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The NFL free-agent market is a high-stakes game. Get it right and teams can possibly win a championship. Get it wrong and an organization could be set back for several years.
For every free agent gem that proves their worth, there are also horror stories of players who crumbled under the weight of astronomical contracts and lofty expectations. From overhyped quarterbacks to injury-prone superstars, we'll uncover 10 NFL free agents who left a trail of disappointment and regret in their wake.
In this article, we delve into the depths of NFL history to uncover some of the most notorious and regrettable free agent signings ever made, serving as reminders that any franchise can fall victim to the pitfalls of bad personnel decisions.
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#10. Neil O'Donnell, New York Jets
Sometimes things simply come down to timing, and a common theme we'll see on this list is players hitting free agency right after a career-best year or deep postseason run, which often creates recency bias and blinds potential suitors.
Quarterback Neil O'Donnell had several successful seasons for the Pittsburgh Steelers, but it just so happened that he led the Steelers to Super Bowl XXX in his last season under contract with the organization. O'Donnell certainly cashed in nicely on his prior success in Pittsburgh, signing a whopping five-year, $25 million deal with the New York Jets in a signing that was the largest free-agent contract in Jets history at the time.
Unfortunately for Gang Green, O'Donnell's signing did nothing to help the struggling franchise. In his first season as a Jet, he started just six games due to injury and New York finished the year at 1-15...the worst record in franchise history. Things didn't get much better for the O'Donnell-Jets marriage in his second year with the team, as the QB clashed with new Jets head coach Bill Parcells and was ultimately benched in favor of a backup named Glenn Foley. O'Donnell was released following his second season with the squad and left the Jets with an 8-12 record as the team's starting quarterback.
#9. David Boston, San Diego Chargers
After an All-American collegiate career at Ohio State and a successful first four years in the NFL with the Arizona Cardinals that included a Pro-Bowl selection (back when that meant something) and First-Team All-Pro honors, there was little reason to believe that wide receiver David Boston would be one of the worst free agent signings of all time.
However, after signing a massive seven-year, $47.4 million contract with the then-San Diego Chargers in 2003, Boston's NFL career spiraled downward with head-spinning quickness.
Boston played just 14 games across one season for the Chargers, a stint that included a one-game suspension for conduct detrimental to the team. San Diego dealt Boston to Miami just one year into his contract and after missing the 2004 season with a knee injury, he would play just five more games in an NFL career that shockingly ended before he turned 28.
#8. Deion Sanders, Washington Redskins
Unfortunately for Washington football fans, their beloved team is a frequent flyer on this list, as the organization has made numerous boneheaded decisions in the free agency market over the past two-plus decades. One of Washington's most prominent mistakes was handing 33-year-old Deion Sanders a huge seven-year contract worth $56 million in 2000.
Now, there's little debate that Sanders is one of the greatest cornerbacks to ever play the game, as well as one of the most electrifying return men in history. However, "Prime Time" was well past his prime when Washington inked him to a contract that would have tied him to the team until he was 40 years old.
To his credit, Sanders elected to retire from football after just one very disappointing season in Washington rather than try to play out the remainder of his contract. Though he would make a comeback with the Baltimore Ravens four years later, Sanders' huge payday and lone campaign in Washington signaled an end to his ability to compete at a superstar level.
#7. Brock Osweiler, Houston Texans
Apparently, the Houston Texans thought they'd seen enough in Brock Osweiler's seven career starts with the Denver Broncos to sign the unproven quarterback to an eye-opening four-year, $72 million contract in the 2016 offseason. They should have done better scouting.
The unproven Osweiler looked like a potential superstar while going 5-2 down the stretch at the helm for the Broncos in 2015, but the ink was hardly dry on his gigantic new deal with the Texans before the Cinderella-like Osweiler turned back into a pumpkin. The towering QB threw more picks than TDs in his lone season in Houston while averaging less than 200 yards passing per game across his 14 starts.
Osweiler was so bad in his first - and only - season with the team, that the Texans actually paid the Cleveland Browns a second-round draft pick in order to move on from their huge free-agency blunder rather than give the "Wizard of Os" a second year at the helm in Houston.
#6. Le'Veon Bell, New York Jets
Le'Veon Bell's story serves as a cautionary tale to NFL front offices...don't give huge money to a veteran running back in free agency. After appearing on a Hall of Fame trajectory across the first five years of his NFL career with the Pittsburgh Steelers, a bitter contract dispute led Bell to sit out the 2018 season. After becoming a free agent ahead of the 2019 NFL campaign, Bell inked a four-year, $52 million mega-deal with the New York Jets in a contract that made the Michigan St. alum the league's second-highest-paid running back and included $35 million in guaranteed money.
Unfortunately, for both Bell and the Jets, the once-dynamic dual-threat back was never the same after sitting out the 2018 season. The former Steeler struggled to a career-worst season during his first year in NY head coach Adam Gase's offense and appeared noticeably slower while wearing green than he was when donning the black and gold.
Bell's second season in the Big Apple was also in rocky shape before his criticism of the Jets coaching staff led to him being released in October after New York failed to find a willing trade partner. Bell knocked around with multiple teams between 2020 and 2021, but failed to latch on as a solid contributor anywhere and never again looked to be the player he once was.
