Top 10 Worst Signings in Major League Baseball History

Nothing makes the average sports fan become more enraged than a ridiculous contract. Many purist fans of the sport will think that any contract exceeding $20 million a year to play the peaceful game of baseball would be crazy, let alone the recent contracts given to Miguel Cabrera and Giancarlo Stanton that were in excess of $300 million over the life of the deal. Another factor that will enrage baseball fans of smaller market teams is the lack of a salary cap. When the annual salary of two players on the New York Yankees can surpass that of entire teams (Pittsburgh and Tampa Bay), it is easy to say that things need to change.

In the current landscape of baseball, there are more terrible contracts given simply because there are more $100 million contracts being awarded. Talented players like Freddie Freeman, Shin-Soo Choo, and Jayson Werth were all given contracts greater than $125 million in total and while these players may deserve to be paid well, some would argue not that well.

It doesn’t just mean that the contracts that are given today are the only terrible deals in baseball history, they just stand out more. Before the 1990 season, the Cleveland Indians decided to sign former MVP and All Star Keith Hernandez to a 2 year, $3 million deal. In 2014, that wasn’t a large number, but at the time, it was a lot of money to give a 36-year-old player, but in the end, he played in just 43 games with a .200 batting average.

Another notable contract that is often discussed is that of Bobby Bonilla, who hasn’t played since 2000, but from 2011 to 2035 will receive about $1.2 million per year from the New York Mets. This contract agreement came about when the Mets wanted to release Bonilla and instead of paying him the $5.9 million owed to him at the time, Bonilla and his agent worked out a deal where they would defer the payment with interest.

Let’s go ahead and take a look at the 10 worst contracts in Major League Baseball history and find out exactly why these deals were so bad.

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10 Chan Ho Park, 5 years, $65 million, 2002

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The Texas Rangers made Chan Ho Park one of the richest players in baseball when he became a free agent for the first time. He had spent the first eight years of his career with the Los Angeles Dodgers and was coming off his fifth straight season with at least 13 wins and had a combined record 75-49 during that time. The Rangers, looking to make waves in the baseball world the year after bringing Alex Rodriguez the season before, certainly received the short end of the stick in the Park deal. His career as a Ranger lasted parts of just four seasons, combining to go 22-23 with a 5.79 ERA.

9 Alex Rodriguez, 10 years, $252 million, 2001

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For the second straight listing, the Texas Rangers were the culprits behind one of the worst signings in Major League Baseball history. Alex Rodriguez received what was the biggest contract in the history of the sport and what is believed to be the beginning of the end when it came to reasonable contracts in the sport. The Rangers were hoping that Rodriguez would help bring them out of the gutters in the American League West division, but during his three years with the team, went just 216-270 and finished in last place each season. He would then be dealt to the New York Yankees,  The signing did bring some more fans to the ball park in Arlington, but in the end, it wasn’t worth the ink used to sign his checks each week.

8 B.J. Upton, 5 years, $75.25 million, 2012

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In what is one of the worst signings in the sport today, the Atlanta Braves signed B.J. Upton to this contract, uniting him with his brother Justin. It was supposed to be the beginning of a remarkable era in the history of the franchise, but instead, the Braves recently traded Justin, and wish they could do the same with B.J. In two seasons with the team, Upton has been one of the worst players in the league. He has batted just .198 with 21 home runs, 61 RBIs, 32 stolen bases and a puny .279 OBP. Most Atlanta fans are hoping to see the Braves unload his contract on some poor unsuspecting team, but the likelihood of that happening is quite small.

7 Johan Santana, 6 years, $137.5 million, 2008

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Johan Santana had just finished his tenure with the Minnesota Twins in 2008 when signed this contract with his new team, the New York Mets. With all that money guaranteed to him by the Mets, one would have expected Santana to get close to 200 starts under his belt. Instead, he made every start he was scheduled for just once, missed two complete seasons and was just 46-34. His ERA was on point in the National League as it was when he was with the Twins, but the fact that he made just 109 starts with the Mets makes this one of the worst signings in Major League Baseball history.

6 Albert Belle, 5 years, $65 million, 1998

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In the 1990s, Albert Belle was one of the best players in the sport of baseball. He finished in the top 10 in the Most Valuable Player race five times in six seasons, led the league in home runs in 1995 when the Cleveland Indians reached the World Series, and led the league in RBIs three times. In 1997, he hit free agency and became the first player in the history of the sport to receive a $10 million per year contract. In the winter before the 1999 season, he signed this massive contract with the Baltimore Orioles and immediately received great contributions from the Louisiana native before a chronic hip problem ended his career after just two seasons with the team.

5 Dan Uggla, 5 years, $62 million, 2011

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The Atlanta Braves once again make the cut as they provided one of the worst contracts in the history of Major League Baseball to the All Star second baseman, Dan Uggla. Uggla was coming off a career year in 2010 when he was about to become a free agent. The Braves decided to give Uggla this contract with the hopes that he would be able to repeat his .287 average with 33 home runs and 105 RBIs. In his first year with the Braves, he did hit a career-high 36 home runs, which was the fifth straight season he surpassed 30 home runs. Unfortunately for the Braves, that was the best the team got from him, as he hit a combined .209 with 79 home runs in 499 games before the team released him during the 2014 season and ate the rest of his contract.

4 Denny Neagle, 5 years, $51.5 million, 2000

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During the winter before the 2001 season, the Colorado Rockies decided to try and turn their fortunes around by bringing in solid pitching. They brought in Mike Hampton and Denny Neagle to anchor their rotation. Neagle had resurrected his career several years earlier with the Atlanta Braves when he won 20 games and finished third in the Cy Young race. With the Rockies, he never found his stride and played just three seasons with the team before retiring from the sport. When his time in Colorado was complete, he had compiled a 19-23 record with a 5.57 ERA.

3 Barry Zito, 7 years, $162 million, 2006

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Before the start of the 2007 season, the San Francisco Giants awarded Zito with this massive contract after he won 102 games with the Oakland Athletics. During his time with the Athletics, Zito won the American League Cy Young in 2002 after leading the league with 23 wins. It wasn’t until his third season with the Giants that Zito got his 23rd win with the club. While Zito did a fantastic job of staying healthy and pitching every fifth day, the performance he delivered wasn’t great. For some reason, the Giants decided to keep Zito throughout the length of his contract. Over that time, he was 63-80 with a 4.62 ERA.

2 Mo Vaughn, 6 years, $80 million, 1999

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During his time with the Boston Red Sox, Mo Vaughn was one of the most feared left-handed power hitters in the sport. He won the American League MVP award in 1995 and hit 230 home runs in eight seasons. He left the east coast and joined the Los Angeles Angels of Anaheim in 1999 and following the 2001 season that saw him play exactly zero games, traded him to the New York Mets. The Mets went on to give Vaughn this contract. While he hit 26 home runs in 139 games during his first season in New York, he would play just 27 games the following season before seeing his career end.

1 Mike Hampton, 8 years, $121 million, 2000

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The number one spot goes to the Colorado Rockies who signed left-hander Mike Hampton to this ridiculous contract before the 2001 season. Along with no.4 worst signing, Denny Neagle, the duo nearly destroyed this organization. Hampton spent two seasons with the Rockies, going just 21-28 with a 5.75 ERA before the team unloaded him and part of his hefty contract on the Atlanta Braves. When he joined the Braves, his play improved drastically and despite missing two full seasons due to injury, still found some success before officially retiring in 2010.

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