With a key date looming in the 2025 NFL season, Stuff365 takes a look at seven of the worst NFL trade deadline deals.
Teams have until Tuesday, November 4, to add key pieces to their rosters, but history shows mid-season trades rarely go to plan.
Across decades of deadline chaos, front offices have panicked, overpaid, or simply hit send too late. Some of those mistakes haunted franchises for years.
Others looked promising in the moment, only for the traded player to flop before finding form somewhere else.
Here are seven of the worst NFL trade deadline deals ever.
2023 — Chase Young’s San Francisco Fade (Commanders and 49ers)
The 49ers rolled the dice on Chase Young, hoping a reunion with college teammate Nick Bosa would revive his form. It didn’t.
Young flashed early but never became a consistent threat, finishing with just 3.5 sacks before San Francisco let him walk in free agency.
Washington, meanwhile, happily moved on from another failed first-rounder.
It wasn’t a disaster for either side — just a perfect snapshot of deadline hype meeting reality.
2022 — Chase Claypool’s Chicago letdown (Steelers and Bears)
The Bears thought they were buying Justin Fields a star receiver. Instead, they bought frustration.
Chicago sent Pittsburgh a second-round pick for Claypool, who managed one touchdown and 18 quiet games before being traded again a year later.
Pittsburgh used the pick to draft Joey Porter Jr., now one of the league’s best young corners. For Chicago, it was a painful lesson in patience and valuation.
Even by deadline standards, few trades collapsed faster.
2019 — Mohamed Sanu’s vanishing act (Falcons and Patriots)
The Patriots thought they were fixing their passing game. Instead, they got eight quiet games and a regretful Bill Belichick.
New England sent Atlanta a second-round pick for Sanu midway through 2019. He caught just 26 passes, injured his ankle, and was released before the next season even started.
Atlanta used the pick to reload, while New England’s offense never found rhythm again. Belichick later admitted the deal was a mistake, calling it a “swing that didn’t connect.”
2017 — The Browns’ fax fiasco (Cleveland and Cincinnati)
Cleveland finally found a quarterback it liked. Then it forgot to hit the send button.
Moments before the 2017 trade deadline, the Browns agreed a deal with the Bengals for backup passer AJ McCarron.
Cleveland even emailed confirmation to the league office, but never submitted the official paperwork.
The clock ran out, the trade was void, and the Browns stayed winless. McCarron stayed in Cincinnati, wondering how close he’d come to NFL purgatory.
It remains one of the league’s most bizarre administrative failures.
2012 — Aqib Talib’s breakout (Buccaneers and Patriots)
Tampa Bay gave up on a star too soon.
The Buccaneers shipped Aqib Talib to New England for a fourth-round pick after growing tired of his off-field issues. The Patriots saw potential where Tampa saw a headache — and they were right.
Talib became a Pro Bowler the following season and anchored one of the league’s best secondaries before winning a Super Bowl in Denver.
Tampa’s return never amounted to much, and the deal became a masterclass in impatience. The Bucs traded away one of the best corners of the decade for loose change.
2008 — Favre’s one-year detour (Packers and Jets)
When Brett Favre left Green Bay, the breakup dominated every sports show in America.
The Jets thought they were landing a legend but the ordeal turned into a soap opera.
Favre started well, leading New York to an 8–3 record, but his arm gave out as winter hit. He threw nine interceptions over the final five games, the Jets collapsed to 9–7, and missed the playoffs.
A few months later, Favre retired (again) only to resurface in Minnesota and torment New York from afar.
Green Bay, meanwhile, handed the job to Aaron Rodgers and moved straight into another decade of stability.
1989 — The Herschel Walker Heist (Vikings and Cowboys)
The Vikings thought they were trading for a Super Bowl. Instead, they handed Dallas the keys to a dynasty.
Minnesota sent five players and six draft picks to the Cowboys for running back Herschel Walker, hoping he’d be the missing piece.
Walker struggled to fit the offense, rushed for just five touchdowns in two seasons, and was gone by 1992.
Dallas’ picks turned into Emmitt Smith, Darren Woodson, and Russell Maryland — three cornerstones of their 1990s championship teams.
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