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BigPaulSports > Blog > Game Analysis > Money not well spent: Ranking 12 worst NFL free-agent signings of 21st century
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Money not well spent: Ranking 12 worst NFL free-agent signings of 21st century

BigP
Last updated: 2025/03/10 at 3:26 PM
BigP Published March 10, 2025
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Money not well spent: Ranking 12 worst NFL free-agent signings of 21st century
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11. WR Javon Walker, 2008 (Six-year, $55M deal with the Oakland Raiders)5. OT Trent Brown, 2019 (Four-year, $66M deal with the Oakland Raiders)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)

NFL free agency officially begins Wednesday at 4 p.m. ET, but teams can negotiate with the agents of players they’re interested in starting Monday at 12 p.m. ET.

One of the best free-agent signings in NFL history came just last offseason when Saquon Barkley inked a three-year, $37.8 million deal with the Philadelphia Eagles. 

But for every great signing, there’s another that didn’t pan out. And in some cases, it turned into a full-fledged disaster. 

That said, here are the 12 worst NFL free-agent signings of the 21st century.

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Note: This is a list of players who signed a contract with a new team in free agency. Players who re-signed with their respective team or were traded to a team and subsequently signed an extension with that team are not included.

The Jets brought in Bell, a two-time All-Pro and three-time Pro Bowler, to be a featured part of their offense and take some pressure off then-second-year quarterback Sam Darnold. It didn’t go according to plan. After not playing in 2018 due to a contract dispute with Pittsburgh, Bell averaged a then-career-low 3.2 yards per carry in his debut season with New York (2019). Despite totaling a combined 1,250 yards from scrimmage (789 rushing and 461 receiving) that year, Bell didn’t provide the spark the Jets had hoped for, and he was released during the 2020 season.

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

Oakland took a chance on Walker, a first-round draft pick by Green Bay in 2002, being a difference-maker in their passing attack, and things simply didn’t work out. A former Pro Bowler who surpassed 1,000 receiving yards in both 2004 and 2006, Walker was held back by injury in the first two years of his deal with the Raiders and struggled mightily in the games he did play in, logging just 15 receptions over 11 games. He was released after the 2009 season.

In an offseason that saw the Broncos most notably acquire veteran quarterback Russell Wilson, they also added Gregory, foreseeing an ascending player making an impact on their defense off the edge. Unfortunately, Gregory appeared in just six games in 2022 due to a knee injury, logging three sacks in two seasons. He was waived in 2023.

Detroit wanted to improve its pass rush and identified Flowers — who played under then-Lions head coach Matt Patricia when he was the defensive coordinator in New England — as a player who would make a difference. Flowers totaled seven sacks and two forced fumbles in his first season with Detroit (2019), which was in line with his then-career production. However, he went on to appear in a combined 14 games from 2020-21 due to shoulder and knee issues and totaled just 3.5 sacks over that span. The Lions subsequently released Flowers in the 2022 offseason.

After a 2014 campaign which saw Murray rush for 13 touchdowns and a league-high 1,845 yards — which still stands as Dallas‘ franchise record — the Cowboys let him depart for the NFC-rival Eagles; Murray did not build on his historic 2014 season and back-to-back 1,000-yard campaigns. In 15 regular-season games with Philadelphia in 2015, Murray rushed for a career-low 3.6 yards per carry and was traded to Tennessee in the 2016 offseason. To make matters worse for the Eagles, Murray was a Pro Bowler in his first season with the Titans.

The Giants needed a left tackle, and they signed arguably the best one available in the 2018 offseason. That said, while he only missed one game (Solder opted out of the 2020 season due to COVID-19), Solder’s four-year stint in New York was a disappointment, as the team struggled to keep quarterbacks Eli Manning and Daniel Jones upright and continued to seek solutions up front. Solder was inconsistent in pass protection and didn’t play like the rock that he was previously for the Patriots.

After being blanked at home 30-0 in the wild-card round by Kansas City, Houston showed Osweiler the bag after he helped the Broncos go 5-2 in place of an injured Peyton Manning in 2015. The Texans did win the AFC South and then a wild-card round playoff game in 2016, but Osweiler was benched at one point during the regular season, finishing with more interceptions (16) than touchdowns (15) and a mere 72.2 passer rating. Houston traded him and a second- and sixth-round draft pick to Cleveland for a fourth-rounder in the ensuing offseason.

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

The Raiders wanted a tackle to keep quarterback Derek Carr on his feet, and Brown did just that for Tom Brady and the Patriots in the 2018 season, which saw them win Super Bowl LIII. While Brown was a Pro Bowler in his first season with the Raiders (2019), he appeared in just 11 games and then five games in 2020 due to a calf injury, among other issues. The Raiders traded Brown back to the Patriots in the 2021 offseason.

Sensing a theme with when the worst contracts were signed? One year after helping the Eagles win Super Bowl LII in place of an injured Carson Wentz — and helping them win a playoff game again in 2018 — the Jags brought in Foles to be their long-term answer under center. However, Foles suffered a broken clavicle in his first game with Jacksonville, and the team went 0-4 in the starts that he made in 2019. The Jags traded him to Chicago in the 2020 offseason.

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

The Giants thought they were a team on the rise in 2021 and brought in Golladay, who was coming off an injury-riddled 2020 campaign, to be their No. 1 receiver. It didn’t go the way they envisioned. In his first season with the Giants (2021), Golladay — who surpassed 1,000 receiving yards in both 2018 and 2019 with the Lions — had just 37 receptions and didn’t record a single touchdown. Furthermore, Golladay had just 43 receptions and one touchdown in two seasons with the Giants, who released him after the 2022 season.

This is a creative one. The Falcons signed then-35-year-old Cousins, who was coming off suffering a torn Achilles tendon in the 2023 season, to a massive deal and then drafted quarterback and 2023 Heisman Trophy finalist Michael Penix Jr. with the eighth overall pick in the 2024 NFL Draft. In what was an up-and-down experience, Atlanta went 7-7 with Cousins, a four-time Pro Bowler, in 2024 before benching the veteran for Penix. Atlanta still missed the playoffs and is now expected to either have Cousins be its backup next season or, more likely, release him altogether.

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

Haynesworth was one of the best defensive tackles of his generation with the Titans. A two-time All-Pro, Haynesworth inhaled running backs and was a nightmare for offensive lines to maintain, which is why Washington gave him such an enormous contract — but the team didn’t get what it signed up for. Across the two years that he was on Washington’s roster (2009-10), Haynesworth appeared in just 20 games, didn’t make a start in 2010 and totaled a combined 6.5 sacks, 53 combined tackles and zero forced fumbles. Washington traded Haynesworth to the Patriots in July 2011. His $14.3 million average annual salary was 11.6% of the $123 million salary cap in 2009. For perspective, had Haynesworth’s contract been inked in the 2025 offseason (the salary cap is $279.2 million for 2025) with his average annual salary accounting for the same percentage of money available under the cap, the defensive tackle would’ve been making roughly $32.4 million per season on a seven-year, $226.8 million deal.

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BigP March 10, 2025
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