We all have regrets. Major League Baseball teams have more than a few, as Major league teams often bite off more than they can chew when they sign a player to a long term contract.

Teams believe when they sign a player to a big contract that they’ll receive a great return on their investment each passing season. They couldn’t be more wrong. The likelihood that players perform at the same level each season is nearly impossible. Players get old, therefore injuries will increase. Once the injuries come, productivity will likely go down. Though stints on the disabled list, multiple surgeries and lackluster seasons are a chance MLB owners are willing to take in order to acquire a big name free agent.

It’s usually after a stretch of stellar performance when teams will break out the checkbook and sign a player to a big contract. A brief stint of success can warrant a contract exceeding more than half a decade in time and more money than average people can think to do with in three lifetimes.

Another reason for ludicrous contracts is the fear of losing a star. When players are drafted and become a star in a small market organization, teams will pay top dollar to keep them from leaving.

The following are the worst contracts in MLB history.

20. Mo Vaughn – Anaheim Angels – 6 Years/$80 Million 

via complex.com

via complex.com

Having a massive power hitter on your ball club is always good. Having a giant like Mo Vaughn is a bonus. In 1998, he signed a six-year $80 million contract with the Anaheim Angels, which at the time was the largest contract in baseball history. Things didn’t last long in Anaheim for Vaughn, as just two seasons into the massive contract he was traded to the New York Mets.

In his two seasons in New York, he hit only 29 home runs. In 2003, Vaughn suffered a significant knee injury which he never recovered from. However the career ending injury didn’t free the Mets from paying his $47 million in remaining salary.

19. Daisuke Matsuzaka – Boston Red Sox – 6 Years/$52 Million 

shutterstock_52520722

In 2007, the Boston Red Sox took a plunge and signed Japanese pitching phenom Daisuke Matsuzaka to a 6-year, $52 million contract.

Matzusaka’s first year in Boston was actually sensational. He won 15 games and came in fourth in Rookie of the Year voting. He also helped the Red Sox to their second World Series championship in three years. Success only went up the following season. In 2008, he won 18 games and finished fourth in Cy Young award voting.

The final four years of Matsuzaka’s contract were anything but stellar and were riddled with injuries. After the 2008 season, he went on to win 17 more games for the Red Sox and his ERA rose to above 5.50.

18. Carlos Beltran – New York Yankees – 3 Years/$45 Million 

Reinhold Matay-USA TODAY Sports

Reinhold Matay-USA TODAY Sports

Coming up in the clutch is something Carlos Beltran isn’t necessarily known for. The outfielder’s career has been summed up by one pitch he failed to swing at as a member of the New York Mets.

When Beltran returned to New York as a member of the Yankees, the organization hoped he would help them reach the postseason. Sadly, the once great Beltran has fallen way short of expectations while playing in pinstripes.

In the two seasons he’s played in the Bronx, he’s missed over 80 games due to injury. The power has decreased significantly as well. The once great slugger has only hit 34 home runs and 116 RBIs while maintaining a .256 batting average.

17. Matt Kemp – Los Angeles Dodgers – 8 Years/$160 Million 

Mark J. Rebilas-USA TODAY Sports

Mark J. Rebilas-USA TODAY Sports

Baseball teams show their devotion to franchise players by issuing massive contract extensions. In 2011, the Dodgers demonstrated their support of Matt Kemp by signing him to a franchise record contract extension.

After Kemp’s stellar season in 2011, which earned him the gigantic deal, his numbers fell drastically. His batting average dropped from .324 to .270 in 2013. In 2015, the Dodgers had enough and traded him to the division rival San Diego Padres.

In his first season with San Diego, his average plummeted further to .265. He is under contract with the Padres until 2020, earning more than $20 million a year.

16. Carl Crawford – Boston Red Sox – 7 Years/$142 Million 

Jake Roth-USA TODAY Sports

Jake Roth-USA TODAY Sports

Carl Crawford was sure to leave the small market Tampa Bay Rays for a large scale contract. The Red Sox made playing left field in front of the Green Monster the most attractive destination with a seven-year deal worth $142 million.

