25 Worst NFL Free Agency Contracts Of The Past 20 Years
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Ever since the NFL started to impose the salary cap a quarter-century ago, teams that have found themselves “winning” free agency have gone on to struggle the following season. It’s been repeated over and over again. It’s in this that I look at the 25 words NFL free-agent contracts of the past two decades. Beware, Redskins fans, your team is on this list far too often.

Nick Foles, quarterback, Jacksonville Jaguars (2019)

Nov 24, 2019; Nashville, TN, USA; Jacksonville Jaguars quarterback Nick Foles (7) rushes against Tennessee Titans cornerback Logan Ryan (26) during the second half at Nissan Stadium. Mandatory Credit: Jim Brown-USA TODAY Sports

When Jacksonville signed Foles to a four-year, $88 million deal last year, it made some sense. Blake Bortles was not the answer under center. While $22 million annually seemed like a gross overpay for a career backup, it was the going market for a player these Jaguars had pegged as a starter.

Within his first several snaps as a member of the Jags, Foles suffered a clavicle injury that forced him on to injured reserve. Once he did return in mid-November, it became clear that he was not the solution in Duval. Rookie Gardner Minshew reclaimed the starting job. Foles was sent to the bench having thrown three touchdowns in parts of four games. He’s now in Chicago after a trade with the Bears back in March. What a horrible free-agent signing this proved to be.

Jeff Garcia, quarterback, Cleveland Browns (2004)

Browns Jeff Garcia
CLEVELAND – NOVEMBER 21: Quarterback Jeff Garcia #5 of the Cleveland Browns attempts to avoid the grasp of linebacker Eric Barton #50 of the New York Jets as guard Joaquin Gonzalez #73 provides additional protection at Cleveland Browns Stadium on November 21, 2004 in Cleveland, Ohio. The Jets defeated the Browns 10-7. (Photo by George Gojkovich/Getty Images)

A former Canadian Football League star and undrafted free agent of the San Francisco 49ers, Garcia had a ton of success in Northern California. He earned a Pro Bowl trip in his first three seasons replacing Steve Young under center. He also led San Francisco to consecutive playoff appearances before taking a step back in 2003.

Despite this, a downtrodden Browns organization that was still looking to find relevance after re-entering the league decided to sign Garcia to a four-year, $25 million contract. Garcia would go on to post a 3-7 record in 10 starts during the 2004 season before Cleveland released him. He ultimately put up decent seasons in Philadelphia and Tampa Bay, proving that the quarterback curse in Cleveland was real.

David Boston, wide receiver, San Diego Chargers (2003)

David Boston is tackled
SAN DIEGO – SEPTEMBER 21: Wide receiver David Boston #89 of the San Diego Chargers is tackled after making a catch against the Baltimore Ravens on September 21, 2003 at Qualcomm Stadium in San Diego, California. The Ravens defeated the Chargers 24-10. (Photo by Donald Miralle/Getty Images)

One of the many free-agent flubs of the Chargers earlier this century, the signing of Boston seemed to make sense on the surface. This former first-round pick was one year removed from leading the NFL with 1,598 receiving yards en route to an All-Pro performance.

In no way did it pan out. Even with Drew Brees tossing him the rock for the majority of the 2003 season, Boston put up less than 900 yards. This came after he signed a seven-year, $47.4 million deal. Boston was one-and-done in San Diego after suffering what would be a career-altering knee injury. Taking into account inflation, Boston’s contract was worth nearly $67 million in 2020 dollars. That’s just insane to think about.

DeMarco Murray, running back, Philadelphia Eagles (2015)

Eagles DeMarco Murray
FOXBORO, MA – DECEMBER 06: DeMarco Murray #29 of the Philadelphia Eagles runs with the ball during the game against the New England Patriots at Gillette Stadium on December 6, 2015 in Foxboro, Massachusetts. (Photo by Jim Rogash/Getty Images)

One of many modern NFL teams to realize (too late) that investing on a running back is foolish, Philadelphia inked Murray to a five-year, $40 million contract in an attempt to one-up his former Dallas Cowboys team. This came one season after Murray led the NFL in rush attempts, rushing yards, rushing touchdowns and total yards.

