In the high-stakes world of the NFL, teams gamble big money on players they believe will lead them to success. Sometimes, those gambles pay off with Super Bowl rings and sold-out stadiums. But other times, they become cautionary tales. Poor planning, overreactions to market trends, and misplaced faith in players can saddle franchises with bloated contracts that haunt their salary cap for years. Whether it’s due to injuries, underperformance, or questionable decision-making, these deals can cripple a team’s ability to build a competitive roster.
Bad contracts don’t just affect the bottom line-they ripple through the entire organization. “You’re not just overpaying one player; you’re sacrificing depth and flexibility,” said an NFL cap analyst. The worst deals often reflect desperation, where teams prioritize short-term gains or headlines over sustainable success. Let’s break down some of the most egregious examples and explore how these contracts have gone sideways for the teams involved.
Contract: 5 years, $230 million (fully guaranteed)
Desperation drove Cleveland to make Watson the first fully guaranteed $200+ million player, despite off-field controversies and inconsistent play. Since joining the Browns, his performance (81.7 QB rating) has lagged behind previous starters like Jacoby Brissett. Add his Achilles injury, and Cleveland faces $63+ million cap hits annually through 2025 with no escape hatch.
Contract: 4 years, $240 million
Dallas painted itself into a corner by franchise-tagging Prescott twice, giving him unprecedented leverage. The result? A $231 million guarantee and a $60 million annual salary-higher than anyone in NFL history. Jerry Jones may tout his business savvy, but this deal suggests otherwise. Prescott’s looming $40 million cap hit in 2025 makes it clear Dallas prioritized short-term solutions over long-term strategy.
Contract: 4 years, $180 million
Signing a 36-year-old Cousins after an Achilles tear was bold; drafting Michael Penix Jr. after committing $100 million guaranteed was baffling. “Why pay top dollar for a QB if you’re planning for the future?” critics asked. Atlanta’s mixed messaging has left fans confused and their cap strained.
Marcus Williams – Baltimore Ravens
Contract: 5 years, $70 million
Williams hasn’t justified being the league’s eighth-highest-paid safety. His $18.72 million cap hit in 2024 is a far cry from his underwhelming production. Baltimore’s defense is stretched thin, and Williams’ deal is a glaring misstep in an otherwise strong roster.
Derek Carr – New Orleans Saints
Contract: 4 years, $150 million
Carr’s conservative playing style doesn’t align with his hefty cap hits-$51.4 million in 2025 and $61.4 million in 2026. Known for salary-cap gymnastics, the Saints have tied themselves to a deal that limits their flexibility for years to come.
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Contract: 6 years, $120 million
The Bills bet on Miller for immediate impact, but injuries and age caught up quickly. His $15.1 million cap hit in 2024 feels excessive for a player benched during his comeback year. Miller’s deal is a stark reminder of the risks of overpaying aging stars.
Contract: 3 years, $71.55 million
Samuel’s $15.8 million cap hit isn’t astronomical, but his uneven usage and frustrations with the team are concerning. Cutting him would result in $31.6 million in dead money. With younger players like Brandon Aiyuk recovering from injury, Samuel’s deal feels like a financial tightrope.
Contract: 4 years, $25.4 million
Sanders might be the fourth-string running back in 2024, yet he carries a $7.7 million cap hit. Chuba Hubbard has outperformed him, and rookie Jonathon Brooks could surpass him as soon as he’s healthy. Sanders’ deal is likely to end with a release in 2025.
Joey Bosa – Los Angeles Chargers
Contract: 5 years, $135 million
Once a dominant force, Bosa’s injuries have derailed his production. Playing just 14 games over the last two seasons with nine combined sacks, his $26.1 million cap hit in 2024 feels like an anchor on the Chargers’ finances.
Contract: 5 years, $275 million
Lawrence’s $55 million annual salary doesn’t match his performance. The Jaguars hoped for MVP-level play, but inconsistency and poor coaching have left him looking average. With escalating cap hits reaching $78.5 million in 2029, Jacksonville isn’t even maximizing the deal’s early years.
These contracts show how short-sighted decisions or gambles on potential can backfire, leaving teams scrambling to manage their cap space and fans questioning their front offices.
In the NFL, contract negotiations can make or break a team’s salary cap situation. While some deals work out in a team’s favor, others can prove to be crippling. From Dak Prescott to Deshaun Watson, let’s take a look at some of the worst NFL contracts that have left teams struggling to stay competitive.
1. Dak Prescott, Dallas Cowboys: In 2021, Prescott signed a four-year, $160 million contract extension with the Cowboys, making him one of the highest-paid quarterbacks in the league. While Prescott has shown flashes of brilliance on the field, his massive contract has limited the Cowboys’ ability to build a strong supporting cast around him. With a lackluster defense and an underperforming offensive line, the Cowboys have struggled to make a deep playoff run with Prescott at the helm.
2. Deshaun Watson, Houston Texans: Watson signed a four-year, $156 million contract extension with the Texans in 2020, making him one of the highest-paid quarterbacks in the league at the time. However, Watson’s contract has become a burden for the Texans as he has demanded a trade following a tumultuous offseason. With Watson’s future in limbo and his legal troubles mounting, the Texans find themselves in a difficult position with a highly paid quarterback who may not even suit up for them in the future.
3. Carson Wentz, Philadelphia Eagles: Wentz signed a four-year, $128 million contract extension with the Eagles in 2019, but his performance on the field quickly declined. Wentz struggled with inconsistency and turnovers, eventually losing his starting job to rookie quarterback Jalen Hurts. The Eagles were forced to trade Wentz to the Indianapolis Colts in 2021, but his contract left them with a significant dead money hit against their salary cap.
Overall, these contracts serve as cautionary tales for NFL teams looking to lock up their franchise quarterbacks. While having a talented signal-caller is crucial for success in the league, overpaying for their services can have long-term repercussions on a team’s ability to build a competitive roster. As teams continue to navigate the complexities of the salary cap, it’s important to learn from the mistakes of the past and approach contract negotiations with caution.
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