5 NFL teams that instantly regretted signing a player to a big contract

When the NFL offseason comes about, fans across the league speculate who their favorite team will be acquiring for the upcoming season and how much it’ll cost them. The financial element comes into play, too, when superstars are due a contract extension, and general managers have to determine how much they can afford to spend on key players.

Plenty of massive contracts have been handed out in recent times across the NFL, including Patrick Mahomes’ 10-year $503 million contract, but we’re sure the Kansas City Chiefs have no regrets about that deal.

However, plenty of teams across the NFL have splashed the cash, only for it to blow up in their face. Here are five such cases.

#5 - Jacksonville Jaguars and Nick Foles

Los Angeles Chargers v Jacksonville Jaguars

After leading the Philadelphia Eagles to their first Super Bowl ring, a game in which he won Super Bowl MVP, quarterback Nick Foles was hot property when he hit the open market following the conclusion of the 2018 NFL season.

The Jacksonville Jaguars picked him up, signing him to a four-year, $88 million contract with $50 million guaranteed. Foles struggled with injuries during his one season in Jacksonville, only starting four NFL games and losing them all.

What made matters worse was that when he finally returned from injury, he was benched in favor of sixth-round draft pick Gardner Minshew.

Foles was eventually traded to the Chicago Bears after the 2019 season, just a year into his four-year deal.

#4 - Seattle Seahawks and Matt Flynn

Tennessee Titans v Seattle Seahawks

The Seattle Seahawks picked up quarterback Matt Flynn in free agency in 2012 to a three-year deal worth $20.5 million, with $9 million guaranteed. The issue, however, was that the same year the Seahawks drafted Russell Wilson in the third round of the NFL Draft, and Wilson beat out Flynn as the starter before the season had even got underway.

Flynn threw just nine passes all year and was traded to the Oakland Raiders after a single season in Seattle.

#3 - Chicago Bears and Jay Cutler

Washington Redskins v Chicago Bears

Jay Culter signed a contract extension with the Chicago Bears before the 2014 season, which would see him with the team through 2020. The contract was worth $126 million, with $56 million guaranteed, but Cutler's play didn't warrant anywhere near that.

The year he signed the contract, Cutler led the league in interceptions. The Bears never won more than six games over the next three years with him as the starter. Chicago bought out Cutler's contract and released him in 2017, four years before the deal was due to expire.

#2 - Las Vegas Raiders and Jon Gruden

Chicago Bears v Las Vegas Raiders

Head coach Jon Gruden had previously managed the Oakland Raiders before the team re-acquired him in 2018. Gruden had been out of the league for several years, having spent time as a TV analyst, but that didn't stop the Raiders from signing him to a 10-year, $100 million contract.

Gruden went 4-12 in his first year back and left his role in 2021 after emails in which he had used "racist, misogynistic and homophobic" language were leaked.

#1 - Washington Redskins and Albert Haynesworth

Denver Broncos v Washington Redskins

Defensive tackle Albert Haynesworth is up there with the most regretful contract signings of all time. He signed a seven-year, $100 million contract ($41 million guaranteed) with the Washington Redskins in 2009, which proved to be a terrible bit of business.

Haynesworth showed up to camp out of shape and refused to participate in off-season workouts. His play on the field didn't warrant any special attention either.

In two seasons with Washington, he could only muster 6.5 sacks before being traded to the New England Patriots for a fifth-round draft pick in July 2011. He went down as arguably the worst free-agent signing in NFL history.