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- Contract value: $85 million (5 years)
- Average salary: $17 million

The New York Jets had tons of to spend entering the 2019 offseason. Needing a defensive general, the Jets paid big money to nab C.J. Mosley of the Baltimore Ravens. Since his 2014 rookie year, Mosley made four Pro Bowls in Baltimore but was largely during his first year in New York.

- Contract value: $85 million (5 years)
- Average salary: $17 million

Seeking to upgrade their defensive line in 2016, the New York Giants paid out in guarantees to free agent Olivier Vernon. Injuries derailed Vernon’s time in New York, and he was before the 2019 season, as the Giants sought to save salary.

- Contract value: $85.5 million (5 years)
- Average salary: $17.1 million

Dee Ford collected 13 sacks in 2018 and wanted to get paid. The Kansas City Chiefs were unable to reach a contract extension with Ford and , where he signed his current five-year deal. Ford tallied this season and became the again.

- Contract value: $85.5 million (9 years)
- Average salary: $9.5 million

In 1999, Troy Aikman signed what was then one of the biggest contracts in NFL history, with an extension that would run until 2007. However, as the Dallas Cowboys’ dynasty came to an end, by 2001, Aikman’s contract became an albatross, and he was cut before a bonus kicked in. Aikman retired rather than play for another team.

- Contract value: $90 million (6 years)
- Average salary: $15 million

Before the 2019 season, Dallas Cowboys running back Ezekiel Elliott held out for a new contract. Elliott's game of chicken worked, as he received an extension that included in guaranteed money, making him the richest running back in NFL history. Elliott in rushing in two of his first three years as a pro.

- Contract value: $90 million (5 years)
- Average salary: $18 million

In 2018, the Detroit Lions signed Matt Patricia as head coach, and the former New England Patriots assistant was expected to build a team based on the “.” Patricia began poaching former Patriots and in March 2019 snagged , who spent his first four seasons in New England. Flowers was the Patriots’ and was coached by Patricia when he was New England’s defensive coordinator.

- Contract value: $90 million (5 years)
- Average salary: $18 million

Odell Beckham Jr. wowed fans with his acrobatic catches during his time with the New York Giants, and Big Blue rewarded the former LSU star with a contract in 2018 that included guaranteed. However, Beckham was less than a year later to the Cleveland Browns, ending a dazzling yet in New York.

- Contract value: $90 million (9 years)
- Average salary: $10 million

The contract of former NFL running back Stephen Davis serves as Example A of how weird football contracts can be. The 2000 Davis deal with the Washington Redskins was worth over $90 million, with incentives that could make it worth almost $140 million. However, only a was guaranteed, and Davis was after the 2002 season.

- Contract value: $94 million (4 years)
- Average salary: $23.5 million

With Patrick Mahomes ready to take over as quarterback of the Kansas City Chiefs, former starter Alex Smith went to Washington and signed a massive new contract. Smith ended up suffering a that threatened his life, yet the signal-caller still hopes to play football again one day.

- Contract value: $96 million (7 years)
- Average salary: $13.7 million

Toward the end of Adrian Peterson's monster seven-year deal, the Minnesota Vikings' star running back worried the final years Peterson voiced his displeasure without the guarantees and eventually earned his full salaries over the next two seasons, but 2016 would be the end of Peterson's tenure in Minnesota. In 10 years with the Vikings, Peterson ran for .

- Contract value: $96.3 million (5 years)
- Average salary: $19.3 million

Last summer, Michael Thomas held out and was rewarded with a contract that paid him , the most of any non-quarterback in NFL history. Thomas went on to catch , both NFL highs in 2019.

- Contract value: $97.6 million (8 years)
- Average salary: $12.2 million

Offensive lineman Tyron Smith’s with the Dallas Cowboys gave him the highest total-value contract of any player in his position. However, Smith, a seven-time Pro Bowler, is not the highest-paid lineman per year, as that title goes to , who just signed a three-year, $66 million deal in April.

