The 10 Worst Contracts in Sports

David KenyonFeatured ColumnistMay 1, 2019

The 10 Worst Contracts in Sports

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    Gail Burton/Associated Press

    Negotiating a contract is challenging for both the individual and the front office. Teams want to pay as little as possible for the most future value, and players typically seek every possible dollar for their hard work in the past.

    Sometimes, the subsequent deal simply doesn't work out.

    Touted players might not match their billing. In other cases, an organization might overpay for a non-superstar or offer a long-term contract that turns ugly as the years elapse.

    Only current contracts in the NFL, NBA, NHL and MLB were considered, though one of those leagues didn't have a player make this list. The players who signed the deal, however, don't necessarily have to remain active.

Bobby Bonilla, New York Mets

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    Stephen Dunn/Getty Images

    Contract: $1.2 million per year through 2035

    July 1 is a much-anticipated landmark on the sports calendar because NBA free agency begins. The date also marks Bobby Bonilla Day.

    Every year from 2011 through 2035, the former New York Mets outfielder receives a deferred payment of $1,193,248.20. The agreement is the result of New York releasing him before the 2000 season and turning the remaining $5.9 million into $29.8 million.

    Sure, we could argue about the value of investing $5.8 million 20 years ago. But that's not as funny as Bonilla remaining the 20th-highest-paid player on the payroll in 2019, per Spotrac.

Miguel Cabrera, Detroit Tigers

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    Paul Sancya/Associated Press

    Contract: Eight years, $248 million (through 2023)

    Miguel Cabrera isn't the same player anymore.

    Considering how dominant he once was, that's a hugely disappointing fact. The two-time American League MVP won the Triple Crown in 2012, made 11 All-Star teams and is a career .316 hitter.

    But in 2017, Cabrera managed just 16 home runs in 529 plate appearances. Hamstring and biceps injuries limited him to 38 games in 2018, and the 36-year-old is now staring at a future of moderate effectiveness with a handful of seasons remaining on his deal.

    Not that he should, but don't expect him to apologize.

    "People can say I'm not worth this contract," he said, per Bob Nightengale of USA Today. "They can say whatever they want, really. But they're not going to hurt my feelings. I'm not going to apologize. Why should anyone be sorry? I don't see any teams losing money. They all have it."

Chris Davis, Baltimore Orioles

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    Gail Burton/Associated Press

    Contract: Seven years, $161 million (through 2022)

    The Baltimore Orioles extended this lucrative deal to Chris Davis because of his outstanding power. The left-handed batter walloped 159 home runs from 2012 through 2015.

    However, strikeouts were always prevalent. During that four-year stretch, he had 749 strikeouts and only 253 walks. Davis at least atoned for the whiffs with a .256 batting average and 0.876 OPS―more than enough to appreciate his power.

    But now, after a record-breaking 0-for-54 slump, it's gone.

    Throughout the current deal that began in 2016, Davis is barely above the Mendoza Line, recording a .201 average with a .296 on-base percentage. He's striking out nearly 1.5 times per game, and his power has vanished. In 2018, Davis mustered just 16 homers in 522 plate appearances.

    Davis is frustrated, and the Orioles are stuck.

Rick DiPietro, New York Islanders

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    Kathy Kmonicek/Associated Press

    Contract: $1.5 million per year through 2029

    For a brief stretch in hockey history, players could sign contracts now aptly described as completely ludicrous.

    Rick DiPietro inked the first such agreement in 2006, securing a 15-year, $67.5 million deal with the New York Islanders. Over the next two seasons, he posted a .911 save percentage and made the 2008 All-Star team. Hip injuries affected both those campaigns, though.

    The "i-word" would become all too familiar.

    Multiple knee injuries, several concussions, a groin injury and a broken jaw were among the issues that limited DiPietro to just 50 appearances over the next five seasons.

    The Islanders waived him in 2013, and the buyout still costs them $1.5 million annually until the 16-year payout schedule draws to an end in 2029. 

Jacoby Ellsbury, New York Yankees

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    Mark Brown Photos LLC/Getty Images

    Contract: Seven years, $153 million (through 2021)

    The New York Yankees swiped Jacoby Ellsbury from the rival Boston Red Sox in 2014, but it's turned out better for Boston.

    Injuries have ruined the outfielder's New York tenure. He only made 111 and 112 appearances in 2015 and 2017, respectively, and was kept off the diamond entirely in 2018. As of this writing, Ellsbury has no projected date for a 2019 return, either.

