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Every NFL Team's Most Regretful Contract In Franchise History

In North America, we have access to virtually every sport known to man, but even with all of the available options, there are really only four sports that really matter, and they would be football, hockey, baseball, and basketball. Each of these sports have their own professional leagues, and they all produce billions of dollars in revenue every single year, but none of them are as financially successful as the National Football League. Last year alone, the NFL made $14 billion in revenue, and it did so by providing audiences with relatively high-scoring games that showcased the very best players that the sport has to offer.

If a person is lucky enough to make it to the NFL, then they are probably living a very comfortable lifestyle, as many of the players in the league are signed to contracts worth millions of dollars. It goes without saying that the better players get bigger contracts, but there are also cases in which players are given expensive contracts based on their past performances, or their future potential. In every professional sport, there are good contracts, and bad contracts, but the bad ones really stick out as they can negatively effect a team's performance for one or more seasons, and in football, those types of contracts are very problematic because of the guaranteed money involved. Contracts usually turn out bad as a result of poor performance or injuries, and the NFL has been filled with bad contracts for a long time, and this list will try to identify the worst contract that every franchise has handed out.

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32 Arizona Cardinals: Jermaine Gresham

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As a franchise, the Arizona Cardinals have been around for 120 years, which means that the team has had plenty of time to make some big mistakes, but their most recent mistake may really haunt them. The team signed tight end Jermaine Gresham in 2015, and in 2 years with the Cardinals, he managed to record a catch rate of roughly 60%, while scoring a combined 3 touchdowns. Such numbers would normally not amount to a payday, but in this case, Arizona decided to do the opposite, and signed Gresham to a 4-year contract, a contract he will doubtfully be able to live up to seeing as it is worth $28 million, with $16.5 million guaranteed.

31 Atlanta Falcons: Michael Vick

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The Atlanta Falcons are pretty happy with Matt Ryan as their starting quarterback, seeing as he got them to the Super Bowl in 2016, and although he failed to win the championship that year, the team still gave him a 5-year, $150 million contract this offseason, with $100 million guaranteed. Before Ryan came along though, the Falcons thought that Michael Vick would be the guy to bring them a championship, which is why they signed him to a 10-year, $130 million contract, but as we all know, 3 years into it, off the field antics put a hold on his career. The team may have gotten rid of him shortly after the story broke, but they still had to pay him $35 million.

30 Baltimore Ravens: Elvis Grbac

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The year 2000 saw the start of a new millennium, but it also saw the Baltimore Ravens win their first Super Bowl title, a championship that they won without having a legitimate starting quarterback.

The Ravens thought they could become a dynasty with the right guy, which is why they went out and signed Elvis Grbac to a 5-year contract worth $30 million.

It was a move they made because Grbac won a Super Bowl in San Francisco as a backup. In his first and only season with Baltimore, Grbac threw for 3,033 yards with 15 touchdowns and 18 interceptions, numbers that the team did not like, which is why they cut him during the offseason.

29 Buffalo Bills: Derrick Dockery

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The Buffalo Bills have seemingly been in disarray for a number of years, as they have messed up draft picks and free agent signings, which is why Derrick Dockery finds himself on this list. The former offensive lineman went to Buffalo after they gave him a 7-year contract worth $49 million, a move that made him the 3rd highest paid player ever at his position. Dockery spent just 2 seasons with the Bills before they traded him to Washington to free up cap space, which means that they knew he could never live up to his contract, too bad they did not realize this before they gave him a guaranteed $18 million.

28 Carolina Panthers: Sean Gilbert

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Franchise tags can be a problem, because if you sign a player who has one on them, your team will have to give something up, and that is exactly what happened with Sean Gilbert and the Carolina Panthers in 1998. The Redskins placed a franchise tag on the defensive tackle, so the Panthers had to give Washington 2 1st round picks as compensation for signing Gilbert to a 7-year, $46.5 million contract. After a good first season, Gilbert had a combined 9.5 sacks over the next 4 seasons, and when you consider the fact that he developed hip problems, it makes sense that he was released in 2003.

27 Chicago Bears: Jay Cutler

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While playing for Denver in 2008, Jay Cutler had a Pro-Bowl season, which is why the Chicago Bears traded for him, with the hopes that he would become their franchise quarterback. In his first 4 seasons with the team, Cutler dealt with multiple injuries, and mediocre performances, but that did not stop the Bears from re-signing him in 2013 to one of the biggest contracts ever. Cutler was signed to a 7-year contract worth $126.7 million, with $54 million guaranteed, but the poor play and injuries continued to mount, to the point that he was bought out and released in 2017.