It proved to be an unmitigated disaster for the Eagles. Still in the prime of his career, Murray gained 702 rushing yards in his only season with Philadelphia. Making this contract even more ridiculous is the fact that Murray’s average annual salary of $8 million would rank sixth among running backs today.

Nnamdi Asomugha, cornerback, Philadelphia Eagles (2011)

Eagles Nnamdi Asomugha Falcons Julio Jones
PHILADELPHIA, PA – OCTOBER 28: Wide receiver Julio Jones #11 of the Atlanta Falcons catches a pass for a second quarter touchdown in front of cornerback Nnamdi Asomugha #24 of the Philadelphia Eagles at Lincoln Financial Field on October 28, 2012 in Philadelphia, Pennsylvania. (Photo by Rob Carr/Getty Images)

You will find several NFC East teams on this list. They like to spend in free agency. Never was this more true than when Philadelphia inked this former Oakland Raiders shutdown corner to a five-year, $60 million deal back in 2011. At the time, he was the highest-paid cornerback in NFL history. Asomugha responded by putting up four interceptions in 32 games with the team. He was burnt on a consistent basis before the Eagles decided to pull the plug on this failed experiment.

Elvis Grbac, quarterback, Baltimore Ravens (2001)

Ravens Elvis Grbac one of the worst NFL free agency deals of all time
02 Dec 2001 : Elvis Grbac of the Baltimore Ravens during the game against the Indianapolis Colts at PSINet Stadium in Baltimore, Maryland. The Ravens defeated the Colts 39-27. DIGITAL IMAGE. Mandatory Credit: Doug Pensinger/Allsport

A former eighth-round pick (that was a thing) of the 49ers back in 1993, Grbac turned nine career starts with San Francisco into a big-money gig with the Kansas City Chiefs. The Michigan product ultimately had some success in Missouri, throwing 66 touchdowns in four seasons. Though, he never lived up to the billing of a franchise guy. That did not deter Baltimore from inking Grbac to a five-year, $30 million deal in 2001. He ended up throwing 15 touchdowns compared to 18 interceptions in his only season with the team. Grbac retired from the NFL after collecting that final big check. Swindle god.

LaVar Arrington, linebacker, New York Giants (2006)

Giants LaVar Arrington
New York Giants linebacker LaVar Arrington. The Indianapolis Colts beat the New York Giants by a Score of 26 to 21 at Giants Stadium, The Meadowlands, East Rutherford, NJ., September 10, 2006. (Photo by Rich Gabrielson/NFLPhotoLibrary)

Seen as a generational talent coming out of Penn State back in 2000, there’s a reason Washington selected him No. 2 overall that April. He was an elite pass-rush threat with an ability to drop back in coverage. Initially, Arrington panned out on D.C. He earned three consecutive Pro Bowl nods for the team before an injury-plagued final two seasons in the nation’s capital. For some reason, New York then figured it made sense to sign the linebacker to a seven-year, $49 million contract. Arrington played a mere five games with the team before retiring due to injury concerns. Taking into account inflation, Arrington’s overall contract value was nearly $63 million in 2020 dollars. Ouch.

Mike Glennon, quarterback, Chicago Bears (2017)

Bears quarterback Mike Glennon was atrocious in return to Tampa Bay. Butterfinger
Sep 17, 2017; Tampa, FL, USA; Chicago Bears quarterback Mike Glennon (8) greets his teammates before the start the of a game against the Tampa Bay Buccaneers at Raymond James Stadium. Mandatory Credit: Jonathan Dyer-USA TODAY Sports

The spring of 2017 was a complete and utter mess for Bears general manager Ryan Pace. First, he decided to sign this veteran backup to a three-year deal that paid him $15 million annually. Glennon had thrown 30 touchdowns in four NFL seasons up to that point. Glennon went on to throw four touchdowns in four starts in his only season with Chicago. A side note here. Chicago also exhausted multiple draft picks that April to move up one spot for Mitchell Trubisky. What did that get them? Nothing less than having to trade for Nick Foles in 2020.

