The Worst Major League Baseball Contracts Of All Time

Some Major Leauge Baseball players get very lucky when it comes to signing onto big contracts. These athletes can make millions of dollars per year, but these deals don't come without risk. Sometimes deals are signed after just one season, and sometimes they're signed just as a player is nearing the end of his career.

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? Keep reading to find out.

Troy Tulowitzki Signed To The Toronto Blue Jays For $37.5 Million Over Two Years

Troy Tulowitzki #2 of the Toronto Blue Jays throws out the baserunner in the third inning during MLB game action against the Baltimore Orioles at Rogers Centre on June 27, 2017 in Toronto, Canada-802229574
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The Toronto Blue Jays thought they had struck gold when they signed Troy Tulowitzki on to a 2 year contract for $37.5 million. Unfortunately, Tulowitzki failed to deliver the goods. He didn't play at all in 2018 and the Jays ended up releasing him from the team. The Yankees picked him up as well as $555,000 of his 2019 salary.

The Jays are still responsible for the $14 million Tulowitzki will need in 2020, and the $4 million buyout.

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Ryan Howard Signed To The Philadelphia Phillies For $125 Million Over Five Years

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In 2010, The Philadelphia Phillies decided to give one of their star players, Ryan Howard, a five-year contract for $125 million. The extension was supposed to officially begin in 2012. Unfortunately, in 2012, Howard wasn't playing as well as he had in the past.

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He ended up retiring after the 2016 season. That year he hit .196 and played 112 games. He had already passed his prime when he signed that five-year contract, but the Phillies didn't know that.

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Jacoby Ellsbury Signed To The New York Yankees For $153 Million Over Seven Years

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The New York Yankees are one of the most profitable Major League Baseball teams of all time. If anybody can afford to take a hit on a bad contract, it's the Yankees. They actually did end up taking a hit in 2014 when they signed Jacoby Ellsbury who was formerly on the Boston Red Sox team.

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Ellsbury did well in his first season, hitting .271 and stealing 39 bases. After that, he ended up spending half of his time on the metaphorical bench due to a series of injuries.

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Joe Mauer Was Signed To The Minnesota Twins For $184 Million Over Eight Years

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Baseball player Joe Mauer has never played with a major league team other than the Minnesota Twins. That's what loyalty really looks like. Did he actually have a choice, though? In 2010, the Twins locked this power-hitting catcher into the franchise for eight years with a $184 million contract.

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Mauer always had a loyal fanbase, but he got injured several times during his career with the Twins. He was eventually forced to move to first base. He retired in 2018 after only playing in 127 games that year.

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Homer Bailey Signed To The Cincinnati Reds For $105 Million Over Six Years

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Homer Bailey was a sure thing in 2014 when the Cincinnati Reds signed him onto a six-year contract for $105 million. They thought they were getting a good deal because he just came off consecutive 200 inning seasons. As soon as Bailey signed the contract, his body gave up on him.

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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.

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Chris Davis Signed To The Baltimore Orioles For $161 Million Over Seven Years

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Chris Davis started playing for the Baltimore Orioles in 2013. That year, he hit 53 home runs and knocked in 138 runs. Davis kept that momentum up for the next two years, so the Orioles decided to sign him on to a seven-year deal for $161 million. Since then, he's only hit over .200 twice and hasn't driven in more than 84 runs.

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Baltimore should have seen this coming. Davis' age and strikeout rate weren't looking good, even when he was making those runs.

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Vernon Wells Signed To The Toronto Blue Jays For $126 Million Over Seven Years

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Vernon Wells became one of the MLB's most beloved hitters in 2002. He kept up that streak until 2006, and by then, the Blue Jays knew that they didn't want to let him go. They signed him to a seven-year contract worth $126 million.

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All of that security must have gone to Wells' head because the next year, his batting average dropped from .303 to .245 and he hit half as many home runs year-over-year.

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Alex Rodriguez Signed To The Texas Rangers For $252 Million Over Ten Years

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Alex Rodriguez is an excellent ballplayer and was well worth the big bucks. In 2001, this superstar signed onto a ten-year contract worth ahistoric $252 million with the Texas Rangers. Alex did well on the Rangers, but his ginormous price tag meant that the franchise couldn't afford to get him enough decent teammates.

