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The worst contracts in MLB history

The explosion of cash flows recently in MLB has caused plenty of teams to overspend on contract extensions and in free agency. Here's a look at the worst contracts in the history of MLB.

 
1 of 28

Homer Bailey: six years, $105 million

Homer Bailey: six years, $105 million
Charles LeClaire / USA Today Sports Images

The small-market Reds curiously signed Bailey to a massive six-year deal before the 2014 season after consecutive 200-plus inning seasons. He was hurt for most of the deal. The right-hander threw 145.2 innings with a 3.71 ERA in 2014, but he made a total of 46 starts with a 6.25 ERA over the next four years. It's hardly the performance the Reds expected after giving Bailey ace money. The Reds traded him last offseason.

 
2 of 28

Jason Bay: four years, $66 million

Jason Bay: four years, $66 million
Doug Benc / Getty Images

Coming off an outstanding 2009 season in Boston with a career-high 36 home runs and 119 RBI, the Mets signed Bay to an ill-fated four-year deal. The Canadian outfielder averaged .229-9-36 with a .688 OPS in 89 games over the life of the deal, finishing out the contract (and his career) in Seattle after the Mets released him in November of 2012.

 
3 of 28

Kevin Brown: seven years, $105 million

Kevin Brown: seven years, $105 million
Vincent Laforet / Getty Images

Brown was the first MLB player to break the $100 million barrier, signing a seven-year deal as he approached his age-34 season going into 1999. The first two years of the deal were good for both sides, as he finished sixth in the Cy Young voting in consecutive years. But then injuries struck the right-hander. He made more than 22 starts only once over the last five seasons of the contract, averaging 119 innings with a 3.58 ERA. Brown was traded to the Yankees before the 2004 season and failed to stay healthy over his final two seasons in pinstripes.

 
4 of 28

Miguel Cabrera: eight years, $248 million

Miguel Cabrera: eight years, $248 million
Rick Osentoski / USA Today Sports Images

Cabrera already started to show signs of decline when the Tigers gave him an eight-year extension in 2016. He had one last big year in 2016 but has been subpar since then. He's averaged only .270-10-47 with a .749 OPS over the last three seasons, shifting to DH and missing significant time due to injuries.

 
5 of 28

Rusney Castillo: seven years, $72.5 million

Rusney Castillo: seven years, $72.5 million
Steve Mitchell / USA Today Sports Images

In recent years, many teams have made big investments on Cuban players that have paid off. This wasn't one of them. Boston signed Castillo to a seven-year deal in August of 2014, but the team has only 99 games from Castillo over six seasons to show for it. Castillo has been stuck at Triple-A Pawtucket for most of the deal.

 
6 of 28

Yoenis Cespedes: four years, $110 million

Yoenis Cespedes:  four years, $110 million
Brad Penner / USA Today Sports Images

The Mets rewarded Cespedes with a four-year deal in 2017 after he hit 31 home runs and made an All-Star appearance in 2016. He's missed more time than he's played through the first three seasons of the deal and sat for all of 2019 due to heel and ankle injuries.

 
7 of 28

Carl Crawford: seven years, $142 million

Carl Crawford: seven years, $142 million
Elsa / Getty Images

Boston thought it was getting an elite offensive and defensive left fielder when it signed Crawford to a seven-year deal in 2011, but he was far from it. He struggled at the plate in his first season, hitting just .255-11-56 with 18 steals and a .694 OPS in 130 games. The following year Crawford played only 31 games due to injury, struggled to stay healthy for the remainder of his career and was traded to the Dodgers in a blockbuster deal before 2013. Crawford played only six years of the seven-year deal, averaging .271-5-29 with 12 steals in 80 games per season.

 
8 of 28

Chris Davis: seven years, $161 million

Chris Davis: seven years, $161 million
Evan Habeeb / USA Today Sports Images

Davis is a microcosm of the current state of the Orioles organization. The first baseman signed a seven-year deal with Baltimore before the 2016 season, but his play has deteriorated to the point that he's arguably the worst player in baseball. After hitting .221-38-84 in his first season of the contract, Davis hit just .215-26-61 (.732 OPS) in his second season, .168-16-59 with a .539 OPS  in 522 plate appearances during 2018 and .179-12-36 with a .601 OPS in 2019. Only three more years to go...

 
9 of 28

Darren Dreifort, five years, $55 million

Darren Dreifort, five years, $55 million
Jeff Gross / Getty Images

Dreifort's big contract with the Dodgers is overshadowed by Kevin Brown's mega deal, but the Dodgers got even less out of this right-hander. Signed before the 2001 season, Dreifort posted a 5.13 ERA in 16 starts in his first season, missed all of 2002 to Tommy John surgery and made only 10 starts in 2003, followed by 60 relief appearances with a 4.44 ERA in 2004.