    Even when healthy, he's struggled. Ellsbury has never matched the production of his final season in Boston.

    Per Spotrac, the Yankees will either keep Ellsbury for $21 million or exercise a $5 million buyout option prior to the 2022 season. It's safe to predict which route New York will take.

Ryan Kesler, Anaheim Ducks

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    Jae C. Hong/Associated Press

    Contract: Six years, $41.25 million (through 2022)

    For a decade, Ryan Kesler was a critical piece.

    The center was consistently among the league's top defensive forwards, winning the Frank J. Selke Trophy in 2010-11 and earning five more top-five finishes through the years. He made All-Star teams in 2011 and 2017 and signed a six-year extension along the way.

    From the 2007-08 season through 2016-17, Kesler notched 40-plus points in eight of his nine healthy campaigns. He topped 50 on five occasions and broke the 70-point barrier twice.

    But over the last two years, he's labored to 22 total points with a minus-23 plus/minus in nearly 1,800 minutes.

    Per Spotrac, Kesler owns a no-move clause through 2020 and a limited no-trade clause in 2021.

Joakim Noah, New York Knicks

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    Brock Williams-Smith/Getty Images

    Contract: Four years, $72 million (stretched through 2022)

    Seriously, there must be something in the New York water.

    On Bobby Bonilla Day in 2016, the Knicks finalized a four-year, $72 million deal with free-agent center Joakim Noah. Though he was a two-time All-Star, he'd already begun a sharp decline and had just missed 53 games because of shoulder injuries during the 2015-16 season.

    Nevertheless, he received an enormous contract.

    More injuries and a 20-game suspension for violating the league's anti-drug policy followed, and Noah appeared in just 53 contests for New York. In October 2018, the team waived the bench-ridden center and stretched his remaining contract over a three-year period.

    Until the end of the 2021-22 season, the Knicks will pay him $6.4 million annually not to play for them.

Albert Pujols, Los Angeles Angels

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    John Sleezer/Getty Images

    Contract: 10 years, $240 million (through 2021)

    When the Los Angeles Angels signed Albert Pujols, he'd dominated for 11 years. After the 2011 season, he boasted a .328 career batting average and .420 on-base percentage with 455 home runs.

    By any measurement, he was elite.

    However, Pujols was readying for his age-32 season. Handing out a 10-year contract was begging for trouble near the end, and that's exactly what has happened. Since the beginning of 2015, his on-base percentage barely cracks .300, and the slugger who used to walk more than he struck out is, rather dramatically, doing the opposite.

    According to Barry M. Bloom of Forbes, Pujols said he intends to honor the agreement and play through the 2021 season.

John Wall, Washington Wizards

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    Nick Wass/Associated Press

    Contract: Four years, $169.3 million (through 2023)

    John Wall is immensely talented; he's one of the few NBA players capable of averaging 20 points and 10 assists.

    But his presence has never resulted in anything more than a second-round playoff exit in the perennially weak Eastern Conference. Nine seasons into Wall's career, he's now an injury-plagued veteran approaching the end of a typical athletic prime and the beginning of a massive four-year extension.

    "Nobody will take that contract," a Western Conference executive told Bleacher Report's Ken Berger.

    Wall inked the $169.3 million supermax deal in the summer of 2017, but he's since appeared in just 73 games and is now recovering from heel and Achilles surgeries.

    The Wizards' future is tied directly to Wall, which isn't great news for the franchise.

Andrew Wiggins, Minnesota Timberwolves

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    Jim Mone/Associated Press

    Contract: Five years, $147.1 million (through 2023)

    "[Andrew Wiggins] always leaves me wanting more," one Eastern Conference scout said in January, per Bleacher Report's Eric Pincus. "He doesn't rebound. He doesn't defend. He doesn't get assists. He doesn't shoot well. He'll score ... sometimes, but that's all he does."

    Sounds like your normal $150 million man, right?

    Wiggins is one season into a five-year extension that looked ill-fated when signed in October 2017 and isn't getting any better. In 2018-19, he shot a career-worst 41.2 percent from the field and ranked 45th among small forwards in ESPN's Real Plus-Minus.

    At just 24 years old, his main appeal is "hope for the future." But little evidence provides hope an all-around breakout is coming.

    Follow Bleacher Report writer David Kenyon on Twitter @Kenyon19_BR.