Each spring, the NFL kicks off its free agency period and has the NFL Draft. Both of those processes often turn NFL players – or soon-to-be-NFL players – into very rich men. In fact, the tens of millions of dollars that many of these players are promised in their contracts are amounts the common person will never see in their lifetime.
But as any NFL fan knows: many of these contracts turn out to be very bad business decisions, when we look back on them in hindsight. Often times, NFL teams simply don’t get the NFL player they hoped they paid for via a lucrative contract deal, leading to a whole lot of “buyer’s remorse.”
To highlight those occurrences, we’ve put together a list of 25 of the worst NFL contracts ever assigned, for your reading pleasure… unless you happen to be a fan of any one of these teams!
David Boston (San Diego Chargers)
In 2003, wide receiver David Boston was an emerging star in the NFL. After recording two straight seasons with over 1,150 yards receiving, Boston was a hot commodity heading into free agency. Which is exactly why the San Diego Chargers signed Boston to a massive seven-year, $47 million contract in 2003. It didn’t take long for things to turn ugly for the Chargers and Boston.
As his physical size increased to alarming proportions, rumors swirled of Boston taking performance enhancing substances. Which would explain his antics in San Diego — including a messy fight with a strength coach, and his generally “moody” demeanor. It was eventually announced that Boston tested positive for substances often used by bodybuilders. The Chargers released Boston after just one forgettable season.
Vernon Gholston (New York Jets)
Even after breaking the single-season sack record during his last year at Ohio State, the idea of Vernon Gholston being taken with a top 10 selection in the 2008 NFL Draft made a lot of NFL scouts rather uncomfortable. But, of course, that didn’t stop the New York Jets from taking him with the 6th overall pick in said draft, and paying him a 5-year, $50 million deal with $21 million guaranteed
Gholston’s career trajectory was symbolized by having has his deal re-negotiated two years later for just $3.45 million annually. Said career lasted 45 games over three seasons, in which he shuffled between end, tackle, and linebacker, recording only 16 tackles in his career — and zero quarterback sacks.
DeMarco Murray (Philadelphia Eagles)
As if we needed further proof that Chip Kelly had no idea what he was doing in the NFL, we need to look no further than the Philadelphia Eagles’ acquisition of DeMarco Murray. Even after signing free agent running back Ryan Mathews, the Eagles still thought it was necessary to give Murray a massive five-year, $40 million contract. Kelly envisioned a backfield where Murray and Mathews would each get double-digit carries, wearing out opposing defenses.
Instead, the only thing Murray ended up “wearing out” in the 2015 season was the bench. He was an awful fit in the Eagles offense, and eventually lost a majority of his carries to Mathews and Darren Sproles. Just one year into his contract, the Eagles traded Murray to the Titans. To make matters worse for the Eagles, Murray had a fantastic bounce back season in 2016 with the Titans.
Jason Smith (St. Louis Rams)
With the second overall pick in the 2009 draft, the then-St. Louis Rams selected tackle Jason Smith. If it’s any consolation to fans of the Rams: the top 10 picks of that Draft turned out to be pretty miserable in hindsight.
But the contract signed by Smith was pretty miserable as well, given the gift of hindsight. The supposed franchise bookend was signed for $61 million over 6 years, including $33 million guaranteed. In three seasons with the Rams, Smith only saw action in 29 of a possible 48 games, with 26 starts. With an injury history and slow adaptation to an NFL-style offense (Smith played at Baylor in college), the Rams traded him after just three seasons of under-performance.
Tyson Jackson (Kansas City Chiefs)
When Scott Pioli came over from New England to become the General Manager of the Kansas City Chiefs, he thought he was out-smarting everyone in the NFL by reaching for Tyson Jackson with the third overall pick in the 2009 NFL Draft. That was followed by Jackson being signed to a five-year, $57 million contract with $31 million guaranteed.
Pioli thought he was getting a player who would be the “Richard Seymour” prototype for the Chiefs. Instead, Jackson played five seasons with the Chiefs but only accrued nine sacks and 137 solo tackles. In other words: he shouldn’t even be mentioned in the same name as Seymour.
Aaron Curry (Seattle Seahawks)
The hits from the 2009 NFL Draft keep on coming. The Seattle Seahawks were lauded for taking the “safe” pick of Aaron Curry at #4 overall. Following that selection, Curry signed a 6-year, $60 million contract with $34 million guaranteed, which at the time was the most money ever given to a non-QB rookie in NFL history.