- Contract value: $98 million (7 years)
- Average salary: $14 million

In 2004, the Indianapolis Colts gave franchise quarterback Peyton Manning a $98 million deal that was . Manning won one Super Bowl in 13 years in Indianapolis, then signed an almost equally monstrous contract .

- Contract value: $100 million (5 years)
- Average salary: $20 million

After signing quarterback Dak Prescott to a long-term deal, the Dallas Cowboys tied up his favorite target. , who was traded to Dallas in 2018, signed a five-year pact in March. Not everyone was enamored with the signing, though, as former NFL coach Rex Ryan described Cooper as, well...let’s just say it’s .

- Contract value: $100 million (10 years)
- Average salary: $10 million

When Brett Favre signed a $100 million extension in 2001, he said he'd be a "" Favre lasted in Green Bay through 2007 before he played with the New York Jets and Minnesota Vikings. Favre retired with , fourth-most all time.

- Contract value: $100 million (7 years)
- Average salary: $14.3 million

Albert Haynesworth’s 2009 contract extension , the most of any NFL deal ever at that point. Haynesworth only played as injuries slowed the career of one of the league’s more dominant defensive lineman. Recently, Haynesworth .

- Contract value: $100 million (6 years)
- Average salary: $16.7 million

J.J. Watt’s 2014 contract extension guaranteed him , the most for any defensive player at the time. Watt has only played since signing the deal but remains one of the league’s top pass-rushers. He will be highly sought-after if he hits free agency when his contract runs out after the 2021 season.

- Contract value: $101 million (6 years)
- Average salary: $16.8 million

Justin Houston became the NFL’s with his massive nine-figure deal. Houston never matched his production pre-2015 and , where he played .

- Contract value: $102 million (8 years)
- Average salary: $12.8 million

In 2008, the Pittsburgh Steelers made Ben Roethlisberger the . Roethlisberger still suits up for the Steelers and has earned over over 16 seasons. Big Ben has earned six Pro Bowl nods and won two Super Bowl rings in Pittsburgh.

- Contract value: $102 million (10 years)
- Average salary: $10.2 million

Daunte Culpepper's 2003 contract made him in NFL history at the time (behind Donovan McNabb and Drew Bledsoe). Culpepper made the Pro Bowl each of the two following seasons, but his career became , and he exited the NFL after the 2009 campaign. Before playing pro football, Culpepper was drafted .

- Contract value: $102.6 million (6 years)
- Average salary: $17.1 million

Before the 2016 season, the Philadelphia Eagles inked Fletcher Cox to a new megadeal, expecting him to be an anchor of their defense for years to come. Cox has since made and helped the Eagles win a Super Bowl. Recently, Cox was named to the 2010s .

- Contract value: $103 million (10 years)
- Average salary: $10.3 million

Drew Bledsoe was Bill Russell, Ted Williams, and other Boston sports legends when he signed a 10-year deal with the New England Patriots in 2001. Months later, Bledsoe was , and a young upstart named Tom Brady took over as quarterback of the Patriots. Bledsoe left the Patriots in 2002.

- Contract value: $104 million (5 years)
- Average salary: $20.8 million

The Kansas City Chiefs, on the cusp of ascending to the top of the AFC, locked up Frank Clark before the 2019 season. Clark came from Seattle, where he had two seasons In the 2019 playoffs, Clark registered five sacks, and the Chiefs went on to win the Super Bowl.

- Contract value: $105 million (5 years)
- Average salary: $21 million

DeMarcus Lawrence blossomed from a second-round pick to one of the stalwarts of the Dallas Cowboys defense. Lawrence was rewarded with after two consecutive Pro Bowl nods. Last season, Lawrence recorded his lowest total of sacks when playing more than half a season.

- Contract value: $106.9 million (7 years)
- Average salary: $15.3 million

After helping the New York Giants upset the New England Patriots in Super Bowl XLII, Eli Manning was rewarded with a deal that made him Manning would win another Super Bowl MVP but was , as the Giants turned to rookie Daniel Jones. After the season, Manning retired.