Crawford was relentlessly heckled by Red Sox fans for his abysmal performance. He missed 32 games in his first season due to injury and held an average of .255 a steep decline from his previous season where he hit .307. The following year he only payed 31 games due to multiple surgeries. After two horrendous seasons in Boston, Crawford was traded to the Dodgers in 2013 as a part of a multiplayer deal.

Crawford continues to miss large chunks of seasons due to injuries. Though his batting average fell, his contract remains high earning close to $21 million a year through the 2017 season.

15. A.J. Burnett – New York Yankees – 5 Years/$82.5 Million 

Charles LeClaire-USA TODAY Sports

Charles LeClaire-USA TODAY Sports

You can never have enough pitching. The Yankees followed this philosophy by signing A.J. Burnett to a five-year deal in 2009. The season ended in success earning the Yankees their 27th World Championship, but things were just beginning to go downhill for the overpaid right hander.

Burnett finished the 2009 season winning 13 games. The following two seasons were anything but stellar, Burnett won 21 games combined and his ERA rose to 5.20. After the 2011 season, the Yankees traded Burnett to the Pittsburgh Pirates and agreed to pay more than half of the remaining salary.

14. Ryan Howard – Philadelphia Phillies – 5 Years/$125 Million 

Jonathan Dyer-USA TODAY Sports

Jonathan Dyer-USA TODAY Sports

Having a power hitter can be a big boost to any lineup. Ryan Howard sure brought the power to the National League when the Philadelphia Phillies won five consecutive Division Championships and reached back-to-back World Series (winning one).

The Phillies definitely wanted to keep Howard, so they secured him with a five-year extension worth $125 million. Howard’s first year of the deal was anything but powerful. The first baseman was injured most of the season only able to play 80 games. The home run count has gone down too. The slugger who once hit nearly 50 a season has yet to have a 25 plus home run season since signing the extension in 2013.

The Phillies sure seem to regret the contract. In 2015, they offered to trade Howard and pay $25 million of his contract, nearly half of what’s remaining on the absurd deal. There were no takers…

13. Jayson Werth – Washington Nationals – 7 Years/$126 Million 

Brad Mills-USA TODAY Sports

Brad Mills-USA TODAY Sports

For years, the Washington Nationals were at the bottom of the league in all categories. In 2010 they made a move by bringing Jayson Werth from the division rival Philadelphia Philies over to D.C. on a 7-year deal.

Werth brought a new face to the Nationals. However, since signing the lucrative deal in 2010, Werth has been a below average player making above average money.In the five years the slugger has been in Washington, he’s only hit 78 home runs and has had multiple shortened seasons due to injuries.

Werth has had off field trouble as well. In January of 2015, he was arrested for reckless driving. The right fielder still has two seasons left on his contract, most likely to be filled with long DL stints and low productivity.

12. Carlos Lee – Houston Astros – 6 Years/$100 Million 

shutterstock_99989432

When the Houston Astros signed Carlos Lee in 2007 to a six-year deal, it was huge news. The slugger who spent a majority of his career in the American League was taking his talents to the National League.

The first three years of the contract, Lee was magnificent, hitting around  30 home runs a season and racking up over 100 RBIs. After the 2009 season, the slugger’s batting average fell. The once .300 hitter became a .246 hitter. His home run total dropped too, as he barely hit over 20 home runs a season.

In Lee’s six years in Houston, the team never reached the postseason and the first basemen was elected to the All Star game one time. In 2012, Lee was traded to the Miami Marlins. After the 2012 season ended, Lee retired from professional baseball.

11. Josh Hamilton – Anaheim Angels – 5 Years/$125 Million 

Robert Hanashiro-USA TODAY Sports

Robert Hanashiro-USA TODAY Sports

When Hamilton left Texas for Los Angeles in 2013, the Angels became an instant contender. Hamilton would be in the same lineup with future Hall of Famer Albert Pujols and rookie sensation Mike Trout.

