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18 MLB Long-Term Contracts That Became Disastrous Investments

Long-term MLB Contracts That Turned Into Busts

Professional athletes are often signed for millions of dollars in hopes that they will lead their team to victory. In some cases, these long-term contracts become investments that are well worth it, while in other cases, they turn out to be bad deals.

In baseball, contracts can stretch over several years, and when things go wrong, teams are left with the consequences. In this article, we’ll take a look at some of the long-term contracts in Major League Baseball that turned into busts.

Jacoby Ellsbury – Seven-year/$153 million contract, New York Yankees

In 2013, the Yankees signed Jacoby Ellsbury to a seven-year contract, hoping that he would help them win another championship. However, Ellsbury struggled with injuries throughout his tenure with the team.

In 2017, he suffered a concussion and missed the entire season. The following season, he returned to play only 19 games due to hip injuries.

Ellsbury was released by the Yankees in 2019, but still earned over $21 million from the contract. Kenji Johjima – Three-year/$24 million contract, Seattle Mariners

The Seattle Mariners signed Kenji Johjima to a three-year contract worth $24 million in 2005.

Johjima showed promise as a catcher but was unable to live up to expectations. He struggled to adjust to the MLB’s pitching style and had trouble with his hitting.

After three years, the Mariners decided to end the contract early and paid the remaining $16 million to buyout the last year of his contract. Chris Davis – Seven-year/$161 million contract, Baltimore Orioles

In 2016, the Baltimore Orioles signed Chris Davis to a seven-year contract worth $161 million.

Davis was coming off a good season, during which he hit 47 home runs. However, after signing the contract, he struggled to keep his performance levels up.

In 2018, Davis hit .168 and continued to struggle the following year, hitting .179. Despite the struggling numbers, Davis is still under contract until 2022 and earns an average salary of over $21 million per season.

Ryan Howard – Five-year/$125 million extension, Philadelphia Phillies

Ryan Howard was in the prime of his career in 2010, when he signed a five-year contract extension worth $125 million with the Philadelphia Phillies. However, due to injuries, he struggled to play at his previous levels and often sat out due to his declining performance.

The Phillies eventually traded him to the Texas Rangers in 2016 after he hit .184 over 112 plate appearances. Mo Vaughn – Six-year/$80 million contract, Anaheim Angels

Mo Vaughn was a great hitter and won the AL MVP award in 1995.

He signed with the Anaheim Angels in 1999 for six years, worth $80 million. However, he struggled with injuries and saw his playing time decrease over the years.

After three seasons with the Angels, Vaughn retired due to medical reasons, but the Angels continued to pay him $15.2 million until 2008. Juan Gonzalez – Two-year/$24 million deal, Texas Rangers

In 2002, Juan Gonzalez signed a two-year contract with the Texas Rangers worth $24 million.

However, he was unable to replicate his MVP-winning form, and struggles on the field only compounded by his frequent injuries. Gonzalez played only 152 games in two years with the Rangers and hit just 35 home runs before leaving in free agency.

B.J. Upton – Five-year/$72.5 million, Atlanta Braves

In 2013, the Atlanta Braves signed B.J. Upton to a five-year contract worth $72.5 million. However, Upton was unable to keep up his performance levels and over the next two years, had a batting average of .198.

The Braves traded him to the San Diego Padres in 2014 but are still paying $5.2 million per year until 2020. Julio Lugo – Four-year/$36 million contract, Boston Red Sox

Julio Lugo was signed by the Boston Red Sox in 2007 for $36 million over four years.

While he started well, hitting .385 in his first seven games, his performance gradually declined. By 2009, he had lost his starting short-stop position and was released by the team in 2010.

Vince Coleman – Four-year/$12 million contract, New York Mets

In 1990, Vince Coleman was signed by the New York Mets for four years at a cost of $12 million. Coleman struggled to adapt to his time with the Mets, and his statistics showed it.

His stolen base percentage dropped, and he was unfortunately sentenced to community service after accidentally hitting a group of reporters with a firecracker. The Mets released him in 1993.

Jason Bay – Four-year/$66 million contract, New York Mets

Jason Bay signed with the New York Mets in 2009 to a four-year contract worth $66 million. Despite his success in the prior season with the Red Sox, where he hit 36 home runs and 119 RBIs, Bay was riddled with injuries and only played in 288 games with the Mets, allowing him the opportunity to finish his contract with the team as one of the worst investments in franchise history.

