The 10 Worst Contracts in Major League Baseball

Every offseason, some team overpays, or spends big money to retain or bring in a prized free agent. But more often than not, those massive contracts don’t pan out the way teams pray they do, especially towards the backend of them. Here are the 10 worst contracts in Major League Baseball.

10) Homer Bailey — fifth year of a six-year, $105 million deal

Homer Bailey was quietly one of the more underrated righties in the game just five years ago. But back in 2014, the Cincinnati Reds opted to give Bailey a six-year deal which they now immensely regret. He’s started just 61 games since signing the deal and recorded ERAs over five from 2015-17. The Reds thought Bailey would prosper and continue to be a viable top-of-the-rotation starter, but he’s now a salary they wouldn’t mind to begone with.

9) Felix Hernandez — sixth year of a seven-year, $175 million deal

Seattle Mariners righty, Felix Hernandez, was, at one point, the most intimidating right-hander in the game. Unfortunately for he and the Mariners, he’s now one of the most overpaid players in the game. He’s having the worst season of his career (Hernandez currently owns a career-worst 5.10 ERA and 1.35 WHIP), has been on the disabled list in years past, and is reeling in, on average, $25 million a year. He’s a classic example of how giving players massive contracts in their prime can backfire at the backend of the deal.

8) Jordan Zimmermann — third year of a five-year, $110 million deal

Jordan Zimmermann was a top-10 starter after the 2014 season and was still a premier righty when he hit the open market after the 2015 season, but he’s now a shell of his old self. He puts runners on base with ease and has struggled to remain heathy and be the top-of-the-rotation force that the Detroit Tigers signed him to be. Last season, he even recorded career-worsts in ERA (6.08), WHIP (1.55), and home runs (29). Due $74 million through 2020, Zimmermann has one of the worst contracts in the game and will be hard to move via trade.

MLB teams ink a bounty of laughable, regrettable contracts every year, but these 10 contracts stand out as the worst in baseball.Click To Tweet

7) Yoenis Cespedes — second year of a four-year, $110 million deal

Yoenis Cespedes, when healthy, is one of the best power-hitting and all-around outfielders in baseball, but that’s where the problem lies with the 32-year-old. He’s the most important player on the Mets roster. Without him, their lineup crumbles. Over the last two years, Cepsedes has played just 118 games, and there are even times when it appears he’s playing through injury — which is admirable. But for the Mets, their best player struggles to stay on the field and they pay him, on average, $27.5 million per year.

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6) Jacoby Ellsbury — fifth year of a seven-year, $153 million deal

The New York Yankees went on a spending spree after the 2013 season, and outfielder Jacoby Ellsbury was a big part of it. Four years later, it’s one of general manager Brian Cashman’s biggest mistakes. In his four years with the Yankees, Ellsbury has never hit at, or above .275, has struggled to stay healthy, and has gradually fallen out of the Yankees outfield rotation. This season, the 34-year-old hasn’t played a single game due to injury, and if he ever returns to the field this season, Ellsbury will likely get limited playing time. The signing has been a complete disaster for the Yankees, and it will only get worse going forward if and when he doesn’t start upon returning.

5) Jason Heyward — third year of an eight-year, $184 million deal

Jason Heyward is one of the best defensive outfielders of this decade, but his inability to be a threat at the plate makes him one of the games most overpaid players. He’s never finished a season hitting at or above .260 with the Chicago Cubs, was, at one point, swapped in and out of manager Joe Madden’s order in the postseason, and simply striked while the iron was hot in terms of his worth in dollars. The Cubs have the third highest payroll in the game. Imagine if they opted to spend elsewhere, or not use Heyward’s money? They could’ve been set up to make a run at two premier free agents this offseason.

4) David Price — third year of a seven-year, $217 million deal

Two offseasons ago, the Boston Red Sox felt compelled to go out and add an ace; they opted to show lefty David Price the money — which has panned out to be a disaster for Boston. Ranging from enduring an elbow scare last season, to disappointing in the 2016 postseason (where he surrendered five runs in 3.1 innings pitched), to simply pitching with inconsistency, Price has not been as advertised for Boston. Sure, Price has been respectable when he’s taken the hill, but the ace of old is no more. Red Sox president Dave Dombrowski is known for being aggressive on the trade and free agent market, but the signing of Price has not been some of his most finest work.

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3) David Wright — sixth year of an eight-year, $138 million deal

David Wright is New York Mets’ royalty, but his inability to play in the big leagues is killing their payroll. He hasn’t played in a Major League game since 2016 and played a combined 75 games from 2015-16. Wright continues to try to return to form and make it back to the big leagues, and it’s not out of the realm of possibility that he’ll do so. But given his financial situation and injury prone track record, the 35-year-old is and has been one of the game’s worst contracts.

2) Chris Davis — third year of a seven-year, $161 million deal

Three years ago, Baltimore Orioles first baseman Chris Davis was one of the most feared left-handed hitters in the game. He demolished baseballs and even hit a combined 164 home runs from 2013-16. But in the past two years, this one in particular, he’s fallen off a cliff and is one of the worst hitters in the game. Hitting just .152 and recording 98 strikeouts in 65 games this season, he’s basically been a veteran version of Joey Gallo. Under contract through 2022 and having money deferred through 2037, the Orioles will constantly be reminded of the $161 million mistake they made in re-signing Davis.

1) Miguel Cabrera — third year of an eight-year, $248 million deal

Detroit Tigers corner infielder, Miguel Cabrera, is one of the greatest hitters in MLB history; he’s a career .316 hitter who hits for contact and has booming power. But based on his 2017 play (Cabrera hit a career-worst .249 and drove in just 60 runs in 2017), the fact that he’s 35 and recently suffered a ruptured biceps tendon — ending his season — Cabrera’s contract is the worst in baseball. He’s due $30 million-plus annually through 2023, and he could potentially be on the Tigers’ payroll through 2025 given that he has a mutual option for $30 million per season in 2024 and 2025. That means in seven years, the Tigers could be paying a 42-year-old, out his prime, $30 million a year; it’s arguably the worst contract in baseball history.

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