At some point in every Major League Baseball team’s history, a player is signed to a massive contract and fails to deliver the excitement fans were hoping for. Sometimes, these high-risk deals are signed after one incredible season. Other times, they come just as the player is leaving their prime. You know the names: Josh Hamilton, Pablo Sandoval, Chris Davis, etc. But do you remember just how money was shelled out by GMs to sign them? These are the worst MLB contracts of all-time.
Chris Davis, Baltimore Orioles – $161 Million Over Seven Years
Chris Davis found a home in Baltimore in 2013 when he hit 53 home runs and knocked in 138 runs. Two years later he put similar numbers, so the Orioles inked him to a seven-year, $161 million deal. Since then, he’s only hit over .200 twice and hasn’t driven in more than 84 runs.
If Baltimore had taken Davis’ age and strikeout rate into account, they could have seen this decline coming. Instead, the team saw a face of the franchise who led them to the playoffs year after year. In 2017 they missed the playoffs.
Pablo Sandoval, Boston Red Sox – $95 Million Over Five Years
When the Boston Red Sox handed Pablo Sandoval a five-year, $95 million contract in 2015, they thought they were getting a World Series hero. He was only two seasons removed from winning the WS MVP award with the Giants and the contract seemed like a sure bet.
In his first season on the east coast, Sandoval hit .245 with only 10 home runs. Then he missed most of the next season with a shoulder injury. By 2017, Boston had seen enough and released him with two and half years remaining on his contract.
Vernon Wells, Toronto Blue Jays – $126 Million Over Seven Years
From 2002 until 2006, Vernon Wells established himself as one of MLB’s most dangerous hitters. The Blue Jays knew they couldn’t let him go and signed him to a seven-year contract worth $126 million.
The next season Wells immediately regressed. His batting average dropped from .303 to .245 and he hit half as many home runs year-over-year. For the last six years of his deal, he was frustratingly inconsistent and was eventually traded to the Anaheim Angels.
Alex Rodriguez, Texas Rangers – $252 Million Over Ten Years
Sometimes it’s not the contract itself that is so bad, it’s what it does to the surrounding team. Alex Rodriguez played up to the dollar signs when the Rangers signed him to a historic $252 million, ten-year contract in 2001. The team, however, could barely tread water.
Baseball is a team sport, and the Rangers made it financially impossible to put quality teammates around Rodriguez after blowing the bank with his contract. In the deal’s first three seasons, they never won more than 73 games. Before the start of the fourth season, Texas traded their superstar to the New York Yankees.
Josh Hamilton, Anaheim Angels – $125 Million Over Five Years
Josh Hamilton was one of the great comeback stories in MLB when the Angels signed him to a five-year, $125 million contract. The first overall pick by the Tampa Bay Rays in 1999, his career stalled after a struggle with substance abuse.
When Hamilton got sober, he soared. In 2010 with the Texas Rangers won the American League MVP. In 2013, the Angels won the sweepstakes for the free agent, although they didn’t get a good return on their investment and traded him back to the Rangers in 2015.
Mike Hampton, Colorado Rockies – $80 Million Over Six Years
It’s not easy to pitch at Coors Field. The Mile High Stadium makes any contact off the bat dangerous. As a result, the Colorado Rockies have to overpay for pitching, which they willingly did to sign Mike Hampton in 2001.
The former Cy Young winner was miserable in Colorado. After two years as a Rockie, his ERA was a ghastly 5.75. The Rockies admitted defeat and traded him to the Braves. In Atlanta, he was better, although an elbow injury ultimately sidelined his career.
Prince Fielder, Detroit Tigers – $214 Million Over Nine Years
The son of MLB legend Cecil Fielder, Prince Fielder had a fast rise to stardom with the Milwaukee Brewers. When he hit free agency for the first time in 2012, he was a hot commodity. The Detroit Tigers beat out other suitors with a massive contract worth $214 million.
