As NFL teams are fighting for open cap space and financial flexibility, a bad contract could quickly derail a franchise’s plan. Whether it is paying for past production or simply missing on a player’s evaluation, every team is guilty of handing out a bad deal that they wish they could take back.
Heading into the 2025 season, several deals stand out as very damaging. These five players are either simply not living up to the price tag or were paid far above their market value to begin with.
NFL Power Rankings: Ranking the worst contracts in the league
5. Dak Prescott, QB, Dallas Cowboys
Dak Prescott is a good quarterback, maybe even a top 10 quarterback depending on who you ask. However, he currently holds the title of the league’s highest-paid QB, even after other better quarterbacks got paid. While Prescott has been reliable in Dallas, the money paid has not translated to playoff success. This is a clear case of overpaying a good player just to keep him in the building.
4. Milton Williams, DT, New England Patriots
Williams had a breakout year in 2024, which helped him cash in during free agency. But the Patriots shocked the league with a massive $26 million annual deal, making him the second-highest paid defensive tackle in football. Despite the solid 2024 year, Williams has only one year with over 5 sacks and has started only 19 of 67 games. The Patriots did enter the offseason with boat loads of cash, but there is a chance this risk does not pay off.
3. Jawaan Taylor, OT, Kansas City Chiefs
Taylor has frankly not been good with Kansas City. Over the past two seasons, he has allowed 12 sacks and committed 37 penalties, which has made him a bit of a liability at right tackle. Despite his poor play, he's still the fifth highest-paid player at his position, making only $2 million less annually than elite tackle Zach Tom. The Chiefs are simply overpaying a player for very subpar results.
2. Kirk Cousins, QB, Atlanta Falcons
Cousins signed a big deal in 2024, only to get benched late into the 2024 season in favor of rookie Michael Penix Jr. His play was not up to par early in the year and never improved, making his $45 annual contract a horrible deal. Now he enters 2025 as a backup, and his deal looks like a complete misfire from a newer staff. Now the Falcons might be forced to find a trade just to escape the massive cap hit.
1. Deshaun Watson, QB, Cleveland Browns
The trade for Watson was already risky, but then giving him a fully guaranteed contract was just outright dumb. Years later, it is safe to say it completely backfired. Watson struggles with injury and when he does play he has not been good at all. Now dealing with an injury and the Browns heading in a new direction, it appears that Watson may be looking for a new squad very soon.