The 10 Worst Free Agent Contracts in NFL History

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Each and every year, NFL teams will spend feverishly in free agency in an attempt to find that extra piece that can help their team win a championship.

While there have been plenty of times in which these signings have worked out tremendously for an organization, there have been numerous occasions when these deals never quite worked out.

When trying to determine the worst free agent contracts in NFL history, many factors come into play: the overall dollar amount combined with the amount of production the player had during his tenure with the organization. 

Here are the 10 worst free agent contracts in NFL history. 

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Contract: 8 years, $66 million ($16 million guaranteed)

The 16th overall pick of the Tennessee Titans in 1999, Jevon Kearse broke onto the scene his rookie season, amassing 14.5 sacks on his way to his first Pro Bowl appearance and was named the AP NFL Defensive Rookie of the Year.

He put up double-digit sack totals in his next two seasons until getting derailed by a foot injury in 2002. He finished the 2003 season with a 9.5 sacks and was the most sought after defensive player in free agency.

He signed with the Philadelphia Eagles who made him the highest-paid defensive lineman in NFL history at that time, signing him to an eight-year contract worth $66 million.

His first two seasons were relatively productive, finishing both years with 7.5 sacks. But considering what he was being paid, his performance was disappointing. 

A terrible knee injury shortened his 2006 season and he was never quite able to return to being one of the league's most feared pass-rushers.

After a sub-par 2007 he was released by the Eagles, finishing his four-year tenure in Philadelphia with 22 sacks and he pocketed nearly $30 million. 

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Contract: 5 years, $12.5 million ($3.5 million guaranteed)

A former 12th round pick of the Dallas Cowboys in 1991, Larry Brown was an average at best cornerback during the first four seasons of his career.

He burst into the limelight in 1995, finishing the season with six interceptions and two touchdowns, and he picked off the Pittsburgh Steelers' Neil O'Donnell twice in Super Bowl XXX en route to winning the Super Bowl MVP award.

His five-year, $12.5 million deal was quite lucrative for the time at the position, but he struggled to adapt to the Raiders more aggressive man-coverage when he was more adept to playing zone-coverage in the Cowboys' scheme. 

In two seasons with the Raiders, Brown appeared in just 12 games, with only one start, before being released after the 1997 season.

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Contract: 6 years, $30 million ($10 million guaranteed)

A former second-round pick of the Oakland Raiders in 2000, Jerry Porter spent the early portion of his career playing behind Jerry Rice and Tim Brown.

His first breakout season came in 2002 when he hauled in 51 catches for 688 yards and nine touchdowns and helped lead the Raiders to Super Bowl XXXVII. The Raiders lost to the Tampa Bay Buccaneers by a score of 48-21, but he did haul in a 39-yard touchdown. 

After Rice was traded to the Seattle Seahawks after four games in 2004, Porter assumed the starting role and finished the season with 64 catches for 998 yards and nine touchdowns. He backed up his strong 2004 campaign with 76 catches for 942 yards and five touchdowns in 2005.

After a falling out with head coach Art Shell in 2006, he bounced back in 2007, catching 44 balls for 705 yards and six touchdowns. He parlayed his 2007 season into a six-year, $30 million deal from the Jacksonville Jaguars the following February.

That May he underwent surgery for his hamstring, missed all of training camp and the preseason and did not play until Week 4 against the Houston Texans. 

He appeared in 10 games for the Jaguars that season, finishing with just 11 catches for 181 yards and one touchdown.

In February of 2009, less than a year after signing his contract, the Jaguars released Porter. According to the USA Today, then general manager Gene Smith said of his release, "We just have to learn from our mistakes and move on."

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Contract: 6 years, $35 million ($12.5 million guaranteed)

While many names on this list are here because of what they did not do on the field, LeCharles Bentley is on this list for never being able to get on the field. 

After four productive seasons with the New Orleans Saints that saw him named to two Pro Bowls, Bentley, a Cleveland native, returned to his roots when he signed with the Cleveland Browns in 2006.

"I can die happy now," said Bentley during his first press conference with the team (via ESPN.com). "This has been my dream."

Bentley's dream quickly became a nightmare as he tore his patellar tendon in his first training camp and missed the entire 2006 season. His nightmare continued as he struggled in his rehab and eventually contracted a staph infection. 