With Detroit, he played in 324 straight games and was mostly worth the money. The problem came in 2013 after the Red Sox eliminated the Tigers from the playoffs and he said, “It’s not really tough for me. It’s over. I’ve got kids I’ve got to take care of. I’ve got things I’ve got to take care of. For me, it’s over, bro.” That same fall he was traded to the Texas Rangers.
Jason Heyward, Chicago Cubs – $184 Million Over Eight Years
The Chicago Cubs signed Jason Heyward to this monster contract in 2016, hoping he was the missing piece. In some ways he was, but not because of his performance. In his first season, he hit .230 and was considered an instant bust.
Then, during a weather delay in game seven of the 2016 World Series, Heyward gave the motivational speech of the century, and the Cubs won their first title in over 100 years! Since then his bat has not backed up his words, and Cubs fans are still waiting for the offense they were promised.
Albert Pujols, Anaheim Angels – $240 Million Over Ten Years
Halfway through his MLB career, most fans thought Albert Pujols would retire a Cardinal. Then he hit free agency in 2012 and joined the Anaheim Angels on a whopping $240 million contract. He was 32-years-old at the time.
While Pujols was decent for the first few years of his contract, the last two seasons have been awful as he has averaged a .243 batting average. Even worse for the team — they owe the slugger $30 million each of the next two years of his contract!
Rusney Castillo, Boston Red Sox – $72.5 Million Over Seven Years
Rusney Castillo was a high priced free agent acquisition by the Boston Red Sox when he defected from Cuba in 2014. The team handed him a seven-year, $72.5 million deal. With so much money going his way, you would think he would be a staple in the everyday lineup.
So far, Castillo has failed to make an impact. He has seen limited MLB action and has spent most of his contract in the minor leagues. In 2016, Boston removed him from the 40 man roster, giving up on the talented international player.
Carl Crawford, Boston Red Sox – $142 Million Over Seven Years
Carl Crawford became a victim of his own body after signing a seven-year, $142 million contract with the Red Sox in 2011. Prior to signing, he was one of the most explosive players in the game.
After signing, he jumped back and forth from the active roster to the injured list. Two seasons into his deal with Boston, Crawford was traded to the Los Angeles Dodgers, where his injury trend continued. In his final season, Crawford only played in 30 games while hitting a paltry .185.
Yasmany Tomas, Arizona Diamondback – $68.5 Million Over Six Years
Another international star who defected from Cuba and earned a big contract in America, Yasmany Tomas is currently in minor league purgatory. When the Diamondbacks signed him for $68.5 million in 2014 they thought they had found their power hitting third baseman of the future.
The plan worked for one season. Tomas bashed 31 home runs in 2016 and drove in 83 runs. Then he lost his 2017 season to shoulder surgery and was sent to the minor leagues in 2018.
Melvin Upton Jr., Atlanta Braves – $72.5 Million Over Five Years
This contract still has us scratching our heads. An elite defender at the time he signed this contract, Melvin Upton Jr. was not a power bat. The Braves took the chance on him anyway, giving him more money then he could ever ask for.
In his first season, Upton’s batting skill imploded and he hit .194. The next year he upped his batting average to .208. Deciding enough was enough, Atlanta shipped him off to San Diego, where he became a starting outfielder for two seasons alongside his brother Justin.
Barry Zito, San Francisco Giants – $126 Million Over Eight Years
Barry Zito was coming off of one of his worst years in Oakland when he became a free agent for the first time. The San Francisco Giants needed to make a splashy move and signed him to a $126 million deal anyway.
In Zito’s first season it was clear the contract was a bad one. In eight years he never recorded an ERA lower than 4.00 and only had a winning record once. In 2012, though, he was a major piece of the Giants’ World Series championship team, making the monetary blow sting a little less.
James Shields, San Diego Padres – $75 Million Over Four Years
The San Diego Padres don’t like to hand out big money contracts, and their deal with James Shields in 2015 might be one of the reasons why. Nicknamed “Big Game” James, Shields’ stuff shrank on the west coast and his ERA ballooned to 5.85 in his second season.