 
10 of 28

Jacoby Ellsbury, seven years, $153 million

Jacoby Ellsbury, seven years, $153 million
Kim Klement / USA Today Sports Images

The Red Sox lost Ellsbury to the rival Yankees in 2014, but it's worked in Boston's favor. The outfielder has been a mediocre, overpriced contributor for the Bronx Bombers for the life of his contract. He peaked in 2014, hitting .271-16-70 with 39 steals and a .747 OPS but averaged just .261-8-43 with 21 steals in 124 games over the next three seasons and missed all of 2018 and 2019 due to injury. Ellsbury has one year remaining on his contract, but the Yankees aren't counting on him.

 
11 of 28

Prince Fielder: nine years, $214 million

Prince Fielder: nine years, $214 million
Leon Halip / Getty Images

Fielder left Milwaukee to sign a nine-year deal with Detroit in 2012. His performance fell off after his first year of the deal, hitting .279-25-106 with an .819 OPS in 2013. Even more significantly, Fielder alienated Tigers fans with his words in the media and was traded to the Rangers for Ian Kinsler and cash. Fielder played only 42 games in his first year of the deal, made an All-Star appearance in 2015 and hit .305-23-98 but was shut down after 89 games played the following season with a career-ending neck injury.

 
12 of 28

Alex Gordon: four years, $72 million

Alex Gordon: four years, $72 million
Brian Spurlock / USA Today Sports Images

Seemingly as a "thank you" for helping the Royals win the World Series in 2015, KC re-signed Gordon to a four-year, $72 million deal. He imploded immediately, hitting just .220-17-40 in the first year of the contract, and it's only gotten worse for him. While he did win three Gold Gloves in the four seasons, Gordon averaged .237-13-54 with a .686 OPS at the plate.

 
13 of 28

Josh Hamilton: five years, $125 million

Josh Hamilton: five years, $125 million
Victor Decolongon / Getty Images

The Angels added Hamilton to Mike Trout and Albert Pujols in 2013, signing him for big money after he hit 43 home runs for Texas. The imposing lineup never really came to fruition. Hamilton hit just .250-21-79 with a .739 OPS and played only 89 games the following year. He had a falling out with the organization after a shoulder injury and drug relapse and was traded back to Texas in 2015. He played 50 games for the Rangers in 2015, but that was the last we saw of Hamilton in the majors.

 
14 of 28

Mike Hampton: six years, $80 million

Mike Hampton: six years, $80 million
Brian Bahr / Getty Images

Hampton signed a six-year deal with the Rockies in 2001 to pitch at Coors Field. What could go wrong? The lefty posted a 5.75 ERA in two seasons with Colorado before getting traded to Atlanta. Over the next three seasons, Hampton was at least back to respectability with a 3.96 ERA over 72 starts, finishing out the contract sidelined due to an elbow injury. 

 
15 of 28

Jason Heyward: eight years, $184 million

Jason Heyward: eight years, $184 million
Jerry Lai / USA Today Sports Images

Heyward still has time to prove he deserved the eight-year deal the Cubs gave him in 2016, but it's not looking good through four seasons. While he's still elite defensively, Heyward has apparently forgotten how to hit, averaging just .252-12-57 with a .711 OPS over the first four seasons of his contract. His speed and defense also clearly slipped, so it looks possible that the last half of the contract could be an even bigger disaster.

 
16 of 28

Ryan Howard: five years, $125 million

Ryan Howard: five years, $125 million
Derik Hamilton / USA Today Sports Images

With two years remaining on his contract, the Phillies inexplicably gave Howard a five-year, $125 million extension on top of that in 2010. The new contract started in 2012, exactly when his extreme decline started. Over the last five seasons of his career, Howard averaged .226-19-66 with a .719 OPS and played more than 129 games only once. By the end of the deal, the Phillies World Series teams he played on were a distant memory.

 
17 of 28

Joe Mauer: eight years, $184 million

Joe Mauer: eight years, $184 million
Kim Klement / USA Today Sports Images

The Twins extended Mauer when he was a catcher and MVP candidate, but concussions caused him to move over to first base. The 2009 MVP dropped off considerably at the plate after signing the deal, averaging .290.8-56 with a .777 OPS during the eight seasons. That production isn't bad for a catcher, but he moved to first base full time after only three seasons and severely handicapped the small-market Twins financially.

 
18 of 28

Chan Ho Park: five years, $65 million

Chan Ho Park: five years, $65 million
Jonathan Daniel / Getty Images

Shortly after signing Alex Rodriguez, the Rangers also signed Park to a five-year deal in 2002. He was an innings eater for the Dodgers in his two seasons before free agency but posted an ERA above 5.00 in four straight seasons with the Rangers before getting traded to the Padres for Phil Nevin in 2005.

 
19 of 28

Albert Pujols: 10 years, $240 million

Albert Pujols: 10 years, $240 million
Rick Scuteri / USA Today Sports Images

Pujols shocked the baseball world when he left St. Louis and signed a 10-year deal with the Angels in 2012. He immediately declined at age 32, posting an .859 OPS in his first season and hasn't topped .790 since then. He's really struggled over the last three seasons, averaging .243-22-86 with a .700 OPS, and the Angels still have to pay Pujols for two more seasons.