He was cleared to return for the 2007 season, but he again suffered a setback and failed to make it on the field that season and never played a down for the Browns or any other NFL team.

According to NFL.com, Bentley filed a lawsuit in 2010 claiming the Browns had failed to warn him about previous players contracting staph in their facility and according to a Browns source, Bentley and Browns owner Randy Lerner settled out of court on "an agreement that was fair."

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Contract: 8 years, $62 million ($15 million guaranteed)

After an MVP season in 2005 in which Shaun Alexander rushed for 1,880 yards and scored 27 touchdowns, he signed an eight-year, $62 million deal with $15 million guaranteed with the Seattle Seahawks.

From 2001 to 2005, Alexander was one of the most productive running backs in the league. During that time he rushed for at least 1,100 yards a season and finished with 7,504 yards on 1,653 carries with 87 touchdowns. 

He missed six games in 2006 due to a foot injury and finished with 896 yards on 252 carries. Despite playing in 13 games in 2007, he finished with just 716 yards on 207 carries.

His injuries and lack of production led the Seahawks to release him in April of 2008. Then Seahawks' president Tim Ruskell said why Alexander received such a lucrative contract in the first place, saying (via ESPN.com), "I thought because Shaun had not been injured through his career, playing the odds I said ... 'If you are going to bet on a guy, bet on a guy who's not been hurt or had that propensity.' That was the case with Shaun."

It is no secret that NFL running backs have a short shelf life in the NFL. While Alexander was indeed coming off of his best year in the NFL, the Seahawks were relying on him to repeat that success and it never materialized. 

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Contract: 7 years, $47 million ($12 million guaranteed)

The eighth overall pick of the Arizona Cardinals in 1999, David Boston did not come into his own until the 2000 season. In 2000 and 2001, Boston had a combined 2,754 yards receiving on 169 catches with 15 touchdowns.

A knee and foot injury derailed his 2002 season as he was only able to participate in eight of the Cardinals' 16 games. He still finished the season with 32 catches for 512 yards and two touchdowns.

He hit the free agent market in 2003 and, despite being a two-time violator of the NFL's substance abuse policy, the San Diego Chargers signed him to a contract worth $47 million for seven years with $12 million guaranteed. 

Boston played relatively well in his one and only season in San Diego, catching 70 passes for 880 yards and seven touchdowns, but teammates criticized his work ethic, and he was suspended for one game following an argument with a coach (via ESPN.com). 

Because of his clashes with teammates and the coaching staff, the Chargers shipped him to Miami for a sixth-round pick and a player to be named later. 

Boston did not play a game for the Dolphins in 2004 after suffering a knee injury and getting suspended four games by the league for testing positive for steroids (via ESPN.com).

Boston played five games in 2005 for the Dolphins before being released. He briefly reemerged with the Tampa Bay Buccaneers in 2007, but never appeared in a game. 

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Contract: 7 years, $53 million ($8.5 million guaranteed)

Arguably one of the greatest cornerbacks to ever play the game, Deion Sanders had successful stints with the Atlanta Falcons, San Francisco 49ers and Dallas Cowboys before the Washington Redskins decided to give the then 34-year-old a seven-year, $53 million deal with $8.5 million guaranteed.

He did not have a bad season in 2000—he played all 16 games and had four interceptions, but he decided to retire at the end of the season.

Following his retirement, The Washington Post, citing anonymous sources, reported there was a settlement reached that had Sanders returning an amount less than $2.5 million of the $8 million he was given as guaranteed money (via CNNSI.com).

Regardless of how productive he was in 2000, Redskins owner Daniel Snyder proved that he had no problem throwing money at a 34-year-old who likely only had one or two seasons left in him. 

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Contract: 7 years, $30 million ($10 million guaranteed)

The 20th overall pick in the 2001 NFL draft by the St. Louis Rams, Adam Archuleta quickly excelled in the Rams' Cover 2 defense. 

In his five seasons in St. Louis, he was best known for his ability to get after the quarterback, notching 15 sacks during his tenure, including five in 2003. 