The Padres were quick to act and traded Shields to the White Sox where he continued to struggle. In 2019, San Diego made another splash, signing Manny Machado to a $300 million contract. Let’s hope they got this one right!
Chan Ho Park, Texas Rangers – $65 Million Over Five Years
With the Los Angeles Dodgers, Chan Ho Park was as reliable as they came. He ate innings and kept his ERA low. The Texas Rangers couldn’t miss when the handed him $65 million in 2002.
If that was true, however, Park wouldn’t be on this list. His first year in Texas was a wash as he ate up a less than impressive 149 innings. Season two was even worse as Park finished the year with 29 innings and 7.58 ERA. In his final season, the Rangers were finally able to get Park off the books, sending him to San Diego.
Joe Mauer, Minnesota Twins – $184 Million Over Eight Years
Joe Mauer played with the Minnesota Twins for his entire career. Coming up as a power-hitting catcher, the team locked him into the franchise in 2010 with an eight-year, $184 million contract.
Despite fan loyalty never faltering, injuries caught up with Mauer — specifically, concussions. He was forced to move to first base but was still never the same player. Mauer retired after his 2018 Campaign, a year he only played 127 games and drove in 48 runs.
Ryan Howard, Philadelphia Phillies – $125 Million Over Five Years
Ryan Howard had an incredible career when the Phillies gave him a five-year contract extension in 2010. The $125 million extension officially began in 2012 (it was tacked on the back of his previous contract), and so did his decline.
Before the 2012 season, Howard had driven in more than 100 runs in six straight seasons. He never did again, coming closest in 2014, his last fully healthy in MLB. Howard retired after the 2016 season, a lost campaign where he hit .196 and played 112 games.
Jacoby Ellsbury, New York Yankees – $153 Million Over Seven Years
If any team can afford to hand out bad contracts it’s the New York Yankees. They did exactly that in 2014 when they stole Jacoby Ellsbury from the Boston Red Sox in free agency in 2014.
Ellsbury was efficient enough in his first season, hitting .271 and stealing 39 bases. After that, his body caught up with him and he spent the next several years bouncing back and forth between the Bronx and the injured list.
Homer Bailey, Cincinnati Reds – $105 Million Over Six Years
Homer Bailey was coming off consecutive 200 inning seasons when the Reds inked him to a six-year contract worth $105 million in 2014. Like others on this list, almost as soon as he put pen to paper, his body gave up on him.
Not only has Bailey failed to reach 200 innings since then, but from 2015 until 2018, his ERA never fell below 5.56. In 2019 he signed a contract with the Kansas City Royals, who traded him to the Oakland A’s midseason with a 4.80 ERA.
Jason Bay, New York Mets – $66 Million Over Four Years
Jason Bay had a season that baseball players dream of having when they’re young. His 2009 campaign was incredibly strong with a career-high 36 home runs and 119 RBI. After all that, the New York Mets signed him to a bad four-year deal.
Bay was the recipient of $66 million over four years. During that term, he averaged .229-9-36 and a .688 OPS across 89 games. He ended up finishing the contract and his career with Seattle.
Kevin Brown, Los Angeles Dodgers – $105 Million Over Seven Years
It must’ve been an indescribable feeling for Kevin Brown to become the first player to break the $100 million barrier. We say that because he was approaching age 34 when this happened heading into 1999. The Dodgers must have expected him to be efficient in his late thirties.
Well, the first few years of the contract went well for both parties. Brown finished sixth in the Cy Young voting for two straight years. Then injuries started to plague him and he only started 22 games once over the last five years of the contract.
David Wright, New York Mets – $138 Million Over Eight Years
As fans, it’s hard to see a player with the utmost potential get robbed of a career due to injuries. That’s what happened with David Wright, who could have been a Hall of Famer. After he signed the lucrative contract, he made the last of his seven All-Star appearances.
Then, he started to regress. Wright averaged .269-8-63 with a .698 OPS in 2014. To make things worse, he only played in 77 games in the following four seasons.
