A contract bust in baseball is fundamentally different than those in other major sports. On the one hand, there’s no salary cap, so a bad contract or two won’t necessarily cripple a team’s ability to compete in the coming years. On the other, all of these contracts are fully guaranteed, meaning that unlike NBA or NFL players, MLB stars are getting paid out for the rest of their deal whether they’re even remotely capable of playing at a major-league level or not. So, if the New York Giants realizes half a year into a seven-year deal that their big free agent has lost a step, they can jettison him and his contract. But, if the San Francisco Giants find themselves in a similar situation, they just have to take their medicine for as long as the deal lasts.
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To determine which MLB contract really represents the biggest bust, GOBankingRates looked at some of those deals noted as being among the worst in league history. Then, it determined how well the player performed using his average OPS and WAR during the deal along with the player’s total home runs and RBI. The study then took what the deal ended up representing in terms of dollars paid per game played and per hit struck and the percentage of the games from the player’s contract that he actually played in. Each category was then scored and the contracts were ranked by that combined score, with No. 1 being the worst bust.
Last updated: July 7, 2021
25. Jacoby Ellsbury
Ellsbury was known as one of the league’s best leadoff men and center fielders for much of his career in Boston, finishing second in MVP voting in 2011, clearing 50 steals in a season on three separate occasions and showing sparkling skills in the field. But, he committed the ultimate betrayal in the world of baseball — signing a deal with the Evil Empire in the Bronx. The seven-year, $153 million contract broke the hearts of Red Sox nation.
However, in what Boston fans must have found to be an incredibly enjoyable turn of fate, Ellsbury’s on-base percentage took a nose-dive, and his defensive skills also declined as he aged. He would ultimately make over $275,000 a hit as he sustained just a 0.716 OPS with the Yankees.
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24. Kenji Johjima
The vast majority of Kenji Johjima’s storied career occurred in Japan, so it’s important to remember that his stint in America really shouldn’t be what he’s judged by. However, for Seattle fans, the end to his career in America was one that wound up costing their team. Johjima had hit 32 home runs in his first two seasons with the club, with an OPS over 0.750 both years — numbers that will keep a catcher working in the MLB as long as their defense is up to snuff. As such, Seattle extended him with a three-year, $24 million deal after the 2007 season.
But, Johjima was already 32 by the time he started playing on the contract, and catchers age faster than virtually any other player on the diamond. He would manage just a 0.689 OPS over the next two seasons before returning to finish his career in Japan.
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23. Chris Davis
Chris Davis has had a real roller coaster of a career. He was a highly touted hitting prospect in the Rangers organization who spent years looking like he was on the verge of taking the next step only to come up just a bit short. After a trade to Baltimore, though, he almost immediately broke out, finishing third in the MVP voting in 2013. And, while 2015 was a down year for him, he still signed a massive seven-year, $161 million contract.
Though his first year on the deal was excellent, Davis managed an OPS of just 0.666 with the Orioles after signing, earning over $275,000 a hit in the process.
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22. Ryan Howard
Subway spokesman Ryan Howard was always a swing-and-miss hitter, leading the league in strikeouts just as many times as he did home runs — twice. In his best years, the danger of his home run stroke translated to a high on-base percentage as teams tended to pitch around him. At some point, though, after he signed a five-year, $125 million extension in 2010 (that would kick in in 2012), Howard stopped making hard contact. As his power declined, so did his walk rate and soon he was striking out a lot with no home runs to show for it. After 2011, Howard would never manage more than 25 homes in a season and he would ultimately produce an OPS of just 0.724 on that contract.
21. Mo Vaughn
Hefty first baseman Mo Vaughn is another player who rode a crushing power stroke to an MLB career. That reputation earned him a well-deserved six-year, $80 million contract with the Angels in 1999 — a contract that he was well on his way to living up to through the first two seasons as he hit 30-plus home runs with an OPS over 0.850. But, he was 32 during that second season, and his years of service were starting to catch up to him.
Vaughn ended up missing all of his third season with the club to injury and was never the same afterward. He finished his career with the Mets, hitting 26 homes runs with an OPS over 0.800 in 2002 — a strong showing, but well short of what he needed to justify his salary.