26 Cincinnati Bengals: Antonio Bryant

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Over the past 15 years or so, the Cincinnati Bengals have had bad luck when it comes to certain players, mainly because they found themselves in legal trouble, but Antonio Bryant dealt with even more issues. When he came into the league, the wide receiver's future looked promising, but numerous injuries squashed those dreams, but his medical history did not stop the Bengals from taking a shot with him. That shot turned out to be a 4-year, $28 million contract, but thanks to a knee injury, and poor showings in practice, he never played a single game for Cincinnati, and was subsequently cut before the 2010 season even started.

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25 Cleveland Browns: LeCharles Bentley

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When you get the chance to play for your hometown team, it truly feels like a dream come true, and that is exactly how LeCharles Bentley felt when the Cleveland Browns signed him in 2006.

The former guard was signed to a 6-year, $35 million contract, which came with a guaranteed $12.5 million, and although he was considered to be a top-rated talent, he ended up never playing in a single game for the Browns.

During his first day of training camp, he ruptured a patellar tendon, which caused several staff infections that almost cost him his leg, and after missing from the field for 682 days, he was released by the team in 2008.

24 Dallas Cowboys: Mike Vanderjagt

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After a rather lengthy stint in the Canadian Football League, placekicker Mike Vanderjagt finally got his dream job in the NFL, after being signed by the Indianapolis Colts, but his numbers were never as impressive as they should have been with a Peyton Manning led offense. When Adam Vinatieri became available in 2005, the Colts decided to part ways with Vanderjagt, which opened the door for the Dallas Cowboys to sign him to a 3-year, $4.5 million contract, with $2.5 million guaranteed. Vanderjagt played just 1 season, and in those 10 games, he posted a 72.2% kick completion on just 18 attempts, which were both career lows.

23 Denver Broncos: Dale Carter

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Dale Carter started his career with the Kansas City Chiefs in 1992, and during his 7-year tenure with the team, he became a 4-time Pro Bowler who missed just 8 games, which made the cornerback a sought after piece during the 98 offseason. The Denver Broncos nabbed him in hopes of weakening the defense of one of their division rivals, and signed him to a 6-year, $34.8 million contract. His numbers in Denver were never what they were in Kansas City, and he ended up missing the entire 2000 season after being suspended for violating the league's substance abuse policy. The Broncos then decided to release him the following year.

22 Detroit Lions: Scott Mitchell

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In the early 90s, the Detroit Lions were looking for a quarterback, which is why they went out and signed Scott Mitchell in 1994 to a 3-year deal worth $11 million, and in the final year of that deal, he put up very mediocre numbers, which included 17 interceptions. Normally, mediocrity is not rewarded with a pay increase, but the Lions decided to re-sign Mitchell to a 4-year, $21 million contract, with a guaranteed $8 million. After signing the contract, Mitchell went on to play in just 2 games before being replaced by his backup, which is why he found himself in Baltimore the following season.

21 Green Bay Packers: Martellus Bennett

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The Green Bay Packers have managed to steer relatively clear of bad contracts, but that did not stop them from making a pretty bad signing last year, a signing that saw tight end Martellus Bennett join the team. Bennett was signed to a 3-year, $21 million contract, but when all was said and done, he only played in 7 games before being placed on waivers by the team. The reason why this move occurred, was because Bennett failed to disclose a medical condition with the team, and after he was picked up by New England, the Packers had to take him to court to try and recoup his signing bonus.

20 Houston Texans: Brian Cushing

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When the Houston Texans drafted Brian Cushing in 2009, it looked as though they might have gotten the steal of the draft, especially when you consider how well he ended up playing on the field. When healthy, there was no doubt that Cushing was one of the best linebackers in the league, and it is because the team expected him to stay relatively healthy, that they signed him to a 6-year contract in 2013, worth $56 million with a $9 million signing bonus, and a guaranteed $28 million. Unfortunately, Cushing has since dealt with knee issues, and after being suspended for 10 games last season, the Texans finally decided to release him this past February.

19 Indianapolis Colts: Andre Johnson

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Andre Johnson spent the first 12 seasons of his career with Houston, but when he finally became a free agent in 2015, the Colts decided to snatch him from their division rival, and signed him to a 3-year, $21 million contract. When the 2015 season started, Johnson was the NFL's active leader in receiving yards, but he was unable to provide the Colts with the offense they were expecting. Johnson was released in 2016 after recording 4 touchdowns with just 41 receptions and 503 yards.

18 Jacksonville Jaguars: Jerry Porter

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Usually, when a team decides not to re-sign a player, it is because they do not believe that he is worth keeping around, which is exactly the reason why Oakland allowed someone else to sign Jerry Porter in 2008. The former wide receiver signed a 6-year contract with the Jacksonville Jaguars worth $30 million, with $10 million guaranteed. Porter played in just 10 games during his first and only season with the Jags, where he had just 11 receptions and 181 yards. Apparently the Jags did not mind throwing away $10 million, seeing as they cut him in 2009, which was a wise decision seeing as he went on to never play in another NFL game.