In 35 games with the Seahawks over 2.25 seasons, Curry had 5.5 sacks and just 163 solo tackles in his four-year career. Those are the types of numbers a top five linebacker should be putting in one year, let alone over multiple seasons.
Darrius Heyward-Bey (Oakland Raiders)
Yep, believe it or not, here’s another one from the 2009 NFL Draft – courtesy of the late Al Davis’ infatuation with speed. With the seventh overall pick, the Oakland Raiders selected Darrius Heyward-Bey in large part to his 4.3 seconds 40-yard-dash at the Combine. That speed earned him a five-year, $38.25 million deal with $23.5 million guaranteed.
Heyward-Bey caught only 140 passes and scored a mere 11 touchdowns during his four seasons with the Raiders. He was released in 2013, and while he resurrected his career in Pittsburgh, he never came close to his top-10 draft billing.
Neil O’Donnell (New York Jets)
Neil O’Donnell earned a fat contract after Super Bowl XXX, despite effectively handing said Super Bowl over to the Dallas Cowboys. But the New York Jets believed that O’Donnell’s miserable performance as the Pittsburgh Steelers’ quarterback in that Super Bowl was an outlier.
The Jets were willing to overlook his Super Bowl meltdown, and rewarded him with a lucrative five-year, $25 million deal. No surprises here, O’Donnell’s deal was a disaster. In his first season in New York, O’Donnell lead the Jets to a franchise worst 1-15 record. He spent most of the following season in Bill Parcells’ doghouse, and was eventually released.
Javon Walker (Oakland Raiders)
Despite having missed at least eight games in two of the past three seasons prior due to knee injuries, the Oakland Raiders ignored those red flags and signed wide receiver Javon Walker to a six-year, $55 million contract in 2008. Things couldn’t have started off worse for Walker, who was beaten and robbed of $100,000 in jewelry, cash and credit cards after a night of partying in Las Vegas, before ever playing a game with the Raiders.
He did manage to play in eight highly uninspiring games that season (recording only 15 catches for 196 yards), before missing the final eight games due to injury. He played in three more games for Oakland in 2009, before the Raiders eventually parted ways with him.
Joey Harrington (Detroit Lions)
After being selected with the third overall pick in the 2002 NFL Draft by the Detroit Lions, quarterback Joey Harrington signed a 6-year, $36.5 million rookie deal with $13 million guaranteed. Nobody really flinched at the deal, even with the amount of money it comprised, because everyone hoped Harrington would resurrect the moribund Lions’ franchise.
Alas, how wrong we all were. Harrington played on awful teams with awful offensive lines, leading to a musical chair of coaches, schemes, and players around him. He compiled a brutal 18-37 record over four years in Detroit. It’s no wonder people questioned his love for the game; you’d stop loving football if you were put in that miserable situation.
Dale Carter (Denver Broncos)
Cornerback Dale Carter spent the first seven years of his career with the Kansas City Chiefs, where he blossomed into one of the best defensive backs in the NFL. When Carter hit the free-agent market in 1999, the Denver Broncos thought it would be a good idea to steal him away from their division rival. Willing to overpay for his services, the Broncos signed Carter to a six-year, $34.8 million contract.
Although Carter provided a respectable effort in the 1999 season, it would be his first and only season in Denver. He was suspended for the entire 2000 season, and half of the 2001 season, for violating the league’s substance abuse policy. After multiple arrests, the Broncos eventually parted ways with Carter.
Aaron Maybin (Buffalo Bills)
The Buffalo Bills selected defensive end Aaron Maybin with the 11th pick in the 2009 draft, after witnessing the fact that Maybin had the body of a Greek god combined with the athleticism of a running back. After being taken with said pick, he was rewarded with a 5-year, $25 million contract including $15 million guaranteed.
In turn, Maybin rewarded the Bills with one forced fumble, 23 tackles, and zero sacks over 27 games. Buffalo released him after two terrible seasons, and he went on to play only 21 more games in his career with the New York Jets. Prior to the start of the 2013 season, Maybin was out of the NFL.