After signing with the Redskins and becoming the highest-paid safety in the game, Archuleta quickly fell out of favor with head coach Joe Gibbs as he struggled in the deep passing game—he was continually burnt deep. The team turned to veteran Troy Vincent to replace him at strong safety and he finished the season playing mostly special teams. 

His one season in Washington was enough for the Redskins as they traded him to the Chicago Bears in March of 2007 for a sixth-round pick. The Bears agreed to pay him $8.1 million over the next three years (via ESPN.com).

On his way out of Washington, Archuleta told The Washington Times:

I didn’t see it coming. It kind of snowballed into kind of a mess. I won’t pretend I went there and lit it up. When you look at the performance of the team and the defense and you look at individual performances, I don’t think mine was really out of line. In a certain sense, I hit rock-bottom, so I learned a lot about myself. I think I’m better as a person and better as a football player because of it. This move is best for the Bears, best for the Redskins and best for me.

Archuleta did not perform much better in Chicago and was subsequently released in May of 2008. He never played another down in the NFL. 

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Contract: 6 years, $55 million ($16 million guaranteed) 

A star at Florida State and the 20th overall pick in the 2002 draft for the Green Bay Packers, Javon Walker had four solid, albeit average, seasons with the Packers before being traded to the Denver Broncos for a second-round pick in 2006.

Walker topped the 1,000-yard mark in 2006 for the Broncos, but was subsequently released after the 2007 season after he only played in eight of the team's 16 games.

After his release, the Oakland Raiders stepped in and signed Walker to a six-year, $55 million contract that included $27 million in the first three years and $16 million guaranteed. The contract was staggering for a player who struggled a year prior compared to the fact that Randy Moss had just received a $27 million contract over three years with the New England Patriots (via NFL.com).

He started seven games in 2008 before an injury ended his season. He finished with just 15 catches for 196 yards and one touchdown. He followed up his poor 2008 season by playing in just three games for the Raiders in 2009 and was released.

Walker pocketed $21 million during his two unproductive years in Oakland and while he spent some time with the Minnesota Vikings during the 2010 offseason, he was cut before the start of the regular season. 

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Contract: 7 years, $100 million ($41 million guaranteed)

During his tenure with the Tennessee Titans, Albert Haynesworth was one of the most feared defensive players in the league. While he was mostly feared for his ability to get after the quarterback, he was known for his temper and on the field incidents.

In a game against the Dallas Cowboys in October of 2006, Haynesworth stomped on Cowboys' center Andre Gurode and he was eventually suspended five games for his actions. 

Despite his actions, he continued to be a force on the field and he amassed 14.5 sacks combined in 2007 and 2008 and was named to the Pro Bowl and All-Pro teams both seasons.

Haynesworth hit the free agent market following the 2008 season and was widely regarded as the best free agent available. 

In late February of 2008, Haynesworth signed a seven-year, $100 million deal with the Washington Redskins that included a then NFL-record $41 million in guaranteed money. During the first 13 months of the contract, Haynesworth would earn approximately $32 million (via ESPN.com).

His tenure in Washington started off rocky when he declined to participate in the team's offseason workouts and was unable to pass the Redskins' basic fitness test (via The Washington Post).

He clashed with defensive coordinator Greg Blache and his 3-4 scheme, telling Jason Reid and Dan Steinberg of The Washington Post at the time that he couldn't "survive another season in this system if it stays the way it is."

The final straw came in 2010 when the team suspended him for the final four games of the season for conduct detrimental to the team (via CBSNews.com).  

The team traded him to the New England Patriots in the summer of 2011 for a fifth-round pick. He lasted six games in New England before being released. He was signed by the Tampa Bay Buccaneers for the remainder of the season before the team released him in February of 2012. 

Former teammate Chris Cooley shed light on the situation, telling ESPN 980 (via The Washington Post) in 2013 that:

(Haynesworth) was TRYING to get released by the team. His goal was to come here, make a large signing bonus, and then get released and not have to do any of the work. He didn't care about the back end of that contract, he didn't care about making all of that money. His idea was, you paid me for what I did in the past, and my goal is to be released as soon as possible and basically take $33 million from you for absolutely nothing.

Given the amount of money he was paid, combined with his lack of production, Albert Haynesworth goes down as the worst free agent signing in NFL history.