Jordan Zimmermann, Detroit Tigers – $110 Million Over Five Years
This is one of those deals where you hope the organization knows something you don’t know. Jordan Zimmermann’s strikeouts started declining and so did his velocity, but that didn’t stop the Tigers from striking early during the 2015-16 offseason.
As his tenure under the contract continues, he’s yet to make 30 starts in a season. His cumulative ERA is 5.24 and his velocity is steady on the decline. Tigers fans should be a little upset at management.
Darren Dreifort, Los Angeles Dodgers – $55 Million Over Five Years
Had Kevin Brown not received that mega-deal years before, then Darren Dreifort’s wild contract wouldn’t have been overshadowed as much. It’s only wild because the Dodgers didn’t get very much out of this right-hander.
In his first season of the contract (2001), he had a 5.13 ERA in 16 starts, then he followed that up by missing all of 2002 to Tommy John surgery. In 2003, he made only ten starts total. You see what we mean?
Miguel Cabrera, Detroit Tigers – $154 Million Over Five Years
Giving players big money even with past injury problems is always a gamble. If a player has a proven track record, then it makes the decision easier, of course, but still, things can always backfire.
The issue with Miguel Cabrera’s contract is how much it’s worth considering he’s been injured in both 2017 and 2018. Many hope that a proper comeback will happen for one of the best hitters of all-time, but he’s in his late 30s.
Eric Hosmer, San Diego Padres – $123 Million Over Seven Years
Eric Hosmer’s career has been on the interesting side. Rooting for him is like being in an on-again, off-again relationship. One year he’s great, but the next he’s a shell of himself. The Padres hope he will be great in 2019 and in the future.
However, when you look at all his “good” years, nothing points toward making him a franchise player, especially in a small market. This was a complete misfire by the management.
Johnny Cueto, San Francisco Giants – $70.4 Million Over Three Years
The San Francisco Giants have multiple questionable contracts on their roster to choose from, but Johnny Cueto’s makes the most sense to reference right now. The Giants had the highest payroll but still lost 89 games in 2018 (98 the year before that).
Cueto had Tommy John surgery heading into the 2019 season which makes this even more interesting. You can only get so much from a guy who isn’t at their full potential. Why such a high contract?
Troy Tulowitzki, Toronto Blue Jays – $37.5 Million Over Two Years
Is it okay to call Troy Tulowitzki a once-great player? After not playing any of the 2018 year, the Blue Jays released him, but the Yankees swiftly picked him up. They also grabbed $555,000 of his 2019 salary.
Unfortunately, the Jays are responsible for the $14 million Tulowitzki will need in 2020, and the $4 million buyout. The scary part is that number could increase by a healthy $6 million based on MVP voting.
Wei-Yin Chen, Miami Marlins – $42 Million Over Two Years
Front offices have been somewhat reluctant to hand out large contracts during free agency the past two winters, and here’s a prime example why. Wei-Yin Chen is a nice player, don’t get us wrong, but he wasn’t a great starter with the Orioles.
Then, the Marlins picked him up for $80 million. In three seasons with the team, he’s gone 13-18, 4.75. In what world is that enough for this kind of money? Let us know when you figure it out.
Dexter Fowler, St. Louis Cardinals – $49.5 Million Over Three Years
Dexter Fowler’s 2018 season was a debacle. We’re not pulling any punches here because he hit .180/.278/.298 for minus-1.4 WAR. With numbers like that, his starting spot was no longer guaranteed heading into the 2019 season. Especially with Tyler O’Neill and Jose Martinez playing right field.
Fowler isn’t washed up just yet, but he’s getting up there in age. The thirties are scary years when it comes to outfielders so it remains to be seen how this will end up.
Kyle Seager, Seattle Mariners – $57.5 Million Over Three Years
The Mariners are a team filled with “wish we didn’t have them” contracts such as Robinson Cano’s or Jay Bruces. However, Kyle Seager’s contract is a bit of a disaster and we’ll tell you why.