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In the deal's first three seasons, the Rangers never won more than 73 games. Before the start of the fourth season, Texas traded Rodriguez to the New York Yankees.

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Josh Hamilton Signed To The Anaheim Angels For $125 Million Over Five Years

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The Anaheim Angels signed Josh Hamilton into a five-year, $125 million contract. Hamilton was the first overall pick by the Tampa Bay Rays in 1999, but his career stalled after a struggle with substance abuse.

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Hamilton was able to get clean and make a comeback, though. In 2010 he helped the Texas Rangers win the American League MVP. This guy proves that a bad deal doesn't have to stay a bad deal forever. Players can always turn themselves around.

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Mike Hampton Signed To The Colorado Rockies For $80 Million Over Six Years

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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.

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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.

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Prince Fielder Signed To The Detroit Tigers For $214 Million Over Nine Years

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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.

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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.

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Jason Heyward Signed To The Chicago Cubs For $184 Million Over Eight Years

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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.

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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.

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Pablo Sandoval Signed To The Boston Red Sox For $95 Million Over Five Years

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The Boston Red Sox gave Pablo Sandoval a five-year, $95 million contract in 2015. At the time, the team thought the were acquiring a World Series champion. Sandoval was only two seasons removed from winning the WS MVP award with the Giants. This contract seemed like a sure thing.

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In his first season with Boston, Sandoval hit .245 with only 10 home runs. Then a shoulder injury took him out of the next season. By 2017, Boston had seen enough and released him with two and half years remaining on his contract.

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Albert Pujols Signed To The Anaheim Angels For $240 Million Over Ten Years

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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.

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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!

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Rusney Castillo Signed To The Boston Red Sox For $72.5 Million Over Seven Years

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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.

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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.

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Carl Crawford Signed To The Boston Red Sox For $142 Million Over Seven Years

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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.

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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.

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Yasmany Tomas Signed To The Arizona Diamondback For $68.5 Million Over Six Years

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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.

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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.

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Melvin Upton Jr. Signed To The Atlanta Braves For $72.5 Million Over Five Years

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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.

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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.

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Barry Zito Signed To The San Francisco Giants For $126 Million Over Eight Years

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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.

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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.

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James Shields Signed To The San Diego Padres For $75 Million Over Four Years

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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.

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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!

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Chan Ho Park Signed To The Texas Rangers For $65 Million Over Five Years

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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.

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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.

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Jason Bay Signed To The New York Mets For $66 Million Over Four Years

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General Manager Omar Minaya watches Jason Bay and put on a New York Mets hat as Mets COO Jeff Wilpon looks on during a press conference to announce Bay's signing to the New York Mets on January 5, 2010 at Citi Field in the Flushing neighborhood of the Queens borough of New York City-95590271
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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.

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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.

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Kevin Brown Signed To The Los Angeles Dodgers For $105 Million Over Seven Years

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Major league baseball pitcher Kevin Brown listens to questions during a press conference 15 December where he met with the media following the signing of his 105 million dollar, seven-year contract with the Los Angeles Dodgers. The four-time, All-Star Brown became the highest paid baseball player in history.-51623146
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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.

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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.

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David Wright Signed To The New York Mets For $138 Million Over Eight Years

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Third baseman David Wright #5 of the New York Mets poses during photo day at Tradition Field on February 27, 2010 in Port St. Lucie, Florida-97138925
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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.

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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.

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Jordan Zimmermann Signed To The Detroit Tigers For $110 Million Over Five Years

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Jordan Zimmermann #27 of the Detroit Tigers speaks to members of the media prior to a MLB baseball game between Tigers and Washington Nationals at Nationals Park on May 9, 2016 in Washington, DC-531503230
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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.

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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.

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Darren Dreifort Signed To The Los Angeles Dodgers For $55 Million Over Five Years

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Pitcher Darren Dreifort #37 of the Los Angeles Dodgers in action during an interleague game against the Texas Rangers at the Ball Park in Arlington, Texas. The Dodgers won the game, 4-1-321767
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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.

