r/lists • Posted by Kyle 'K-Dub' Wilson🏆 Sports

Most Regrettable Free Agent Signings by NFL Teams of the Last 5 Years

Most Regrettable Free Agent Signings by NFL Teams of the Last 5 YearsAs a huge NFL fan, I've seen a lot of big-money free agent deals go south. It's tough when teams spend big, hoping for a superstar, and get a dud instead. These are the signings from the past five seasons (2021-2025 free agency periods) that really sting for the teams involved, costing them big and delivering little.
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  1. 1

    Kenny Golladay (New York Giants)

    en.wikipedia.org
    The Giants signed Golladay to a massive four-year, $72 million deal in 2021, expecting a true WR1. Unfortunately, injuries and a dramatic dip in production turned this into one of the league's biggest busts, leading to his release after just two seasons.
  2. 2

    J.C. Jackson (Los Angeles Chargers)

    en.wikipedia.org
    After being a ball-hawking corner for the Patriots, Jackson landed a five-year, $82.5 million contract with the Chargers in 2022. His tenure was plagued by injuries and significant on-field struggles, leading to him being traded back to New England in 2023.
  3. 3

    Allen Robinson (Los Angeles Rams)

    en.wikipedia.org
    Coming off a down year with the Bears in 2021, the Rams gambled on Robinson with a three-year, $46.5 million deal in 2022. He never found his form in Los Angeles, becoming an afterthought in their offense before being traded just one year into the deal.
  4. 4

    Von Miller (Buffalo Bills)

    en.wikipedia.org
    The Bills went all-in for a Super Bowl in 2022, giving Miller a six-year, $120 million contract. While he initially produced, an ACL tear, a suspension, and a reduced role in later seasons led to his eventual release in 2025, leaving a lot of dead cap.
  5. 5

    Kirk Cousins (Atlanta Falcons)

    bloggingdirty.com
    The Falcons shocked many by signing Cousins to a four-year, $180 million deal with $100 million guaranteed in 2024. The regret started almost immediately when they drafted Michael Penix Jr. eighth overall a month later, and Cousins was eventually benched and traded, with the Falcons still on the hook for some money.
  6. 6

    Christian Wilkins (Las Vegas Raiders)

    en.wikipedia.org
    The Raiders paid big for Wilkins in 2024, signing him to a four-year, $110 million contract. After only five games, he suffered a foot injury and reportedly refused further surgery, leading to a quick and costly release.
  7. 7

    La'el Collins (Cincinnati Bengals)

    en.wikipedia.org
    Hoping to solidify their offensive line, the Bengals signed Collins to a three-year, $21 million deal in 2022. He struggled significantly, especially in pass protection, and didn't provide the protection Joe Burrow desperately needed, leading to his departure.
  8. 8

    Corey Davis (New York Jets)

    en.wikipedia.org
    The Jets brought in Davis on a three-year, $37.5 million contract in 2021, but he never quite lived up to the expectations of a high-priced receiver. His inconsistent production and eventual retirement in 2023 made this a signing the Jets likely wish they could undo.
  9. 9

    Chase Edmonds (Miami Dolphins)

    en.wikipedia.org
    Miami signed Edmonds to a two-year, $12 million deal in 2022, but the move quickly backfired. He struggled to produce, averaging just 2.9 yards per carry, and was traded mid-season as part of the Bradley Chubb deal.
  10. 10

    Robert Hunt (Carolina Panthers)

    en.wikipedia.org
    In 2024, the Panthers made Hunt one of the highest-paid guards with a five-year, $100 million contract. While not a complete bust, his performance hasn't consistently matched the top-tier money, making it a questionable long-term investment given the early returns.

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