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21st Century NFL Free-Agent Fiascos: The 12 Worst Money Misfires

Money not well spent: Ranking 12 worst NFL free-agent signings of 21st century

Money not well spent: Ranking the 12 worst NFL free-agent signings of the 21st century begins with the official kickoff of NFL free agency, set for Wednesday at 4 p.m. ET. However, teams can start negotiating with player agents as early as Monday at 12 p.m. ET, creating a flurry of activity in the league.

Last offseason, one of the most successful free-agent moves was Saquon Barkley’s three-year, $37.8 million contract with the Philadelphia Eagles. His impact on the team was significant, showcasing how effective signings can reshape a franchise.

However, for every standout signing, there are cautionary tales of contracts that went south, turning into costly mistakes for franchises. Here, they outline the 12 worst NFL free-agent signings of the 21st century.

This list focuses exclusively on players who signed with new teams during free agency. Players who re-signed with their original teams or were traded and then extended are not included.

The New York Jets made headlines by signing Le’Veon Bell, a two-time All-Pro and three-time Pro Bowler, in hopes of bolstering their offense and supporting then-second-year quarterback Sam Darnold. Unfortunately, Bell’s tenure with the Jets was underwhelming. After sitting out the 2018 season due to a contract dispute with Pittsburgh, he managed only 3.2 yards per carry in his debut season with New York in 2019. Despite accumulating 1,250 yards from scrimmage, Bell’s performance fell short of expectations, leading to his release during the 2020 season.

11. WR Javon Walker, 2008 (Six-year, $55M deal with the Oakland Raiders)

The Oakland Raiders took a gamble on Javon Walker, a former first-round pick by the Green Bay Packers, hoping he would elevate their passing game. Unfortunately, injuries plagued Walker during his initial years with the Raiders, and he could only muster 15 receptions over 11 games before being released after the 2009 season.

In a significant offseason, the Denver Broncos acquired veteran quarterback Russell Wilson and also signed Randy Gregory, anticipating he would enhance their defensive edge. Sadly, Gregory only participated in six games during the 2022 season due to a knee injury, totaling three sacks in two seasons before being waived in 2023.

The Detroit Lions sought to strengthen their pass rush by signing Trey Flowers, a player familiar to then-head coach Matt Patricia from their time in New England. Flowers had a decent first season, recording seven sacks and two forced fumbles in 2019. However, injuries limited him to just 14 games over the next two seasons, resulting in only 3.5 sacks. The Lions ultimately released him in 2022.

After a standout 2014 season where DeMarco Murray rushed for 1,845 yards, a franchise record for the Dallas Cowboys, he signed with the Philadelphia Eagles. Unfortunately, his performance dipped significantly, averaging just 3.6 yards per carry in 2015. The Eagles traded him to the Tennessee Titans the following offseason, where he regained Pro Bowl form in his first year.

The New York Giants, in desperate need of a left tackle, signed Nate Solder, considered one of the best available in the 2018 offseason. Although he only missed one game due to opting out for COVID-19, Solder’s time with the Giants was marked by inconsistency in pass protection, failing to provide the stability that was expected.

5. OT Trent Brown, 2019 (Four-year, $66M deal with the Oakland Raiders)

The Raiders aimed to protect quarterback Derek Carr by signing Trent Brown, who had excelled with the New England Patriots. Although he earned a Pro Bowl selection in his first year with the Raiders, injuries limited him to 11 games in 2019 and just five in 2020. Ultimately, the Raiders traded him back to the Patriots in 2021.

Nick Foles, who played a pivotal role in the Eagles’ Super Bowl LII victory, was signed by the Jacksonville Jaguars with hopes of securing their quarterback position. Unfortunately, he broke his clavicle in his first game and struggled in his starts, leading to a 0-4 record. He was subsequently traded to Chicago in the 2020 offseason.

3. WR Kenny Golladay, 2021 (Four-year, $72M deal with the New York Giants)

1. DT Albert Haynesworth, 2009 (Seven-year, $100M deal with Washington)

Albert Haynesworth was once regarded as one of the premier defensive tackles in the league during his time with the Tennessee Titans. His massive seven-year, $100 million contract with Washington was intended to solidify their defensive line. However, Haynesworth’s performance drastically declined, as he played only 20 games over two years, totaling just 6.5 sacks. His contract, which accounted for a staggering 11.6% of Washington’s salary cap in 2009, would equate to approximately $32.4 million per season had it been signed in 2025. Washington traded him to the Patriots in 2011, marking a significant misstep in their free-agent strategy.

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Written By

Dave Gallo is a leading sports bettor and handicapper since 1999, known for his impressive 10-0 winning streaks. A journalism, advertising, and media studies major at the University of Wisconsin-Milwaukee, he combines his betting expertise with academic knowledge. Gallo's strong work ethic and passion for sports fuel his ongoing success and scholarly pursuits.

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