17 Kansas City Chiefs: Justin Houston

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The Kansas City Chiefs have managed to put together some good regular season records as of late, but it is a real shame that those records have not really amounted to anything during the playoffs. One of the reasons why the Chiefs have performed so well is because they have Justin Houston on their roster, who was believed to be the best linebacker in the league, which is why they signed him to a 6-year extension in 2015 worth $101 million, of which $52.5 million was guaranteed. Since signing that deal though, Houston has dealt with several injuries, and has amassed just 11.5 sacks, making him not worth the $22 million cap hit.

16 Los Angeles Chargers: David Boston

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In 2001, wide receiver David Boston caught 98 passes for 1,598 yards and 8 touchdowns while with Arizona, and it was because of that offensive potential that the then San Diego Chargers signed him to a 7-year, $47 million contract in 2003. As it turned out though, Boston was unable to leave his attitude in Arizona, as he clashed with teammates and members of the coaching staff, and when you combine that with his sluggish habits during practice, it is no wonder that they traded him after 1 season. That proved to be a smart move, as Boston went on to have injury and legal problems following the 2003 season.

15 Los Angeles Rams: Sam Bradford

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Like every other team, the Rams need a quality starting quarterback, and they thought they had one with Sam Bradford, which is why they drafted him 1st overall in 2010, when the team was still in St. Louis. That same year, the team signed the young QB to a 6-year, $78 million contract, of which $50 million was guaranteed, but as the team quickly found out, he was at best an average player not worthy of such a contract. In 3 seasons with the Rams, Bradford went 15-26-1, and then missed the 2014 season due to an ACL injury, and those were the primary reasons why the Rams traded him away in 2015.

14 Miami Dolphins: Mike Wallace

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While playing in Pittsburgh (2009-12), Mike Wallace became a Pro Bowl wide receiver; in fact, he performed so well during that time that the Miami Dolphins believed that he would be a perfect fit for their offense.

Miami signed him to a 5-year, $60 million contract in 2013, but it became apparent very early on that he did not mesh with the Dolphins' style of play, which resulted in mediocre offensive numbers.

After just 2 seasons, the Dolphins had enough of Wallace, and traded him to Baltimore, where he started putting up good numbers again.

13 Minnesota Vikings: Daunte Culpepper

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While with the Minnesota Vikings in 2004, Daunte Culpepper threw for 4,717 yards, which resulted in 39 touchdowns and only 11 interceptions; that performance led to a pretty big payday.

Following that impressive season, the team rewarded him with a 10-year, $102 million contract, but when the 2005 season came around, he threw 8 interceptions and 0 touchdowns in the first 2 games.

A few weeks later, he suffered a torn ACL, PCL, and MCL. The Vikings' backup then went on to perform well, which is why the team did not mind trading Culpepper after just 1 season.

12 New England Patriots: Adalius Thomas

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A lot of people may hate the New England Patriots, but all of that hate cannot diminish the fact that they are the most successful team since the year 2000, mainly because of Tom Brady and Bill Belichick. In 2007, the Pats believed that they needed help on defense, which is why they went out and signed linebacker, Adalius Thomas to a 5-year, $35 million contract, of which $25 million was guaranteed. Unfortunately, Thomas did not like New England's play style, and not only did that cause a rift between himself and his teammates, it also caused his numbers to drop, which explains why they released him after the 2009 season.

11 New Orleans Saints: Jairus Byrd

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While playing for the Bills, safety Jairus Byrd became a 3-time Pro Bowler, and thanks to his defensive abilities, he was able to land a pretty sweet contract with the New Orleans Saints in 2014. That contract saw the team give him $56 million over 6 years, with $28 million guaranteed, which would have been fine if he was able to perform the way that he did while in Buffalo. During the 2014 season, Byrd tore his meniscus, and he has never been the same player since, as he went on to have 3 straight disappointing seasons, which resulted in the Saints releasing him in 2017.

10 New York Giants: Lavar Arrington

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Lavar Arrington spent the first 6 years of his career with the Redskins, and half of those seasons ended with him making an appearance in the Pro Bowl, and because he was considered to be a great linebacker, he became a coveted free agent. It was the New York Giants who landed him, and they did so by giving him a 7-year contract worth $49 million in 2006. In his first and only season with the Giants, Arrington suffered a ruptured Achilles tendon, which effectively ended his career, and which forced the team to release him in 2007.

9 New York Jets: Muhammad Wilkerson

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Over the past decade, the New York Jets have not been that successful, as they have made some poor contract and draft decisions, and one of those poor contracts belonged to defensive end, Muhammad Wilkerson. After 3 good years, the Jets re-signed Wilkerson in 2016 to a 5-year, $86 million contract, which came with a $15 million signing bonus, and a guaranteed $53.5 million. After signing the deal though, his defensive numbers fell way off, including last season where he had just 3.5 sacks, 4 defended passes, and 1 interception, and those numbers are why he was released this offseason.