Matt Leinart (Arizona Cardinals)
The tenth overall pick in the 2006 NFL draft, Matt Leinart signed a 6-year, $50.8 million contract with $14 million guaranteed to be the future star quarterback of the Arizona Cardinals. Unfortunately for the Cardinals, Leinart only started 17 games in his four seasons with the team, and spent far too much of his time enjoying his celebrity status, instead of focusing on being a professional quarterback.
Leinart went 7-10 in his 17 starts, completing 57% of his passes with 14 touchdowns and 20 interceptions. After a year each with Houston and Oakland, appearing in just four games, Leinart was out of the NFL.
Jeff George (Washington Redskins)
Quarterback Jeff George was the #1 overall pick in the 1990 NFL draft. After bouncing around the league for the next decade, the Washington Redskins decided George was the missing piece to their puzzle. In 2000, Redskins owner Dan Snyder (foolishly) signed George to a four-year, $18.3 million contract. In his first season with the team, George started only six games and threw seven touchdowns and six interceptions.
The following year he started the first two games of the season and threw three interceptions. Apparently, that was enough evidence for new head coach Marty Schottenheimer, who released George just two weeks into the season. Unfortunately for Redskins fans, Jeff George still isn’t the worst of the many awful (Dan Snyder) signings that will appear on this list.
Dana Stubblefield (Washington Redskins)
Most NFL fans don’t realize that one of Washington’s most colossal free agent failures actually took place before Dan Snyder purchased the team. In 1998, the Redskins signed defensive tackle Dana Stubblefield, the reigning NFL Defensive Player of the Year, to a six-year, $36 million contract.
But Stubblefield was never the same player in Washington. In 1997, his final season with the 49ers, Stubblefield was unstoppable, recording a league high 15 sacks. In his three seasons with the Redskins, Stubblefield totaled just 7 sacks.
Robert Gallery (Oakland Raiders)
When Robert Gallery was selected with the second overall pick in the 2004 NFL Draft by the Oakland Raiders (sandwiched in between the selections of Eli Manning and Larry Fitzgerald), he was considered as safe and “can’t-miss” a player as there was in the Draft.
Alas, how wrong we were. The University of Iowa lineman received a 7-year, $60 million contract with $18.5 million in guaranteed money. He started as a tackle in the NFL, but was moved to guard after 2006 when he played 13 games and still placed fourth in the league for most sacks given up. Gallery was drafted and paid to be a benchmark tackle, not to play guard.
Matt Flynn (Seattle Seahawks)
Two years after the Seattle Seahawks handed Matt Flynn a three-year, $26 million contract, they won the Super Bowl. The sad irony? By that point, Matt Flynn wasn’t even on the team. After capitalizing on garbage time stats as Aaron Rodgers’ replacement in Week 17 of the 2011 season, the Seahawks signed Flynn to be their next starting quarterback.
But, during that same 2012 off-season, the Seahawks happened to draft some guy named Russell Wilson. Ever heard of him? The rookie Wilson outperformed Flynn in training camp, forcing head coach Pete Carroll to name Wilson the starting QB. Wilson did not disappoint, and Flynn never started a game for the Seahawks. He was eventually traded to the Oakland Raiders for a 5th-round draft pick.
Nnamdi Asomugha (Philadelphia Eagles)
In 2011, Pro Bowl cornerback Nnamdi Asomugha left the Oakland Raiders to sign a five-year, $60 million contract with the Eagles. The deal made him the highest paid corner in the NFL. But the honeymoon was short lived, as Asomugha showed serious signs of decline from the get-go in Philadelphia.
During his first two seasons, Asomugha and his enormous contract were picked apart, as the Eagles allowed a whopping 60 touchdown passes. When Asomugha refused to renegotiate his contract after the 2012 season, the Eagles parted ways with him.
Brock Osweiler (Houston Texans)
To say that the Brock Osweiler experiment in Houston was an utter and complete disaster would still be quite the understatement. After signing a four-year deal worth a whopping $72 million, Osweiler did very little to deserve a single dollar of that money last season. In 15 games, Osweiler threw just 15 touchdowns compared to 16 interceptions.
During his one season in Houston, Osweiler was widely inaccurate and his decision-making was atrocious. In a not so surprising move, the Texans traded Osweiler, his massive salary, and valuable draft picks to the Cleveland Browns. That’s right; the Texans actually traded away draft picks to Cleveland, along with Osweiler, just to get his hideous contract off their salary cap.