- Contract value: $108 million (6 years)
- Average salary: $18 million

Despite Tony Romo’s for not coming up big in the playoffs, the Dallas Cowboys . Romo only played until 2016 but found success in the booth, where he is now the .

- Contract value: $110 million (5 years)
- Average salary: $22 million

, the Green Bay Packers made Aaron Rodgers the highest-paid player in the NFL by salary per season. Rodgers only played nine games in his first season under his new deal but remains firmly entrenched as the Packers’ starter. Or so it seemed until April...

- Contract value: $114 million (6 years)
- Average salary: $19 million

Despite a as a volatile player, Ndamukong Suh during the 2015 season. Suh only played three seasons in Miami but was recognized on the 2010s .

- Contract value: $114.1 million (6 years)
- Average salary: $19 million

After winning a Super Bowl MVP and cementing himself as one of the Denver Broncos’ best defensive players ever, Von Miller received . Miller also became one of the NFL’s most recognizable faces in a variety of . Recently, Miller spread awareness of COVID-19 after he .

- Contract value: $115 million (12 years)
- Average salary: $9.6 million

In 2002, Donovan McNabb became one of pro sports' richest men when the Philadelphia Eagles signed him . By 2009, the Eagles needed to McNabb's deal, and he was playing in Washington by the next season.

- Contract value: $115 million (6 years)
- Average salary: $19.2 million

Despite the Cincinnati Bengals’ lack of playoff success, they unofficially anointed Andy Dalton as their franchise quarterback for the foreseeable future . A megadeal made Dalton one of the richest players in the NFL, even with an 0-3 playoff record. In April, Dalton was released and .

- Contract value: $118 million (4 years)
- Average salary: $29.5 million

The Tennessee Titans made in Ryan Tannehill this offseason, believing that the former blue-chip prospect can finally fulfill his potential in Nashville. In 2012, Tannehill was the eighth overall pick, selected by the Miami Dolphins, but never made a Pro Bowl until he left Florida. Tannehill as Titans starter last season and led Tennessee to a surprise win over the New England Patriots in the playoffs.

- Contract value: $119.8 million (9 years)
- Average salary: $13.3 million

In 2003, the Cincinnati Bengals took Carson Palmer with the top pick in the draft. Two years later, the Bengals offered Palmer , believing he’d retire with the team. Palmer lasted in Cincinnati until 2010 before spending the second half of his career with the Oakland Raiders and Arizona Cardinals.

- Contract value: $120 million (8 years)
- Average salary: $15 million

The Arizona Cardinals made Larry Fitzgerald the richest player with this whopping 2011 deal. Two years earlier, Fitzgerald had the Cardinals on the cusp of a Super Bowl title, and despite not reaching the big game since, he remains one of the league’s most sure-handed receivers with . Next season, Fitzgerald will team with to form one of the NFL’s most lethal pass-catching duos.

- Contract value: $120.6 million (6 years)
- Average salary: $20.1 million

Is ? That remains one of football's most heated debates, but one thing is for sure: Flacco was paid like an elite quarterback. In 2013, the Baltimore Ravens signed Flacco to a deal that paid him per year on average, but last season, Flacco moved on to Denver, with Lamar Jackson the new starter in Baltimore.

- Contract value: $125 million (5 years)
- Average salary: $25 million

In the summer of 2017, the then-Oakland Raiders made the league’s highest-paid player. Carr was coming off two straight Pro Bowl seasons, and the Raiders appeared to be on the upswing with Amari Cooper, but the team has played sub-.500 ball under new coach Jon Gruden. Now Carr’s starting position may be in jeopardy due to Oakland’s signing of .

- Contract value: $126 million (6 years)
- Average salary: $21 million

The San Francisco 49ers signed to a huge contract in 2014, expecting him to be their quarterback of the future. However, Kaepernick of his deal after the 2016 season after losing the starting quarterback job amid his protests against racial inequality. Kaepernick has not played in the NFL since.