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Josh Norman, cornerback, Washington Redskins (2016)

Mike Tolbert
Dec 19, 2016; Landover, MD, USA; Carolina Panthers fullback Mike Tolbert (35) carries the ball as Washington Redskins cornerback Josh Norman (24) attempts the tackle in the fourth quarter at FedEx Field. The Panthers won 26-15. Mandatory Credit: Geoff Burke-USA TODAY Sports

Ouch. When the Carolina Panthers decided to rescind the franchise tag they had placed on Norman following a breakout 2015 campaign, it should have acted as a warning for then-front office head Bruce Allen in D.C. Instead, Allen handed Norman a five-year, $75 million contract. This made him the highest-paid corner in the NFL. Norman responded by putting up four disastrous seasons in the nation’s capital. That culminated in Pro Football Focus grading Norman out as the fifth-worst corners among 119 qualified candidates in 2019. He has since been released. Way to admit your mistake four years after the fact.

Kirk Cousins, quarterback, Minnesota Vikings (2018)

Vikings Kirk Cousins
Jan 5, 2020; New Orleans, Louisiana, USA; Minnesota Vikings quarterback Kirk Cousins (8) throws a pass against the New Orleans Saints during the second quarter of a NFC Wild Card playoff football game at the Mercedes-Benz Superdome. Mandatory Credit: John David Mercer-USA TODAY Sports

Is Cousins an above-average quarterback? His stats point in that direction. Is he worth $84 million fully guaranteed over three seasons? In no world can someone legitimately make that argument. Despite this, the former Redskins Pro Bowler earned said deal with Minnesota back in 2018. He responded by leading these Vikings to an historically bad offensive performance in January’s NFC Divisional Playoffs against the San Francisco 49ers. The backdrop here was a rift with star receiver Stefon Diggs, which led to him being traded. What did Minnesota do from there? Well, reward Cousins with another deal — this time on a two-year, $66 million extension. Fun times in Minneapolis.

Brock Osweiler, quarterback, Houston Texans (2016)

Jan 1, 2017; Nashville, TN, USA; Houston Texans quarterback Brock Osweiler (17) talks with head coach Bill O’Brien in the first half against the Tennessee Titans at Nissan Stadium. Mandatory Credit: Jim Brown-USA TODAY Sports

This could be the single-worst free-agent signing in the modern history of professional sports. That is not hyperbole. Houston gave Osweiler, a former second-round pick of the Denver Broncos, an absurd four-year, $72 million contract ahead of the 2016 season. This came after he threw 10 touchdowns in seven games as a starter for Denver the previous year. Osweiler responded by tossing one more interception (16) than touchdowns (15) in his only season with the Texans. In the end, they had to include a second-round pick to ship Osweiler and his contract to Cleveland the following spring. Seriously, Houston had to include a second-round pick to rid itself of this quarterback.

Fred Smoot, cornerback, Minnesota Vikings (2005)

Vikings cornerback Fred Smoot roasted by Panthers receiver Steve Smith
CHARLOTTE, NC – OCTOBER 30: Steve Smith #89 of the Carolina Panthers runs with the ball after catching a pass in front of Fred Smoot #27 of the Minnesota Vikings on October 30, 2005 at Bank of America Stadium in Charlotte, North Carolina. The Panthers defeated the Vikings 38-13. (Photo by Joe Robbins/Getty Images)

Party boat time. The six-year, $34 million deal Minnesota signed Smoot to back in 2005 was among one of the most foolish deals in recent decades. That doesn’t even take into account what was then the biggest scandal in recent NFL history. Smoot had not even earned as much as a Pro Bowl appearance in four seasons with Washington ahead of signing this deal. He played two miserable seasons in Minnesota before being released. All said, he started 19 games during his time in Minneapolis. The total value of this deal was over $10 million per season when taking into account inflation. Craziness.

