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From Dak Prescott to Deshaun Watson: The worst NFL contracts that cripple teams

Why some NFL contracts are team nightmares

Dak Prescott (Cowboys), Deshaun Watson (Browns) and Kirk Cousins...
Dak Prescott (Cowboys), Deshaun Watson (Browns) and Kirk Cousins (Falcons).LAPRESSE
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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.

Jerry Jones sarcastically criticises Dak Prescott

Deshaun Watson - Cleveland Browns

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 ing 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.

Dak Prescott - Dallas Cowboys

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.

Kirk Cousins - Atlanta Falcons

Contract: 4 years, $180 million

g 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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Von Miller - Buffalo Bills

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.

Deebo Samuel - San Francisco 49ers

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.

Miles Sanders - Carolina Panthers

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 sur 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.

Trevor Lawrence - Jacksonville Jaguars

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.

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