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The 5 Worst Contracts In Tri-State Area Baseball History

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Over the last few weeks, we here at Double G Sports have been listing some of the worst contracts in tri-state area sports history. We have covered three of the major sports up to this point and to be frank, there have been some awful deals mentioned especially in basketball (thanks New York Knicks).


In the final installment, we will feature America’s Pastime. In the history of tri-state area baseball, bad contracts were the norm in the 1990’s and the early 2000’s. Both the New York Yankees and the New York Mets were, let’s say, very generous to players in order to get them to their teams and play in the mecca of sports. Needless to say mistakes were made and some (the Mets) are still paying for their sins to this day. Let’s start with number five.


  1. Johan Santana- 6 years/$137.5 million in 2008


The Johan Santana deal was bad but at the moment, it was needed for the Mets. A two-time Cy Young award winner, Santana was probably the best pitcher in baseball at the time. A 16-7 record in the first season of the contract had many believing that the Mets made the right move and that Santana may be leading the team to the playoffs and maybe even beyond.


While Met fans had dreams of the World Series, Santana began to break down in 2009 as he began dealing with arm issues. In 2010, he underwent surgery to repair a torn anterior capsule in his left shoulder and he missed the entire 2011 season. His career was never the same after that, although he was able to gut out 134 pitches to pitch the first ever New York Mets no-hitter on June 1, 2012. After that Santana re-tore the capsule in his shoulder and the Mets bough out the remainder of his contract in 2013. When it comes to Santana, it’s always going to be the story of what if.


  1. Jason Bay- 4 years/$66 million in 2010


A player always comes along that always seems to succeed when they are playing in a small market or on a team with stars hiding them from the public. Jason Bay was that player as he hit 184 home runs in eight seasons with the Pirates and the Red Sox before signing with the Mets in 2010.


While the contract was for four years, Bay only lasted three years in New York as he was just a disaster with the Mets. Bay only hit .234 with just 26 home runs in 288 games as a member of the Mets (to put that in perspective, he hit 36 home runs in 151 games a season prior with Boston). The fans became impatient as he was constantly serenaded with boos every time he was in left field at Citi Field and it just got worse and worse for him. His final season in New York saw Bay hit an embarrassing .165 in 2012 and after the season, the Mets released Bay from his contract and Bay’s career ended just a season later.


  1. Carl Pavano- 4 years/$39.5 million in 2004


Carl Pavano was never a great Major League Baseball pitcher for most of his career. With a 57-58 career record and an ERA of about 4.00, many would believe that Pavano would never be in line for a big money contract at any point in his career. However Pavano experienced a major abnormality in his career in 2004 when he won 18 games and pitched his way to a 3.00 ERA for the Florida Marlins. That one year proved to be Pavano’s best year of his career and the Yankees jumped all over him to sign him to a contract that would pay him almost $10 million a year.


Pavano’s Yankee tenure was derailed by injuries every season he was in New York. His first three months in pinstripes in 2005 were great with seven quality starts early in the season before shoulder issues kicked in. Pavano then injured his buttocks (yup, his buttocks) during Spring Training the following year and then he was injured in a car accident as the 2006 season saw Pavano not pitch one inning of baseball in the majors. Teammates began to question his desire to pitch and compete and it was all over from there.


Here are Pavano’s number from his three years of being a New York Yankee: 9-8, 5.00 ERA and 26 games pitched. That’s all I have to say about that.


  1. Alex Rodriguez- 10 years/$275 million in 2007


The A-Rod deal was controversial from the start. There were numerous reports after the deal was announced that Yankees general manager Brian Cashman did not want the deal but Yankee brass pushed for the deal. This is after Rodriguez opted out of his original 10 yr./$252 million deal with the Texas Rangers which he bought along with him to the Yankees. The new deal also included bonuses for home run milestones all the way up to Barry Bonds’ record number of 762 home runs.


The deal became a terrible idea after A-Rod first admitted to taking performance enhancing drugs in 2009 and his credibility began to disappear. There were reports that Rodriguez also took PED’s from a doctor in Canada but that was never proven. It all hit the fan in 2013 as Rodriguez was named as one of the players who received and took PED’s from the Biogenesis lab in Miami from Anthony Bosch. He was eventually suspended for the entire 2014 MLB season and his legacy was forever tarnished.


On the field, his performance dropped off significantly since signing his new contact. His batting average has dropped in the last three seasons and while he contributed to the Yankees 2009 World Series championship, Yankee fans were beginning to get aggravated with A-Rod’s lack of clutch hits when the team needed it. At this stage and after his suspension, the Yankees would be better off to just cut him but then they would still owe Rodriguez millions of dollars since that money is not insured due to Rodriguez’s numerous injuries. Needless to say, the Yankees are stuck with Alex Rodriguez for the foreseeable future.


  1. Bobby Bonilla- 5 years/$29 million in 1992

This is the mother of all bad contracts. Becoming the highest paid player in baseball at the time, Bonilla was a good player for a Pittsburgh Pirates team that featured Barry Bonds and Andy Van Slyke in the lineup. While having protection around him, Bonilla hit .284 in six seasons with the Pirates winning three Silver Slugger awards and making four All-Star teams.


Bonilla was not in a stacked lineup upon his arrival in Flushing with names like Darryl Boston and Chico Walker in the lineup regularly. He was an average hitter during his first go around with the Metropolitans but he did hit for power which some fans took solace in. However Bobby fought with teammates and the New York press constantly and just became an unbearable word that I will not write. Those mid-90’s Mets teams were horrendous as the team showed no signs of life with terrible front office moves and even worst managing so all the blame can’t go on Bonilla…but he definitely contributed a lot to the disaster. Bonilla was eventually traded in 1995 but he was traded back to the Mets in 1999.


His second stint with the team was marred with disagreements with manager Bobby Valentine about playing time and him paying cards with Rickey Henderson during a playoff game. The Mets finally wanted to cut ties with Bonilla but they still owed him money. Both sides came to a middle ground…the Mets would not pay him for 10 years and begin paying Bonilla $1.1 million a year from 2011 until 2035. So the Mets are still paying money to this day for a career .279 hitter. Ladies and gentlemen, the New York Mets.

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Kahlil Thomas

Kahlil is the College Sports Editor for as well as a columnist, hosting the Bump 'N Run column once per week. He also co-hosts a weekly basketball podcast, The Box Out, every Thursday evening with fellow writer Jason Cordner.
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