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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?

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Miguel Cabrera Signed To The Detroit Tigers For $154 Million Over Five Years

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Miguel Cabrera #24 of the Detroit Tigers argues with the umpires in the ninth inning against the Pittsburgh Pirates while wearing the #42 to commemorate Jackie Robinson Day during the game at PNC Park on April 15, 2015 in Pittsburgh, Pennsylvania-469859612
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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.

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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.

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Eric Hosmer Signed To The San Diego Padres For $123 Million Over Seven Years

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Eric Hosmer #30 of the San Diego Padres poses on photo day during MLB Spring Training at Peoria Sports Complex on February 21, 2018 in Peoria, Arizona-922326122
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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.

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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.

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Johnny Cueto Signed To The San Francisco Giants For $70.4 Million Over Three Years

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Johnny Cueto #47 of the San Francisco Giants delivers a first inning pitch against the Arizona Diamondbacks at Chase Field on May 12, 2016 in Phoenix, Arizona-531108214
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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).

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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?

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Wei-Yin Chen Signed To The Miami Marlins For $42 Million Over Two Years

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Wei-Yin Chen #54 of the Miami Marlins looks on from the dugout prior to a game against the St. Louis Cardinals at Busch Stadium on June 7, 2018 in St Louis, Missouri-969335412
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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.

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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.

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Dexter Fowler Signed To The St. Louis Cardinals For $49.5 Million Over Three Years

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Dexter Fowler #25 of the St. Louis Cardinals celebrates in the dugout after hitting a grand slam home run in the 6th inning against the Chicago White Sox at Guaranteed Rate Field on July 10-995773460
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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.

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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.

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Kyle Seager Signed To The Seattle Mariners For $57.5 Million Over Three Years

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Kyle Seager #15 of the Seattle Mariners poses for a portrait during photo day at Peoria Stadium on February 18, 2019 in Peoria, Arizona-1130523721
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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.

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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.

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Zack Greinke Signed To The Arizona Diamondbacks For $104.5 Million Over Three Years

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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.

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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.

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Daisuke Matsuzaka Signed To The Boston Red Sox For $52 Million Over Six Years

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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).

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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.

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Carlos Beltran Signed To The New York Yankees For $45 Million Over Three Years

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Carlos Beltran #36 of the New York Yankees hits hit career 400th home run in the sixth inning against the Chicago White Sox at Yankee Stadium on May 15, 2016 in the Bronx borough of New York City-531637332
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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.

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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.

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Matt Kemp Signed To The Los Angeles Dodgers For $160 Million Over Eight Years

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Matt Kemp #27 of the Los Angeles Dodgers flips his bat after a fly ball out during the MLB game against the Arizona Diamondbacks at Chase Field on September 12, 2012 in Phoenix, Arizona-151896032
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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.

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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.

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A.J. Burnett Signed To The New York Yankees For $82.5 Million

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A.J. Burnett #34 of the New York Yankees reacts after giving up a three-run home run to Bengie Molina #11 of the Texas Rangers in the top of the sixth inning in Game Four of the ALCS during the 2010 MLB Playoffs at Yankee Stadium on October 19, 2010 in the Bronx borough of New York City-105756481
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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.

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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.

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Jayson Werth Signed To The Washington Nationals For $126 Million Over Seven Years

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Jayson Werth #28 of the Washington Nationals tosses his bat after being walked in the first inning against the San Francisco Giants during Game Four of the National League Division Series at AT&T Park on October 7, 2014 in San Francisco, California-456815870
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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.

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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.

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Carlos Lee Signed To The Houston Astros For $100 Million Over Six Years

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Carlos Lee #45 of the Houston Astros talks with the first base umpire Brian Knight #91 at Minute Maid Park on May 16, 2012 in Houston, Texas-144642141
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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.

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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.

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Nick Swisher Signed To The Cleveland Indians For $56 Million Over Four Years

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Nick Swisher #33 of the Cleveland Indians walks in the dugout after striking out in the sixth inning of the game against the Detroit Tigers at Comerica Park on June 8, 2013 in Detroit, Michigan. The Tigers defeated the Indians 6-4-170197637
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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.

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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.