8 Oakland Raiders: JaMarcus Russell

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When you get picked 1st overall in the draft, you are expected to help turn a franchise around, but that is not what happened when the Oakland Raiders drafted quarterback JaMarcus Russell in 2007. After drafting him, the Raiders were quick to sign him to a 6-year, $68 million contract, with $31.5 million guaranteed.

As luck would have it, Russell turned out to be one of the biggest draft busts in NFL history.

Russell was incredibly inconsistent, and started in just 25 games where he posted a 7-18 record with 23 interceptions, results that ultimately led to his 2010 release.

7 Philadelphia Eagles: Jevon Kearse

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The Philadelphia Eagles are the defending Super Bowl champions, but they came close to winning the title in 2005 when they lost to the Patriots in the championship game, which turned out to be Jevon kearse's only chance to get a ring. Kearse was a defensive end who the Eagles signed in 2004 to an 8-year, $66 million contract, and he started his new contract off with decent numbers, including 7.5 sacks in 2 straight seasons. After the 2005 season however, he suffered a lateral meniscus tear and a fractured fibia, which should have been career-ending, and although it was not, he was never the same player again, which is why the Eagles released him in 2008, but only after paying him over $29 million.

6 Pittsburgh Steelers: Maurkice Pouncey

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The Steelers are one of the NFL's most historic and successful franchises, and although they have not made many high profile mistakes, they currently have quite a few bad contracts. One of those bad contracts belongs to Maurkice Pouncey, a center who has been with the team since 2010, and he is currently in the middle of a 5-year, $44.13 million contract, which came with a $13 million signing bonus and another guaranteed $13 million. Considering he has been to the Pro Bowl 6 times while with Pittsburgh, the contract seems fine, but Pouncey has been dealing with serious knee problems the past couple of years, which will make the final 2 years of his deal a real issue.

5 Seattle Seahawks: Shaun Alexander

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In 2005, running back Shaun Alexander had an amazing season, with 1,880 yards and 27 touchdowns, a performance that got him named that year's MVP, so it only made sense that he would get rewarded come contract time. That reward came with the Seattle Seahawks re-signing him to an 8-year contract worth $62 million, but like many other athletes who get paid, his production saw a significant decline. Alexander was never able to break the 1,000 yard mark again, and he became ravaged by leg injuries, factors that forced the team to cut him in 2008.

4 San Francisco 49ers: Colin Kaepernick

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Just because he decided to protest by not standing during the National Anthem, Colin Kaepernick is currently blacklisted from the NFL, which is really unfair seeing as he has the skills to work in the league. Like many people, the San Francisco 49ers believed that Colin had a lot of upside, which is why they decided to re-sign him in 2014 to a 5-year, $125 million contract, which came with a potential $54 million guaranteed. After re-signing, Colin's performance took a downwards turn, which made the team suffer, and it became clear that the 49ers were not happy with him, because when he asked to restructure his deal, they turned him down, allowing him to become a free agent in 2017.

3 Tampa Bay Buccaneers: Alvin Harper

The Tampa Bay Buccaneers were looking to make a splash during the 1995 offseason, which is why they went out and signed wide receiver, Alvin Harper to a 4-year contract worth $10.66 million. By today's standards, such a contract is not that big, but in 1995, players were getting less than they are now, so it essentially evens out, which is why Harper's tenure with the team was such a disappointment. Harper may have played well for the Cowboys, and helped them to win 2 Super Bowls, but his production fell off a cliff once joining Tampa Bay, as evidenced by the fact that he was released after 2 seasons, after starting in just 20 games where he had just 3 touchdowns.

2 Tennessee Titans: David Givens

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There are players who do not put up big numbers during the regular season, and those players usually do not get rewarded with big contracts, but if those players are able to perform in the playoffs, that all changes. Thanks to a couple of good playoff performances, David Givens helped the Patriots win 2 Super Bowls, and all those touchdowns amounted to the Tennessee Titans signing the wide receiver to a 5-year, $24 million contract in 2006. His first season with the team also turned out to be his last, as he dealt with several injuries, including an ACL tear in week 10, an injury which resulted in his 2008 release, and which ultimately ended his career.

1 Washington Redskins: Albert Haynesworth

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The Tennessee Titans may have had their ups and downs in the past, but they did have one bright spot: Albert Haynesworth, who at the time was considered one of the best defensive tackles in the league. When he became a free agent in 2009, the Washington Redskins signed him to a 7-year, $100 million contract, with $41 million guaranteed, a contract that is considered to be one of the worst in NFL history. In 2 years with Washington, he had just 6.5 sacks, refused to take part in offseason workouts, failed a fitness test, and got into arguments with the coaching staff, which is why he was shipped off to New England in 2011.

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