Bobby Bonilla Deferred payments contract, New York Mets

While not the norm for bad contracts, the deferred payments made in this deal made it notable. In 2000, Bobby Bonilla had a $5.9 million option on his contract with the New York Mets.

Rather than exercising the option, the team bought him out for $5.9 million while agreeing to pay him $1.19 million per year from 2011 until 2035. The deal was made due to a clause that allowed for deferred payments, meaning that Bonilla gets $1.19 million per year for not playing.

Jeffrey Hammonds – Three-year/$21 million contract, Milwaukee Brewers

Jeffrey Hammonds signed a three-year contract with the Milwaukee Brewers worth $21 million. The Brewers hoped that he would improve their fortunes, but Hammonds never lived up to his contract.

He was constantly injured and batted .247 during his tenure before being released by the Brewers. Milton Bradley – Three-year/$30 million contract, Chicago Cubs

In 2009, the Chicago Cubs signed Milton Bradley to a three-year contract worth $30 million.

However, Bradley’s time with the Cubs was filled with controversies, including a confrontation with an umpire and a physical altercation with a teammate. The Cubs traded him to the Seattle Mariners for Carlos Silva, and Bradley retired within two years of signing the contract.

Gary Matthews Jr. – Five-year/$65 million contract, Los Angeles Angels

In 2007, Gary Matthews Jr. signed a five-year deal with the Los Angeles Angels worth $65 million. However, Matthews struggled throughout his time with the team, hitting only .248 in his first season with the team and just .250 over the remainder of his tenure.

The Angels eventually traded him to the New York Mets in 2010. Carl Crawford – Seven-year/$142 million deal, Boston Red Sox

In 2011, the Boston Red Sox signed Carl Crawford to a seven-year contract worth $142 million.

However, injuries prevented Crawford from reaching his full potential. He was traded to the Los Angeles Dodgers in 2012 after only playing in 130 games for the Red Sox and hitting only .260.

Yasmany Tomas – Six-year/$68.5 million deal, Arizona Diamondbacks

In 2014, the Arizona Diamondbacks signed Yasmany Tomas to a six-year contract worth $68.5 million. Tomas struggled during his time with the team, hitting only .268 with 48 home runs over four seasons.

The Diamondbacks released him in 2018. Josh Hamilton – Five-year/$125 million, Los Angeles Angels

In 2013, the Los Angeles Angels signed Josh Hamilton to a five-year contract worth $125 million.

However, Hamilton struggled with injuries and poor performances, resulting in only 240 games played and a .255 batting average with the Angels. He was traded back to the Texas Rangers in 2015.

David Wright – Eight-year/$138 million deal, New York Mets

In 2012, the New York Mets signed David Wright to an eight-year contract worth $138 million. Wright was a star player for the Mets, but over the years, he was subjected to several injuries that limited his playing time.

He missed two full seasons and played in only 38 games between 2016 and 2018. Wright retired in 2018, but the Mets still have to pay him $15 million in 2020.

Pablo Sandoval – Five-year/$95 million deal, Boston Red Sox

In 2014, Pablo Sandoval signed a five-year contract worth $95 million with the Boston Red Sox. However, Sandoval was benched in the first season and was plagued by injuries and weight issues.

He played only a handful of games in his second season before being released. The Red Sox are still paying his salary until the end of the contract.


In conclusion, long-term MLB contracts can be a risk for any team. As the contracts become more lucrative and the stakes become higher, it’s essential to think critically and strategically about the player’s previous performances and future potential.

While some of these contracts may have seemed like a good idea at the time, in hindsight, they were not worth the investment. The impact of these bad contracts can be felt for years, often limiting teams’ financial capacities and players’ careers.

In summary, some of the long-term MLB contracts in Major League Baseball have turned into busts. Players who show promise and perform well in previous seasons are not always a safe bet for a long-term contract.

Signing players comes with inherent risks, and teams need to think critically and strategically before making long-term deals to ensure they get the performance they are paying for. Bad contracts can have detrimental effects on teams’ financial capacities and players’ careers.

It is essential to acknowledge the risks associated with long-term contracts and make informed decisions.

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