Nate Solder, offensive tackle, New York Giants (2018)

Sep 22, 2019; Tampa, FL, USA;New York Giants offensive tackle Nate Solder (76) blocks during the second half at Raymond James Stadium. Mandatory Credit: Kim Klement-USA TODAY Sports

A product of all-time great quarterback Tom Brady during his seven seasons in New England, Solder did not earn a single Pro Bowl appearance during this span. Desperate to find protection for the aging Eli Manning ahead of the 2018 season, New York inked the overrated tackle to a four-year, $62 million contract. While he remains the Giants’ left tackle to this day, Solder is now one of the worst pass-protecting players at his position. It goes to show you that overpaying for a castoff at an important position likely won’t pan out. There’s a reason that the other team let him go.

Adam Archuleta, safety, Washington Redskins (2006)

Redskins Adam Archuleta
FOXBOROUGH, MA – AUGUST 26: Washington Redskins Adam Archuleta #40 tackles New England patriots Kevin Faulk #33 during the first half of a preseason game at Gillette Stadium August 25, 2006 in Foxborough, Massachusetts. The Patriots lead 20 to 0 at the end of the first half. (Photo by Brendan Smialowski/Getty Images)

This dude played exceedingly well during his five-year stint with the then St. Louis Rams. The former first-round pick was a borderline Pro Bowler during his time in Missouri. Something changed after he inked a seven-year, $35 million contract with the Washington Redskins. Archuleta was a shell of his former self in one season in the nation’s capital. He was released after starting just one game that year and played just one more season in the NFL before calling it quits a rich man.

Albert Haynesworth, defensive tackle, Washington Redskins (2009)

Redskins free agency bust Albert Haynesworth
LANDOVER, MD – SEPTEMBER 20: Albert Haynesworth #92 of the Washington Redskins blocks against Jacob Bell #63 of the St. Louis Rams at FedEx Field on September 20, 2009 in Landover, Maryland. (Photo by Scott Cunningham/Getty Images)

Hey, hey, hey, Fat Albert. It’s absolutely absurd how much money Washington handed Haynesworth back in 2009 after he earned two All-Pro honors in his seven seasons with the Titans. Conditioning issues already started to pop up in Nashville. That was magnified after he signed a seven-year, $100 million deal to play in D.C. Haynesworth, already north of 300 pounds, played 20 games in two seasons with the Redskins. He recorded 6.5 total sacks before being shipped off from the nation’s capital quicker than an ethical politician. All said, this contract would be worth $121.6 million in 2020 dollars. That’s just criminal.

Jerick McKinnon, running back, San Francisco 49ers (2018)

Aug 9, 2018; Santa Clara, CA, USA; San Francisco 49ers running back Jerick McKinnon (28) escapes Dallas Cowboys defensive end Tyrone Crawford (98) before being tackles by cornerback Byron Jones (31) during the first quarter at Levi’s Stadium. Mandatory Credit: Kelley L Cox-USA TODAY Sports

When the 49ers signed McKinnon to a four-year, $30 million contract back in 2018, it didn’t seem to make too much sense on the surface. Here’s a dude who averaged 3.8 yards per rush his final season with the Minnesota Vikings.

He had not even been a full-time starter throughout his four-year career in Minnesota. Like clockwork, this signing proved to be one of the biggest black eyes for 49ers general manager John Lynch. McKinnon has not suited up in a single regular-season game in San Francisco after suffering a torn ACL in the summer of 2018. While the 49ers were able to restructure McKinnon’s contract, it remains one of the worst free-agent signings in franchise history.

Le’Veon Bell, running back, New York Jets (2018)

Sep 8, 2019; East Rutherford, NJ, USA; New York Jets running back Le’Veon Bell (26) rushes against Buffalo Bills defenders during the second half at MetLife Stadium. Mandatory Credit: Noah K. Murray-USA TODAY Sports

Bell’s decision to holdout throughout the 2018 season while in a contract stalemate in Pittsburgh was already questionable. Despite this, the Jets decided to sign the former All-Pro back to an absurd four-year, $52.5 million deal last offseason. In no way did this pan out. Jets head coach Adam Gase was not a fan of signing Bell in the first place. It resulted in one of the game’s best backs averaging 3.2 yards per rush while putting up less than 800 yards on the ground. This is the most-recent example of a team valuing a running back at a much higher clip than the market suggests.