- Contract value: $126.7 million (7 years)
- Average salary: $18.1 million

The committed to Jay Cutler long-term in 2014 but only kept the quarterback in the Windy City through 2016. Cutler played one season with the Miami Dolphins before retiring. Cutler then became a star.

- Contract value: $128 million (4 years)
- Average salary: $32 million

One year after leading the Philadelphia Eagles to their first Super Bowl title, Carson Wentz was rewarded with a that was the largest in NFL history. Wentz made the Pro Bowl in 2017, but his status as the Eagles’ future quarterback is a bit muddled, with Philadelphia drafting in April.

- Contract value: $130 million (10 years)
- Average salary: $13 million

Michael Vick also held the title of when he signed a nine-figure deal with the Atlanta Falcons in 2004. Vick's fall from grace is well documented due to his involvement in . Vick played seven more years after serving a two-year suspension but never recaptured the glory that made him seem like on the field.

- Contract value: $132 million (8 years)
- Average salary: $16.5 million

After leading the NFL with in 2012, Calvin Johnson, also known as Megatron, was rewarded with a . Three years later, Johnson surprisingly while still in the prime of his career.

- Contract value: $134 million (4 years)
- Average salary: $33.5 million

Jared Goff helped the Los Angeles Rams reach the Super Bowl in February 2019 and was richly rewarded with a new contract . Goff threw for over 4,600 yards last season, but the former first-overall pick could not lead the 2018–19 NFC champions back to the playoffs.

- Contract value: $134 million (4 years)
- Average salary: $33.5 million

After signing a $110 million deal earlier in his career, Aaron Rodgers in 2018. However, the Green Bay Packers shocked many when they selected quarterback in the first round of the 2020 NFL Draft. Rodgers is 36 but still threw for and made the Pro Bowl last season.

- Contract value: $135 million (6 years)
- Average salary: $22.5 million

Aaron Donald posted a stunning 20.5 sacks in 2018. As a result, the Los Angeles Rams paid Donald handsomely, offering the .

- Contract value: $135 million (5 years)
- Average salary: $27 million

The Detroit Lions' decision to make the highest-paid player in the league in 2017 was met with some skepticism. Stafford had just completed a run of seven consecutive seasons with 4,000 or more yards but has only played in three playoff games. Stafford has been durable through much of his career, but his 2019 campaign ended prematurely due to a .

- Contract value: $137.5 million (5 years)
- Average salary: $27.5 million

One year after Matthew Stafford got paid like no other player before him, claimed the top spot with his $27.5 million average salary. Garoppolo was drafted in the second round in 2014 by the New England Patriots, but instead of becoming Tom Brady’s heir, he was shipped to San Francisco before the 2017 season. Garoppolo helped the 49ers reach the Super Bowl last season but struggled in the big game, .

- Contract value: $140 million (4 years)
- Average salary: $35 million

Garoppolo’s reign as the highest-paid NFL player only lasted about two months. The Seattle Seahawks gave Russell Wilson , making the Super Bowl XLVIII champion the richest man in the league on an average-salary basis. Wilson threw for last season.

- Contract value: $140 million (6 years)
- Average salary: $23.3 million

Despite his missing nine games in 2015, the Indianapolis Colts locked up long-term with the highest-value contract ever in the summer of 2016. Luck would miss the entire 2017 season but returned and threw for a career-best 4,593 yards in 2018, earning honors. Luck, however, when he retired one month before the start of the 2019 season.

- Contract value: $141 million (6 years)
- Average salary: $23.5 million

While the Oakland Raiders paid big money to retain Derek Carr, they reached an impasse with linebacker Khalil Mack before the 2018 season. Unable to come to terms on a new contract, the Raiders , where he became the highest-paid defensive player in NFL history. Mack has made two Pro Bowls in Chicago and tallied .

- Contract value: $150 million (5 years)
- Average salary: $30 million

Matt Ryan has never won a Super Bowl, but he holds the honor of having signed the richest contract in NFL history. In May 2018, the Atlanta Falcons, who drafted Ryan third overall in 2008, gave him Ryan has thrown for since inking his latest contract but has not led Atlanta back to the playoffs.