20. Juan Gonzalez
The most disastrous transaction involving Juan Gonzalez is most likely the trade that sent him to the Tigers — Detroit ended up selling the farm for a single season of subpar performance. If you just want focus on free agent contracts, though, it would be the one he signed a couple years after that trade that stands out.
Gonzalez had made his name with Texas, where he had started his career at 19 and played for 11 seasons. He signed a two-year, $24 million deal with the Rangers to return to Arlington for the 2002 season, but his second stint was not as glorious. He would manage just 152 games over those two years, ultimately making nearly $200,000 per hit.
19. Melvin Upton
The Upton brothers were both elite outfield prospects, but while Justin managed to turn the corner on his career as a star outfielder, Melvin never quite managed to make enough contact. He did have the look of a potential 40-40 guy early in his career, stealing at least 35 bases in four different seasons during his first MLB stint in Tampa as well as three seasons of 20-plus home runs. That sort of power-speed combo is incredibly tempting. So, when he hit free agency in 2013, there were clubs ready to take a chance on a guy who always seemed to struggle with getting on base often enough.
The team that ended up getting Upton was the Braves, with a five-year, $72.5 million contract. Unfortunately for Atlanta, his abilities got worse, not better, and he would end up with an OPS of 0.651 with just 47 RBI.
18. Julio Lugo
Julio Lugo had already made four different major league stops in his career prior to signing with the Red Sox before the 2007 season. A veteran talent who had always shown a bit of pop in his bat for a middle infielder, Lugo got the BoSox to sign him to a four-year, $36 million deal.
While the team won the World Series in that first year, Lugo’s performance went south in a hurry in Boston. His OPS with the club wound up being 0.666 and he hit just 12 home runs over the course of the deal — not what you’re expecting when you shell out $9 million a season on a player.
17. Vince Coleman
There have been just 22 100-steal seasons in MLB history, so the fact that Vince Coleman has three of them is pretty impressive — all the more when you consider they were consecutive. When the Mets signed him to a four-year, $12 million deal in 1991, he had led the league in steals in all six of his major league seasons — swiping 77 the year before.
Unfortunately for the Mets, Coleman finished his career without ever winning another steals title — not to mention never clearing a total of 50 again. His OPS fell to 0.676 and the Mets surely regretted paying him $4 million a season.
16. Jason Bay
Jason Bay pretty consistently hit for an OPS over 0.900 for most of his career. So, if you’re wondering why his career OPS is 0.841, well, you need look no further than the 0.670 OPS he hit for over the course of the four-year, $66 million contract he signed with the Mets in 2010.
Bay was entering his age-31 season when the Mets signed him, which is right about the time that players start to lose a bit of bat speed and see their batting stats erode. Bay saw a drop in OPS of over 170 points in his first season with the Mets, and he hit no less than 30 fewer homers. It didn’t get much better from there, as the three-time all star had clearly just passed his prime by the time he arrived in Queens.
15. Bobby Bonilla
Ah, Bobby Bonilla, the grand poobah of all bad contracts. For those not in the know, this one wasn’t exactly a disaster when the Mets initially signed it. The real tale is not Bonilla’s failure to hit well enough to keep a roster spot, it’s that the Mets ownership decided to offer him an absurd deal where they would pay him about $1.2 million every season from 2011 to 2035 instead of the remaining $5.9 million left on his contract. The deal was offered because the team’s ingenious money manager Bernie Madoff was earning them such an enormous return.
Bonilla played in just over 15% of the games he signed on for, and he’ll wind up making nearly $700,000 for every hit he delivered the Mets.
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14. Jeffrey Hammonds
If there’s one thing you don’t do, it’s offer a big contract to a hitter who just had a breakout season during his first year playing in Colorado. The thin air of Coors Field has always boosted offensive numbers there, and thinking that a guy’s sudden power stroke is for real can end up costing you. This happened when the Milwaukee Brewers offered Jeffrey Hammonds a three-year, $21 million deal in 2001, fresh off his hitting 0.335 for Colorado with 20 homers and 106 RBI. Over the next three years — as his home games were closer to sea level — Hammonds managed just 19 home runs and 75 RBI.