For one, the $100 million extension they gave him was questionable because the guy isn’t that athletic (can he even run?). Also, he’s a one-dimensional swinger and gets hurt by the shift. He finished 2018 with a fractured toe and had okay averages, so maybe he’ll pick up the slack in the near future.
Zack Greinke, Arizona Diamondbacks – $104.5 Million Over Three Years
All signs point towards Zack Greinke’s contract being a good one. He didn’t have a very promising first season with the Backs, but the two seasons after were solid. He topped 200 innings with ERAs of 3.20 and 3.21.
Also, his 10.3 WAR across those two seasons ranked him eighth among starting pitchers. See what we mean? Everything looks to add up in his favor, but if his massive contract was a good deal, Arizona would have traded him heading into the 2019 season.
Daisuke Matsuzaka, Boston Red Sox – $52 Million Over Six Years
In 2007, the Boston Red Sox took a chance on a Japanese phenom Daisuke Matsuzaka when they signed him to a six-year, $52 million contract. The gamble looked like it was paying off in his first year in Boston (fourth in Rookie of the Year voting).
The next year was pretty good too as he finished fourth in Cy Young voting. Sadly, it would be the final four years of the contract that stunk. He was riddled with injuries and his ERA never shot above 5.50.
Carlos Beltran, New York Yankees – $45 Million Over Three Years
Carlos Beltran isn’t someone who has a reputation for being clutch. When he played for the Mets, the one pitch he failed to swing at summed up his career. After bouncing around, he returned to New York as the Yankees hoped he could help bring them to the playoffs.
Unfortunately, his play in the pinstripes wasn’t as stellar as they hoped. In the first two seasons with the team, he missed more than 80 games thanks to injury.
Matt Kemp, Los Angeles Dodgers – $160 Million Over Eight Years
Players always find a way to play outstandingly when it’s a contract year. Ask Matt Kemp, who finessed the Dodgers out of millions after his sensational 2011 year. Los Angeles repaid his efforts with a franchise-record contract extension.
Magically, after signing for all that money, Kemp’s play drastically fell the following season. The Dodgers eventually had enough and traded him to the Padres, where his averages would plummet even further. Maybe all the money got to his head.
A.J. Burnett, New York Yankees – $82.5 Million
Pitching is one thing you can never have too much of. Thats a philosophy the Yankees followed when they signed A.J. Burnett to that massive five-year deal in 2009. The Yankees might have ended that season as the world champs, but things would go bad soon.
The following two years weren’t that spectacular. Burnett only won 21 games combined and his ERA rose to 5.20. Finally, in 2011, the Yankees traded him to the Pittsburgh Pirates after agreeing to pay over half of the remaining salary.
Jayson Werth, Washington Nationals – $126 Million Over Seven Years
The Nationals were at the bottom of the barrel for many years. Then, in 2010, they made a splash by bringing Jayson Werth to the team on a crazy seven-year deal. He was a new face, but he wasn’t the solution.
Following the acquisition, Werth was a below average player that saw superstar money. Over five years in Washington, the slugger only hit 78 home runs and couldn’t finish multiple seasons because of injury woes.
Carlos Lee, Houston Astros – $100 Million Over Six Years
The signing of Carlos Lee in 2007 to a six-year deal was major news. During his first three years of that huge contract, it looked like the Astros were going to get what they paid for.
After the 2009 season, Lee’s numbers began to fall. Someone who used to be a .300 hitter became a .246 hitter. His home run numbers dropped as well, hitting around 20 a season. The Astros never made the playoffs in his time there.
Nick Swisher, Cleveland Indians – $56 Million Over Four Years
If you know Nick Swisher, then you know he’s always been a personable guy. After leaving the Yankees, he charmed his way onto the Cleveland Indians roster and got a great four-year deal too.
In his second season there, his playing skills dropped drastically. He lost some power, only played in 97 games due to injury, and he batted .208. In 2014, he had to undergo arthroscopic knee surgery on both knees, which caused him to miss the remainder of the season. He came back the next year and only played 30 games before getting traded.