#5. Adam Archuleta, Washington Redskins
Poor Washington...this marks their second appearance (though sadly, not their last) on this not-top-10 list, and this one is a legitimate head-scratcher. While safety Adam Archuleta had put together an unquestionably rock-solid career with the St. Louis Rams during his first five years in the NFL, he was far from what most would consider a superstar.
Apparently, the decision-makers in Washington felt differently about Archuleta, as the team signed him to a jaw-dropping six-year, $30 million contract in 2006. The free agency windfall made Archuleta the highest-paid safety in NFL history at the time and left many around the league trying to figure it all out.
In true Washington tradition, the signing was an unmitigated disaster, with Archuleta making just seven starts in his lone season with the organization before being benched due to his ineffectiveness in the secondary. Realizing their massive mistake, Washington dealt the embattled safety to the Chicago Bears for just a sixth-round pick ahead of the 2007 season, which would turn out to be Archuleta's last year in the NFL.
#4. Nnamdi Asomugha, Philadelphia Eagles
Even with the benefit of hindsight, it's tough to fault the Philadelphia Eagles too much for targeting Nnamdi Asomugha in the 2011 offseason. A defensive star, Asomugha was coming off three straight Pro Bowl seasons with the Oakland Raiders and was roundly considered to be the top free agent in the NFL at the time.
However, things never worked for the coveted defensive back in Philly, as Asomugha struggled to adapt to the Eagles' zone-heavy defensive scheme while never flashing the skills and speed that he'd so consistently exhibited with the Raiders.
While there was hope that Asomugha would assimilate and improve during in his second season as an Eagle, he continued to struggle in the City of Brotherly Love, and he was released after playing just two seasons of the five-year, $60 million contract he'd signed in free agency. Asomugha spent the 2013 campaign with the San Francisco 49ers and was out of football altogether just a year later.
#3. DeMarco Murray, Philadelphia Eagles
What have we learned today, kids? Be wary of veteran running backs in the free-agent market. The Eagles were eager to land the NFL's 2014 Offensive Player of the Year, DeMarco Murray, ahead of the 2015 campaign. Murray was coming off a massive season with the Dallas Cowboys in which he'd lead the NFL in rushing with a ridiculous 1,845 yards.
Perhaps Dallas' refusal to meet Murray's contract demands should have been a red flag for the Eagles, yet they still pulled the trigger on a huge five-year, $42 million deal for the then 27-year-old back. Philly's master plan was to form a 1-2 punch in their new-look backfield by pairing Murray with fellow free-agent signee Ryan Mathews in 2015.
However, the arrangement fizzled, as the Birds slumped to a 7-9 record. After rushing for over 1,800 yards behind an excellent offensive line during his last year in Dallas, Murray's production nosedived dramatically in Philly, as he eeked out just over 700 yards with the Eagles in 2015. The organization decided to cut its losses and promptly shipped Murray to the Tennessee Titans for next to nothing before he could play a second season in Philadelphia.
#2. Kenny Golladay, New York Giants
Kenny Golladay wasn't considered a superstar when he hit free agency ahead of the 2021 NFL season, but the New York Giants paid him like one anyway, handing Golladay a juicy four-year, $72 million contract. Sure, he'd had some nice seasons with the Detroit Lions, crossing 1,000 yards receiving in 2018, while again going over 1,000 yards in 2019 en route to leading the NFL with 11 receiving TDs and being named to the Pro Bowl.
Despite those successful campaigns, Golladay was coming off a 2020 season in which he played in just five games for the Lions due to a season-ending hip flexor injury. That didn't stop then-Giants GM Dave Gettleman from backing up the Brinks truck for Golladay and handing the receiver that had started every game of a season just once in his four-year career a contract with $40 million guaranteed.
Golladay's time in the Big Apple was a hot mess from the get-go, as he reeled in just 37 receptions in his first season with the G-Men in 2021. Things somehow got even worse in 2022, as the free-agent bust started only four games for Big Blue and logged a grand total of six catches for 81 yards. The Giants officially released Golladay following the 2022 season. His two years in New York ended with him starting 18 games and totaling a laughable 43 catches for 602 yards with just a single touchdown.
#1. Albert Haynesworth, Washington Redskins
Ah yes, the veritable gold standard in disastrous free-agent signings. Washington's eye-popping seven-year, $100 million dollar commitment to Albert Haynesworth still serves as an NFL cautionary tale of how bad free agency can go.
After a monster 2008 campaign with the Tennessee Titans in which Haynesworth earned NFL All-Pro honors for the second consecutive year, the big defensive lineman was a hot item in the free-agent market. Washington "won" the rights to Haynesworth's services by giving him the biggest contract ever for a defensive player in the spring of 2009. The organization thought they were getting Reggie White 2.0, instead, they got a player that was out of shape, unmotivated, and a problem in the locker room.
Haynesworth registered just four sacks in 12 games during his first season with the team in 2009 and was ultimately suspended by Washington head coach Mike Shanahan after eight ineffective appearances in 2010. After two years with the organization - and some of the laziest on-field plays in NFL history - the disappointing Haynesworth was shipped to the New England Patriots for a fifth-round pick in the 2011 NFL draft.
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