13. Scott Spiezio
After Scott Spiezio had enjoyed a productive stay in both Oakland and Anaheim, perhaps the Seattle Mariners were thinking every AL West team was going to get a go when they inked him to a three-year, $9 million deal in 2004. Spiezio, though, was heinously bad in the Emerald City — hitting just .215 in his first year and then 0.064 in his second. By the third, he was in St. Louis and was productive again, but his stay with the Mariners was so bad even $3 million a season was woefully overpaying him.
12. Milton Bradley
Not a typo, this major league outfielder had a real monopoly on board game names during his time in the MLB. When he signed with the Cubs — by way of a three-year, $30 million deal in 2009 — he had already been an important player on six different teams. However, it was that sixth one — the Texas Rangers — where Bradley suddenly produced a monster 0.999 OPS during the 2008 season, hitting 0.321 with 22 home runs and 77 RBI. This, of course, got the attention of the Cubs, who hoped to replicate those stats.
Unfortunately for Chicago, Bradley was due to come back to earth in a serious way. His OPS on that deal would be under 0.700 and he would manage just 22 home runs and 82 RBI.
11. Gary Matthews Jr.
If you haven’t seen Gary Matthews Jr. making THE catch, you should hit YouTube right now to check it out. That wall-climbing miracle was the sort of play the Angels were thinking of when they offered the then-Ranger a five-year, $65 million deal in 2007. But, Matthews was going to be 32 in his first season with the Angels, and father time had a little something to say about signing a guy to a contract that would have him still playing at 37.
Matthews would produce 18 home runs and steals in year one, but that dropped to eight of each in his second year and four of each by year three. All told, his OPS on the deal was 0.655 and he pulled down nearly a quarter-million dollars per hit.
10. Carl Crawford
Speed is one attribute that tends not to age well, with even the best speedsters rarely managing to continue swiping bags into their 30s. Crawford would produce more than 45 steals in eight of his first 10 seasons — all with Tampa Bay — and was easily the one guy opposing catchers feared the most in the league. So, when he came up for free agency in 2011, Boston went big to land him — offering a seven-year, $142 million deal.
The thing is, Crawford would never clear 45 steals in a season again — in fact, he would only top 20 once. The good news for the Red Sox is that they managed to dump the contract on the Dodgers after just two years, but Crawford would end up earning over $350,000 a hit for the deal.
9. Yasmany Tomás
It can be very difficult to gauge how foreign players will fare against MLB competition. Top performance in Cuban, Japanese or Korean leagues can often be a clear sign a player’s going to be a big star. Just as often, however, guys who scouts assume will be great fall flat on their face in their new surroundings.
Yasmany Tomás arrived from Cuba and signed a six-year, $68.5 million deal with the Diamondbacks. Unfortunately, his career 0.306 OBP makes it hard to justify starting him every day, and his WAR stats indicate that he’s costing his team more games than he’s winning them.
8. Josh Hamilton
Josh Hamilton’s incredible story of redemption might not be as easy to enjoy for Angels fans. That’s because after he was a top prospect who lost it all to drugs and alcohol only to get clean and come back to win the AL MVP in 2010, he then signed a five-year, $125 million deal with Anaheim — just in time for him to stop hitting. This is made all the more galling by the fact that his career with division rival Texas meant he did a disproportionate amount of damage to Angels pitching.
Hamilton’s still an inspiring story of fighting for a second act and getting it, but it does have the coda of him absolutely fleecing the Angels with his last contract, earning almost $475,000 a hit.
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7. David Wright
You’re not likely to find a ton of Mets fans who don’t have at least some love in their hearts for David Wright, in spite of this stinker of a contract. The eight-year, $138 million deal he signed in 2013 could be seen as him finally getting the reward he really deserved for his years of loyal service. His Mets career would see him play over 1,500 games for the franchise.
Unfortunately for Wright and Mets fans alike, he suffered through injuries that seriously hampered his ability to make good on the deal. He would ultimately play in less than a third of the games he signed on for, with his last MLB appearance coming in 2018.
6. Pablo Sandoval
Before you start to get too critical of Pablo Sandoval, keep in mind that a lot of people start putting on weight in their late 20s. And a lot of people might also ease up on their career a bit after they’ve locked in $95 million in salary over the next five years. So, the fact that he really let his conditioning slide in the aftermath of the deal he signed with the Red Sox in 2015 just shows he’s, well, human.