Jairus Byrd, safety, New Orleans Saints (2014)

Saints Jairus Byrd
NEW ORLEANS, LA – NOVEMBER 01: Odell Beckham #13 of the New York Giants catches a touchdown in front of Jairus Byrd #31 of the New Orleans Saints during the third quarter of a game at the Mercedes-Benz Superdome on November 1, 2015 in New Orleans, Louisiana. (Photo by Sean Gardner/Getty Images)

Ouch. Byrd had earned consecutive Pro Bowl appearances as a member of the Bills in the two years leading up to free agency. He was a highly sought-after defender in free agency that March. It’s in this that New Orleans inked him to a hefty six-year, $52.5 million contract, making Byrd one of the highest-paid defensive backs in the game. He responded by recording three interceptions in 32 games over the course of three seasons in the Bayou. This was one of the few misses for respected Saints general manager Mickey Loomis.

Trumaine Johnson, cornerback, New York Jets (2018)

Dec 9, 2018; Orchard Park, NY, USA; New York Jets cornerback Trumaine Johnson (22) walks off the field following the game against the Buffalo Bills at New Era Field. Mandatory Credit: Rich Barnes-USA TODAY Sports

A former mid-round pick from from Montana, Johnson was just a couple seasons removed from a seven-interception performance when he hit the free-agent market. While his game had regressed some in recent years, there was a strong market for the 6-foot-2 corner. New York responded by handing him the richest contract for a corner in NFL history at $72.5 million over five seasons. He responded by appearing in a combined 17 games in two seasons with the Jets prior to them releasing him this spring. They took a ridiculous $12 million dead cap hit to exile Johnson from Jersey quicker than a Trump hotel.

Michael Johnson, EDGE, Tampa Bay Buccaneers (2015)

Buccaneers Michael Johnson
Oct 5, 2014; New Orleans, LA, USA; Tampa Bay Buccaneers defensive end Michael Johnson (90) walks off the field after the New Orleans Saints scored a touchdown in overtime at the Mercedes-Benz Superdome to win 37-31. Mandatory Credit: Chuck Cook-USA TODAY Sports

Johnson had varying levels of success in his five seasons with the Bengals, recording a combined 21 sacks in his final three seasons. But outside of an 11.5-sack performance in 2012, he never really stood out as a top-end edge rusher. Despite this, Tampa Bay handed the veteran a five-year, $43.75 million free-agent deal in 2015. Johnson responded by playing just one season with the Buccaneers, recording 3.5 sacks in a part-time basis. He earned $16 million in cold hard cash before Tampa released him. Interestingly enough, Johnson would respond by putting up 13.5 sacks his next three seasons in Cincinnati.

Matt Flynn, quarterback, Seattle Seahawks (2012)

Seahawks Matt Flynn
SEATTLE, WA – DECEMBER 09: Quarterback Matt Flynn #15 of Seattle Seahawks throws in the third quarter against the Arizona Cardinals at CenturyLink Field on December 9, 2012 in Seattle, Washington. (Photo by Kevin Casey/Getty Images)

Seattle had no way to know that then-rookie third-round pick Russell Wilson would turn into one of the best quarterbacks in modern NFL history back in 2012. Even then, the idea of handing a career backup in Flynn $19.5 million over three seasons made no sense. Flynn had started two games in four seasons with Green Bay. The end result here was the former LSU quarterback attempting nine passes in his only year in Seattle, making a cool $8 million in the process. This swindle god called it quits on his career following the 2014 season after earning a cool $19.2 million. He started a total of seven games.

