Most Notorious Sports Contracts Ever Signed

Every professional sports organization employs staff who specialize in contract negotiations. Their role is to design offers that reflect a player’s past performance, future potential and prevailing market conditions. They analyze data, consult with personnel departments and spend countless hours ensuring a contract’s value aligns with the athlete’s worth. Still, errors happen, and franchises often overpay.

Mistakes are part of the job in any front office: injuries, off-field issues, questionable clauses or simply misjudging a player’s future can all turn a deal sour. While many of the worst contracts produced poor returns for teams, some deals were also bad for the athletes themselves.

Below is a curated list of some of the most notorious and ill-fated sports contracts in history, ranked and summarized for context.

100. Alex Rodriguez

Sport: Baseball (MLB) — Year: 2008 — Contract: 10 years, $275 million — Team: New York Yankees — Return: 880 G, .269 AVG, 178 HR, 583 RBI

Alex Rodriguez signed one of the largest contracts in sports history, but his tenure included a full-season suspension for PED use. A contract provision required the Yankees to pay a reduced amount during the suspension, and despite missed earnings, A-Rod still earned more than $450 million across his career.

99. Sean Avery

Sport: Hockey (NHL) — Year: 2008 — Contract: 4 years, $15.5 million — Team: Dallas Stars — Return: 23 GP, 3 G, 7 A, 10 PTS

Signed largely to add grit, Avery’s tenure imploded after controversial public comments and a suspension. Teammates resisted his return, and the club swiftly moved on.

98. Jon Koncak

Sport: Basketball (NBA) — Year: 1989 — Contract: 6 years, $13.7 million — Team: Atlanta Hawks — Return: 430 G, 3.6 PPG, 4.3 RPG

When a backup center received a huge contract in an era when most salaries were private, the deal drew national attention and even motivated future stars to seek bigger paydays.

97. Dez Bryant

Sport: Football (NFL) — Year: 2010 — Contract: 5 years, $12 million ($8.4 million guaranteed) — Team: Dallas Cowboys — Return: 75 G, 381 REC, 5,424 YDS, 56 TD

Bryant’s rookie contract included strict behavioral provisions—curfew, counseling and lifestyle restrictions—highlighting the team’s concern about maturity. Though the Cowboys later extended him to a much larger deal, disciplinary issues led to his release.

96. Todd MacCulloch

Sport: Basketball (NBA) — Year: 2001 — Contract: 6 years, $34 million — Team: New Jersey Nets — Return: 62 G, 9.7 PPG, 6.1 RPG

A backup center signed to a large multi-year contract found the offer so surprising he thought it was a joke. He lasted one season before being moved on.

95. Kevin Brown

Sport: Baseball (MLB) — Year: 1999 — Contract: 7 years, $105 million — Team: Los Angeles Dodgers — Return: 137 G, 58-32, 2.83 ERA

Brown signed baseball’s first $100 million-plus deal, including extravagant perks like charter flights for his family, creating a high-cost benchmark for future contracts.

94. Horace Grant

Sport: Basketball (NBA) — Year: 1996 — Contract: 5 years, $50 million — Team: Orlando Magic — Return: 193 G, 11.4 PPG, 8.1 RPG

Grant negotiated a front-loaded extension that paid a large share in the early years. That payroll structure limited the Magic’s flexibility and played a role in their inability to retain Shaquille O’Neal.

93. Willie Taggart

Sport: Football (NCAA) — Year: 2018 — Contract: 6 years, $30 million — Team: Florida State — Return: 21 G, 9-12 record

Florida State fired Taggart after less than two seasons and faced multiple buyouts tied to his hiring—paying more than $20 million combined to settle obligations to Taggart and prior employers.

92. Eddie Gaedel

Sport: Baseball (MLB) — Year: 1951 — Contract: 1 game, $100 — Team: St. Louis Browns — Return: 1 plate appearance, walk

Eddie Gaedel, standing 3-foot-7, was inserted as a publicity stunt and drew a walk in his lone plate appearance. MLB voided the contract after the stunt, though the plate appearance remains in the record books.

91. Nnamdi Asomugha

Sport: Football — Year: 2011 — Contract: 5 years, $60 million ($25 million guaranteed) — Team: Philadelphia Eagles — Return: 32 G, 95 TKL, 4 INT

Signed for leadership and play, Asomugha struggled in Philadelphia both on and off the field. A disastrous first season and strained locker-room relationships led to an early exit.

90. Brock Osweiler

Sport: Football — Year: 2016 — Contract: 4 years, $72 million ($37 million guaranteed) — Team: Houston Texans — Return: 15 G, 15 TD, 16 INT

Osweiler’s poor performance in Houston was so severe the team essentially paid another franchise to take him and included draft compensation to complete the trade.

89. Ilya Bryzgalov

Sport: Hockey (NHL) — Year: 2011 — Contract: 9 years, $51 million — Team: Philadelphia Flyers — Return: 99 GP, .905 SV%, 3.09 GAA

The Flyers traded for Bryzgalov and extended him to a lengthy deal that backfired quickly. They bought him out two years later, triggering a long-term payment schedule that left the organization paying millions for seasons he did not play.

88. Bret Hart

Sport: Wrestling — Year: 1997 — Contract: 3 years, $7.5 million — Promotion: WCW

Following his controversial exit from WWF, Hart signed a fully guaranteed WCW deal with substantial per-event guarantees and medical provisions. Injuries cut his in-ring career short, leaving the contract’s value underscored by limited performance.

87. Pablo Sandoval

Sport: Baseball (MLB) — Year: 2015 — Contract: 5 years, $90 million — Team: Boston Red Sox — Return: 161 G, .237 AVG, 14 HR

Sandoval arrived in Boston out of shape, struggled to produce and was cut partway through the contract, yet the team remained responsible for much of the remaining payout.

86. Andrea Pirlo

Sport: Soccer (MLS) — Year: 2015 — Contract: 3 years, $14.1 million — Team: New York City FC — Return: 60 GM, 1 G, 11 AST

Pirlo’s signing was designed to boost attendance and brand visibility. On the field, however, his contributions were limited relative to his salary.

85. Nick Foles

Sport: Football (NFL) — Year: 2019 — Contract: 4 years, $88 million ($45.1 million guaranteed) — Team: Jacksonville Jaguars — Return: 4 G, 3 TD, 2 INT

Foles’ contract included large guarantees and immediate cash payouts that led to a season in which he earned substantial sums while playing only a handful of games.

84. Rusney Castillo

Sport: Baseball (MLB) — Year: 2014 — Contract: 7 years, $72.5 million — Team: Boston Red Sox — Return: 99 G, .262 AVG, 7 HR

The Red Sox relegated Castillo to the minors to avoid luxury-tax consequences, paying his salary while preventing him from contributing at the major-league level.

83. Mike Vanderjagt

Sport: Football (NFL) — Year: 2006 — Contract: 3 years, $4.5 million ($2.5 million guaranteed) — Team: Dallas Cowboys — Return: 10 G, 72.2 FG%

The Cowboys shifted from undervaluing kickers to paying a premium and quickly regretted it when Vanderjagt underperformed and failed to meet expectations.

The list continues through a long roster of notable examples—players whose deals were undone by injuries, poor fit, misconduct, miscalculated durability or simply bad timing. Some contracts reshaped league rules, others bankrupted franchises’ plans, and a few left players regretting terms they signed. These cases underscore how complex and consequential contract decisions can be in professional sports.

From guaranteed deals that paid athletes while they sat on the bench to deferred-payment plans that paid out for decades, these contracts illustrate how financial commitments and human unpredictability collide in the world of sports.