That said, he did end up fleecing the Red Sox something fierce. Kung Fu Panda’s 0.596 OPS on the deal speaks to just how far his skills at the plate slid the moment he arrived in Boston, and he would appear in just about half the games represented by that deal. In the end, Sandoval would make over $340,000 per hit.
5. Ken Caminiti
One thing the steroid era really warped was fans’ perceptions about just how productive a player would be late into his career. Take, for instance, Ken Caminiti winning the MVP at age 33 in 1996 — a season he’s since admitted was fueled by PEDs. The fact that the Rangers were ready to sign him to a two-year, $9.5 million deal in 2001 when Caminiti was going to be 38 by the first game of the season shows the degree to which teams had forgotten the limitations of the human body.
Caminiti would not finish the season with the Rangers and he wasn’t there for year two — producing just 41 RBI and 15 homers in his brief playing time.
4. Yoenis Cespedes
Cespedes produced relatively strong stats on the four-year, $110 million deal he signed with the Mets in 2017. His 0.857 OPS is the second highest in this study, showing that it wasn’t an inability to hit that made his contract a bust. In actuality, injuries have severely limited his ability to play.
Cespedes has appeared in just under a quarter of his contracted games thus far, meaning the Mets have paid more than $700,000 per hit on his deal.
3. Andruw Jones
Five-time all star Andruw Jones was a dazzling player throughout his time in Atlanta, notching the best of his 17 years in baseball and producing most of his 434 career home runs. However, by the time the Dodgers signed him in 2008, Jones was largely a spent force, not the power that finished second in MVP voting in 2005.
Over the course of the two-year, $36.2 million deal, he would produce -0.7 WAR — the worst performance of anyone in this study. Jones would ultimately make over $450,000 for each hit during those two years.
2. Rusney Castillo
Perhaps the all-time biggest mistake when it comes to international talent, Rusney Castillo came out of Cuba with most of the league salivating at the thought of landing him for their squad. The Red Sox were willing to overlook his total lack of MLB experience because of his great tools and success in Cuba, signing him to a seven-year, $72.5 million contract in 2014.
Sadly, Castillo was not major-league ready, and that same contract became an albatross that would prevent him from playing in the big leagues after his demotion in 2016. He is still earning a ton, but he’s languishing at AAA Pawtucket — not what you want from a contract worth over $10 million a year. To this point, Castillo has earned over $675,000 per game and $800,000 per hit.
1. Danny Tartabull
So, by some standards, no one-year deal can really be that big of a bust, especially when it’s only for $2.3 million. However, judged by the metrics used in this study, Danny Tartabull’s last “season” in baseball is actually the single biggest strikeout that any MLB GM has ever produced.
Sure, expectations from the Phillies couldn’t have been too high, given they only signed him for that one year. But, even they must have been more than a little peeved about getting 11 at-bats over three games from the outfielder. Had he gotten a hit, he would have been paid an inflation-adjusted $3.67 million for it. He didn’t, though, so he just ended up getting that amount for nothing.
Pictured: Danny Tartabull in 1993 when he played for the New York Yankees
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Methodology: In order to find the biggest MLB contract busts of all time, GOBankingRates analyzed notably disappointing non-rookie contracts. GOBankingRates referenced BleacherReport’s “The 20 Biggest Busts in the History of MLB Free Agency” and YardBarker’s “The Worst Contracts in MLB history”, as well as Spotrac data for some of the current and all-time most expensive contracts in the MLB. With 48 players/contracts selected and adjusted for inflation to 2020 dollars, GOBankingRates scored them across the following factors: (1) dollars per game calculated by taking the inflation-adjusted value of the contract and dividing it by total games played for the duration of the contract; (2) total percent of games played calculated by dividing games played against the maximum possible games during the contract; (3)average OPS throughout contract; (4) dollars per hit calculated by finding each players total hits during contract and dividing by contract value: (5) total RBIs during contract; (6) total HRs during contract; and (7) average WAR during length of contract. All statistics were sourced from Baseball Reference. All factors were then scored and combined with the highest score determining the biggest MLB contract bust of all time. During calculations factors (2) and (7) were weighted double and factors (3) and (6) were weighted 1.5 and 0.5 times respectively. All data was collected on and up to date as of July 13, 2020.
This article originally appeared on GOBankingRates.com: Biggest Contract Busts in MLB History