Sadly, Hamilton was horrid in his first two seasons with the Angels, only hitting 31 home runs while batting .255. When the Angels reached the postseason in 2014. he went 0-13 in three games played.

In 2015, he sadly relapsed into drug addiction and was suspended by the Angels organization. He was soon traded back to the Texas Rangers, where he is set to make over $25 million a year for the next two seasons.

10. Chan Ho Park – Texas Rangers – 5 Years – $65 Million 

shutterstock_61124644

When Chan Ho Park became a free agent after the 2001 season, the Texas Rangers jumped on the opportunity to sign him. The Korean right hander signed a five-year deal worth $65 million.

Park joining the Rangers fell way short of expectations. In 2002, in his first season with the team, he recorded only nine wins maintaining an ERA of 5.75. The remaining years of Park’s contract were filled with injuries. The next three years in Texas Park went on to win only 13 games while holding an ERA around 6.00.

In 2005, Park was traded mid-season to the San Diego Padres where he finished the season with a record of 4-3 with an ERA of 5.91.

9. Nick Swisher – Cleveland Indians – 4 Years/$56 million 

Jerome Miron-USA TODAY Sports

Jerome Miron-USA TODAY Sports

Nick Swisher has always been known for his fun personality. After his contract with the Yankees ended, he charmed the Cleveland Indians into giving him a massive four-year deal.

In Swisher’s second season with the Indians, he batted .208 playing in 97 games due to rampant injuries. Swisher’s power diminished as well, hitting only eight home runs and bringing in 42 RBIs.

In the middle of the 2014 season, Swisher had arthroscopic surgery on both of his knees. The surgery ended his season that year and he only managed 30 games the following season before being traded to the Braves. In March of 2016, the Braves released Swisher, still owing him more than $15 million in unpaid salary.

8. Kei Igawa – New York Yankees – 5 Years/$20 Million 

via thebostonjam.com

via thebostonjam.com

The Yankees have always competed with their division rival, the Boston Red Sox. In 2007. they competed for the signing of Japanese pitcher Kei Igawa, who signed with the Yankees on a 5-year deal. The deal was similar to Red Sox’s Japanese pitcher Daiskue Matzusaka ‘s deal, who was signed by the Red Sox on a six-year deal.

In addition to Igawa’s contract, the Yankees also paid over $26 million for the bidding rights to sign the Japanese left hander. In his first season, Igawa had a record of 4-3 and an of ERA of 6.25, constantly being knocked around by opposing lineups.

The following season he started only one game and finished the season playing for the team’s minor league affiliate Scranton/Wilkes Barre Yankees. Igawa never pitched in the majors again and collected his remaining salary while pitching in the minor leagues.

7. Alex Rodriguez – New York Yankees – 10 Years/$275 Million 

Steve Mitchell-USA TODAY Sports

Steve Mitchell-USA TODAY Sports

The Yankees have made a few appearances on this list and Alex Rodriguez’s deal is one contract I’m sure they’d love to rescind. In 2008, the Yankees signed Rodriguez to the largest contract in professional sports history at the time, at $275 million over 10 years.

The contract would pay the three-time MVP into his early forties. In 2009, Rodriguez helped the Yankees to their 27th World Series championship. Since then Rodriguez has had multiple season ending injuries and has been in the media more than on the field.

The once great slugger who hit well over 100 RBIs per season has failed to hit over 90 RBIs since 2010. In 2014, he served a season long suspension for breaking the league’s substance abuse policy.

6. Mike Hampton – Colorado Rockies – 8 Years/$121 Million 

via rantsports.com

via rantsports.com

Signing a pitcher to a deal longer than six years is a bit much. Signing a pitcher to eight years is downright ridiculous. The Colorado Rockies showed how daring they were in 2001 when they signed Mike Hampton to a eight-year deal.

In Hampton’s two seasons with the Rockies, he won 21 out of the 62 games that he started. The Rockies traded Hampton to the Atlanta Braves in 2003 with six years remaining on the contract.