Sam Bradford, quarterback, Arizona Cardinals (2018)

September 16, 2018; Los Angeles, CA, USA; Arizona Cardinals quarterback Sam Bradford (9) drops back to pass against the Los Angeles Rams during the first half at the Los Angeles Memorial Coliseum. Mandatory Credit: Gary A. Vasquez-USA TODAY Sports

Arizona was stuck between a rock and a hard place heading into the 2018 season. It knew that Bradford’s best days were behind him. But without many options to speak of, general manager Steve Keim and Co. signed him to a one-year, $20 million contract. Not a horrible overall contract. Unfortunately, Bradford played in just three games that season before suffering what would end up being a career-ending injury. He made nearly $16 million in cold-hard cash, a clear example that the contract was structured in a way that wasn’t beneficial to the team.

Martellus Bennett, tight end, Green Bay Packers (2017)

The Packershave released Martellus Bennett
Sep 28, 2017; Green Bay, WI, USA; Green Bay Packers tight end Martellus Bennett (80) is shown during the fourth quarter of their game against the Chicago Bears at Lambeau Field. Mandatory Credit: Mark Hoffman/Milwaukee Journal Sentinel via USA TODAY NETWORK

Strange. That’s the best way to describe Bennett’s sole season with the Pack. He signed a three-year, $21 million contract two tremendous seasons with the division-rival Bears. After just seven games, Bennett was released following a beef with Green Bay’s front office. It is believed he failed to disclose an injury ahead of signing with the team. In turn, Bennett was turned off. It led to a hastily arranged divorce and one of the worst free-agent signings in modern Packers history. Bennett earned about $1 million for each game he suited up in Wisconsin.

Deion Sanders, cornerback, Washington Redskins (2000)

Redskins Deion Sanders
CLEVELAND, OH – AUGUST 19: Deion Sanders #21 of the Washington Redskins prays before a preseason game against the Cleveland Browns at Cleveland Browns Stadium on August 19, 2000 in Cleveland, Ohio. The Redskins defeated the Browns 24-0. (Photo by Joe Robbins/Getty Images)

Entering his 12th season in the league, a then 32-year-old Sanders was already a shell of his former self. The future Hall of Famer did earn a Pro Bowl appearance in Dallas the season prior, but he was nowhere near the shutdown guy we saw in both Big D and San Francisco earlier. It’s in this that Washington’s decision to hand Prime Time a seven-year, $56 million contract backfired big time. He did record four interceptions in his only season in D.C., but found himself burnt more often than not. Sanders would ultimately retire following the season, only to return to the NFL as a member of the Ravens three years later. The Skins ruined him.

Javon Walker, wide receiver, Oakland Raiders (2008)

Raiders Javon Walker was an NFL free agency bust
October 19, 2008: Oakland Raiders wide receiver Javon Walker #84 catches ball and works to outrun New York Jets safety Eric Smith #33 on Sunday, October 19, 2008 at McAfee Coliseum in Oakland, California. The Raiders defeated the Jets 16-13. (Photo by Al Golub/Icon Sportswire/Corbis/Icon Sportswire via Getty Images)

This Florida State product had all of the looks of a true No. 1 receiver during the latter part of his days with the Green Bay Packers and in Denver. In fact, Walker put up nearly 1,100 yards back in 2006. Unfortunately, Oakland lost the memo that included him missing half of the 2007 season before signing Walker to a six-year, $55 million contract. Like so many Raiders signings during that time, it backfired big time. Walker was never himself in Northern California, recording 15 catches in 11 combined games before said injuries forced him to hang up his cleats. This remains one of the worst free-agent signings of the past two decades.

Vincent Frank
Editor here at Sportsnaut. Contributor at Forbes. Previous bylines include Bleacher Report, Yahoo!, SB Nation. Heard on ESPN Radio and NBC Sports Radio. Northern California native living it up in Las Vegas. The Keto lifestyle. Traveler. Reader. TV watcher. Dog daddy. Sam Malone = greatest TV character ever. "Carpe diem. Seize the day, boys. Make your lives extraordinary," John Keating.