick. Walker was traded after playing just one game in the 2005 season and entering the final year of his rookie deal.
After being traded to the Denver Broncos, Walker became a household name again during the 2006 season. He was one of the favorite targets of Jake Plummer and had over 1,200 yards from scrimmage with nine total touchdowns (8 receiving, 1 rushing).
Then, tragedy struck.
Just hours into the new year in 2007, Walker’s teammate with the Denver Broncos — Darrent Williams — was killed in a fatal shooting. Walker was not only in the vehicle, but Williams died in his arms, according to Walker’s account. That event undoubtedly took its toll on Walker mentally, physically, and emotionally. It probably goes without saying that playing in Denver after that was hard for him. He ended up only playing eight games in the 2007 season and his productivity dropped off considerably.
The Broncos tried to trade walker in the 2008 offseason, but not successfully. He ended up getting released and signing with the Raiders on a pretty massive six-year deal worth $55 million, $21 million over the first two years.
Walker would go on to play just 11 total games for the Raiders, catching just one touchdown pass.
3. Brock Osweiler, QB, Houston Texans
The deal: 4 years, $72 million
The Denver Broncos won Super Bowl 50 thanks to their tremendous defense, but anyone who followed that team closely knows that they wouldn’t have likely gotten where they did if it wasn’t for the play of backup quarterback Brock Osweiler. Although he wasn’t perfect, Osweiler was exactly what the Broncos needed in place of a very clearly injured Peyton Manning, who looked like he was on borrowed time as of the 2015 season.
Osweiler played well for the Broncos, making some clutch throws in some massive wins as the team earned its way to the no. 1 seed in the AFC. Unfortunately for Osweiler, he would be benched in the regular season finale for a healthy enough Manning, and Manning took over the show in the postseason.
That benching certainly rubbed Osweiler wrong, especially after he’d already sat behind Manning from 2012-on.
After the Broncos won Super Bowl 50, Osweiler was offered a deal to remain the team’s starter. He passed it up, hit free agency, and signed a four-year deal with the Texans without ever visiting the team. That’s not totally uncommon in free agency, but when you’re talking about quarterbacks, it’s probably not a bad idea to sit everyone down and see if it might be a fit.
Osweiler signed the deal, spurning the Broncos in the process, and became Houston’s starter. How did it go?
It went poorly enough that the Texans would end up paying the Cleveland Browns a second-round draft pick just to eat some of Osweiler’s remaining money. He spent just one dismal season in Houston, and actually ended up getting re-signed by the Broncos in 2017 for a bit, starting four games.
2. Le’Veon Bell, RB, New York Jets
The deal: 4 years, $52.5 million
Running backs nowadays are probably trying to figure out how they can order whatever Le’Veon Bell was having just a handful of years ago. The running back position has depreciated so much in value in today’s NFL, even since Bell signed this deal with the Jets, that the franchise tag is barely over $10 million. Teams simply don’t pay running backs $13 million per year anymore.
Le’Veon’ Bell’s free agency story is one of the wildest in recent NFL history, no question about it.
After some really great years with the Pittsburgh Steelers, Bell was slated to finally hit free agency in the 2018 offseason. The Steelers ran this man into the ground. They gave him 1,541 touches in five seasons, an average of over 300 per year.
In 2018, Bell wasn’t about to play on the franchise tag again. He could have played for $14.5 million totally guaranteed from the Steelers, but instead, he decided to make a point and sit out the season. After holding out the entire 2018 season, the Steelers let him walk in 2019 free agency and Bell got his bag.
He signed with the Jets to the aforementioned four-year deal worth over $13 million per season. He got a whopping $35 million in guaranteed money. The Jets probably figured that Bell, even though he was already 27, had at least three great years left as one of the best dual-threat running backs in the NFL. They were wrong.
Bell was force-fed his 300-plus touches in 2019 but was not nearly as effective for the Jets as he once was for the Steelers. He played two games for the Jets in 2020 before he was let go and started bouncing around the league.
The Jets got 1,363 yards from scrimmage and four total touchdowns out of Bell for $35 million guaranteed.
1. Albert Haynesworth, DL, Washington
The deal: 7 years, $100 million
Albert Haynesworth’s free agency story is almost a legend at this point. It’s almost poetic that it happened to be Washington that actually signed him, but it could have really been anybody as it was rumored that a third of the league or more was blowing up Haynesworth’s phone at the start of free agency.
Everyone wanted a piece of this guy. Why?
The 6-foot-6, 335-pound Haynesworth was causing absolute havoc as an interior player on the Tennessee Titans defense in 2007 and 2008. He was a first-team All-Pro both seasons, he was getting Defensive MVP votes, and he was only going to be 28 years old going into 2009 NFL free agency.
Washington ended up winning the bidding war for his services, paying him the first $100 million contract for a defensive player in league history, if I recall correctly. At the time, there were only a small handful of $100 million deals signed in league history overall, most of them were 10-year contracts or longer.
For Haynesworth, it was history made. Washington fell into their usual NFL free agency trap and Haynesworth was a horrible bust for the franchise despite apparently taking “less” money to play there than he could have gotten in Tampa Bay. For $41 million in guaranteed cash, Haynesworth played just 20 games for Washington before falling out of favor with multiple different coaching staffs.
He was later traded to the Patriots for a draft pick but only played six games there. He finally got the chance to go to Tampa Bay in 2011 where he played seven games, but the Bucs cut him the following offseason and Haynesworth never played again.
Nobody could have known in 2009 when that seven-year deal was signed that the 28-year-old Haynesworth would be done playing in basically the next two years. Plenty of shocking contracts have been signed in the NFL and Haynesworth’s is not the absolute worst, but when it comes to expectations of a free agent changing teams, this still remains the greatest cautionary tale of them all.