Hampton finished out the contract in Atlanta. His time there was sub-par and injury ridden. Two of the seasons, he was there he was completely sidelined due to Tommy John surgery.

5. Jonathan Papelbon – Philadelphia Phillies – 4 Years/$50 Million 

Eric Hartline-USA TODAY Sports

Eric Hartline-USA TODAY Sports

Players who are overpaid can be a burden on a team when they perform poorly. This was something the Phillies didn’t take into consideration when they signed closer Jonathan Papelbon to a 4-year $50 million contract.

Papelbon earned close to 40 saves each year, but the Phillies paid the All Star closer to basically finish games falling way short of the post season almost every year.

In 2015, when the Phillies were on pace to lose more than 100 games, he was traded to the Washington Nationals. Later that season, he was suspended for getting into an altercation with outfielder Bryce Harper. Papelbon went on to file a grievance with the team and is still owed $11 million from his salary with the Phillies which Washington took on after completing the trade.

4. Carl Pavano – New York Yankees – 4 Years/$39 Million 

via riveraveblues.com

via riveraveblues.com

The Yankees signed Carl Pavano to a multi-year deal in 2005 after a successful stint with the Florida Marlins. Earning nearly $10 million a season, Pavano had big expectations to meet.

Pavano’s time with the Yankees can be classified as non-existent. In the four years with the organization, Pavano won only nine games and held an ERA well over 4.00. Pavano missed the entire 2006 season and a majority of the 2007 season after opting into getting Tommy John Surgery.

In his final year in New York, he started only seven games winning 4 of them. He spent the majority of the year on the disabled list battling injuries.

3. Kevin Brown – Los Angeles Dodgers – 7 Years/$105 Million 

via dodgersnation.com

via dodgersnation.com

It’s a risk to sign a player in their mid-thirties to a large contract. In 1998, the Los Angeles Dodgers took a huge gamble signing 34 year old Kevin Brown to a 7-year deal.

Brown’s first few seasons in L.A. weren’t that bad, as he won more than 10 games each season and maintained an ERA below 3.00. After the 2002 season, Brown began to fall apart. The veteran pitcher faced multiple injuries and, in 2004, Brown was traded to the New York Yankees.

Brown’s most infamous moment with the Yankees came with him punching the wall of the dugout injuring his hand. In 2004, Brown performed poorly in the playoffs, as the Boston Red Sox hit him hard and ending up beating the Yankees to advance to the World Series.

2. Jason Bay – New York Mets – 4 Years/$66 Million

via bleacherreport.com

via bleacherreport.com

It was puzzling when outfielder Jason Bay left a hitter friendly ballpark in Boston to come to Citi Field to play for the Mets. Then it became obvious, money. Bay signed a 4-year, $66 million contract with the Mets to be their everyday left fielder.

In his first season, he appeared in only 95 games due to constant injuries. The following season he appeared in 112 games, but hit only 12 home runs and 57 RBIs, falling way short of expectations.

Bay became notorious among Mets fans and, when he appeared at the plate, he was often heckled more than the opposing team. In 2012, the Mets and Bay agreed to part ways, paying his contract off over time.

1. Bobby Bonilla –  New York Mets – 25 Years/$29 Million 

via nesn.com

via nesn.com

It’s strange to think that Bobby Bonilla would be on this list. He was never a superstar who put up big caliber numbers. It was in fact the mistake of Mets team ownership which has forced them to pay the outfielder $1.19 million a year through 2035.

After the 1999 season, Bonilla was still owed nearly $6 million by the Mets. He and his agent made an agreement with Mets owner Fred Wilpon. Bonilla wouldn’t take salary for a decade and in 2011 would be paid nearly $30 million over a span of 25 years.

Wilpon agreed to the deal because in 1999 instead of paying Bonilla, he had invested a large sum of the organization’s money with Bernie Madoff, who ended up running a massive ponzi scheme.

  • Ad Free Browsing
  • Over 10,000 Videos!
  • All in 1 Access
  • Join For Free!
GO PREMIUM WITH THESPORTSTER
Go Premium!

Videos