Deion Sanders (Washington Redskins)
During the 1990’s, cornerback Deion Sanders was the most electrifying player in the NFL. Whether he was shutting down opposing receivers with his elite coverage skills, or showing off his dazzling moves with highlight reel punt returns, there wasn’t anything Sanders couldn’t do on a football field. And then he joined the Redskins.
In 2000, new owner Dan Snyder, lured Sanders (33 years old at the time) to Washington with an absurd eight-year, $56 million contract. Sanders had four interceptions in 2000, then abruptly decided to retire before the start of the 2001 season. According to reports, his relationship with head coach Marty Schottenheimer had soured to the point that Sanders decided to retire in protest of his coach. Sanders eventually returned to the NFL in 2004, as a member of the Baltimore Ravens.
Alvin Harper (Tampa Bay Buccaneers)
Alvin Harper made a name for himself in the NFL as a dangerous deep threat for the Dallas Cowboys, opposite Hall of Famer Michael Irvin. In 1994, Harper led the NFL with a ridiculous 24.9 yards per reception average. He parlayed that success into a lucrative free agent contract with the Buccaneers, to the tune of four years for $10.66 million.
But over the next two seasons, he was plagued with injuries, and never produced anything near the value that Tampa Bay paid for his services. By the time he left Tampa Bay, Harper had started in only 20 games and scored a grand total of three touchdowns. To put those dismal numbers into perspective, that’s $3.5 million per touchdown!
Sam Bradford (St. Louis Rams)
San Bradford might be the poster child for why the NFL adopted the the current rookie wage scale, as his 2010 first overall rookie contract was for a staggering 6 years, $78 million. Oh yeah, and $50 million in guarantees. What did the Rams receive for all that cash? 49 starts, an 18-30-1 record, and 31 missed games due to a sprained ankle and a torn (and then re-torn) ACL.
Bradford eventually emerged as a marginal starter in the NFL (though that might be putting it kindly), throwing for 103 touchdowns in nine NFL seasons. But he looked absolutely terrible in his final NFL season in 2018, and his career quickly and mercifully came to an end following that season.
Ryan Leaf (San Diego Chargers)
It’s funny to look back 20 years ago and wonder how there was ever a debate between Peyton Manning and Ryan Leaf for the top spot in the 1998 draft. Leaf was drafted second overall by the San Diego Chargers and received a five-year, $31.25 million contract with an $11.25 million signing bonus.
That might not seem like a lot of money in today’s NFL, but rest assured, that was a handsome figure in the late 1990’s. And as we all know, Leaf didn’t earn a penny of that money. In just two seasons with the Chargers, Leaf went 4-14 as the starter with 13 touchdowns and a whopping 36 interceptions. But hey, three of his four wins came on QB led game-winning drives.
Jamarcus Russell (Oakland Raiders)
Who can forget the fact that heralded NFL Draft analyst Mel Kiper raved about Jamarcus Russell’s private workout, comparing his passing ability to that of John Elway? Russell had one of the strongest arms we’ve ever seen from an NFL Draft prospect, but one of the worst work ethics we’ve seen from a quarterback prospect as well.
After the Oakland Raiders made him the #1 pick in the 2007 NFL Draft, they rewarded Russell with a 6-year, $61 million contract, including $32 million in guaranteed money. But Between his battles keeping his weight down, and his well-publicized issues with misusing codeine, Russell was out of the NFL just three seasons after being selected #1 overall.
Albert Haynesworth (Washington Redskins)
Albert Haynesworth’s infamous seven-year, $100 million contract is regarded as one of the very worst contract in the history of professional sports. Even after Haynesworth publicly declared that “You’re not going to remember Albert Haynesworth as a bust” in his introductory press conference, he was exactly that. From the very beginning of his time in D.C, Haynesworth presented problems for the coaching staff. The trouble began when he refused to participate in off-season workouts, and then arrived at training camp in poor physical condition, unable to pass a basic fitness test. The final straw came when Haynesworth publicly criticized the coaching staff, then decided to skip a series of practices.
Desperate to get Haynesworth off the team, the Redskins traded the disgruntled big man to the Patriots for a low round draft pick. As expected, Haynesworth got into a fight with an assistant coach in New England, and was waived from the team just three months after the trade.
There is no doubt that Albert Haynesworth and his mammoth contract is the worst deal in NFL history.