 
20 of 28

Alex Rodriguez, 10 years, $252 million

Alex Rodriguez, 10 years, $252 million
Gary Barber / Getty Images

The Rangers made headlines when they signed A-Rod to the biggest contract in sports history in 2001. While Rodriguez delivered on the field, leading the AL in home runs in each of his first three seasons, the Rangers never won more than 73 games due in large part to the fact that they couldn't afford to put viable players around him. Rodriguez was traded to the Yankees after three seasons and did win three MVP Awards during the deal.

 
21 of 28

Pablo Sandoval: five years, $95 million

Pablo Sandoval: five years, $95 million
Eric Hartline / USA Today Sports Images

Given his history of being out of shape, Sandoval's huge five-year contract with Boston in 2015 was a head-scratcher at the time. True to form, Sandoval was out of shape and struggled in his first season with Boston, hitting only .245-10-47 with a .658 OPS, and he missed nearly all of his second season with a shoulder injury. Boston cut its losses by releasing Sandoval in July of 2017.

 
22 of 28

James Shields: four years, $75 million

James Shields: four years, $75 million
Chris Humphreys / USA Today Sports Images

One of the most durable and reliable pitchers in baseball before signing a four-year deal with the Padres in 2015, "Big Game James" immediately fell into decline after he got his money. He had a 3.91 ERA in 33 starts in his first season with San Diego and then went 5-19 with a 5.85 ERA the following year, eventually getting traded after ownership berated him in the media. Shields finished out the deal with the White Sox, posting a 5.23 ERA in 21 starts in 2017, but he improved his ERA to 4.53 in 204.2 innings in 2018 after lowering his arm angle.

 
23 of 28

Yasmany Tomas: six years, $68.5 million

Yasmany Tomas: six years, $68.5 million
Steve Mitchell / USA Today Sports Images

A power hitter who was limited defensively, Tomas signed a huge six-year deal with the Diamondbacks in 2015 after leaving Cuba. He hit just .273/.305/.401 in his first season before launching 31 home runs in his season year. Tomas declined to .241/.294/.464 in 180 plate appearances in 2017 and has seen little time in the majors since then.

 
24 of 28

Melvin Upton: five years, $72.5 million

Melvin Upton: five years, $72.5 million
Jim McIsaac / Getty Images

Known as "B.J." when he signed a five-year deal with Atlanta in 2013, Upton's play immediately imploded after getting paid. He hit just .194-9-26 with a .557 OPS at age 28 and didn't show much improvement in 2014, hitting .208-12-35 with a .620 OPS. Atlanta decided a change of scenery was necessary after only two seasons, trading Upton to San Diego in early 2015 before he was traded to Toronto the following year and eventually released. Upton hasn't appeared in the majors since 2016.

 
25 of 28

Vernon Wells: seven years, $126 million

Vernon Wells: seven years, $126 million
Jay Gula / Getty Images

Wells was a star after the 2006 season in Toronto and was paid like one by the Jays. After hitting .303-32-106 in 2006, he declined to .245-16-80 with an OPS that fell nearly 200 points. He had a bit of a rebound in 2008, with an .840 OPS, but he missed significant time to injury. Wells was inconsistent from year to year for the rest of the contract, posting one more .800-plus OPS, 30 home run season in 2010 but posting a sub-.700 OPS after getting traded to the Angels and later the Yankees from 2011-13.

 
26 of 28

David Wright: eight years, $138 million

David Wright: eight years, $138 million
Brad Penner / USA Today Sports Images

Injuries robbed Wright of what might have been a Hall of Fame career. He made his last of seven All-Star appearances after signing his new contract in 2013 and then regressed to just .269-8-63 with a .698 OPS in 2014. He played only 77 games over the next four seasons due to a chronic neck and shoulder problem, retiring after appearing in the last series of the 2018 season.

 
27 of 28

Jordan Zimmermann: five years, $110 million

Jordan Zimmermann: five years, $110 million
Jeff Hanisch / USA Today Sports Images

Even despite declining velocity and strikeouts, the Tigers struck early in the 2015-16 offseason by giving Zimmermann a five-year deal. He's yet to make 30 starts in a season during the first four years of the contract, positing a cumulative 6.91 ERA as his velocity and strikeouts have continued to implode.

 
28 of 28

Barry Zito: eight years, $126 million

Barry Zito: eight years, $126 million
Christian Peterson / Getty Images

San Francisco shocked the baseball world when it emerged as the winners of the Zito sweepstakes in 2007. The lefty never posted an ERA below 4.00 during the contract, finishing the deal with a cumulative 4.62 ERA and struggling to stay healthy in two of the last three seasons. The Giants did win two World Series during his tenure despite the contract, thanks to great contributions from young players like Buster Posey, Tim Lincecum, Madison Bumgarner and Matt Cain.

Seth Trachtman is a fantasy sports expert and diehard Kansas City Chiefs fan still hoping for a Super Bowl win during his lifetime. He doesn't often Tweet, but when he does, you can find him on Twitter @sethroto.


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