Worst Recent Contracts for the New York Yankees

The Derek Jeter era will officially come to an end next May after his number No. 2 is retired. The high point of the New York Yankees most recent dynasty run was winning four World Series titles in five seasons. However, it has been a few years since a victory parade has overtaken the Canyon of Heroes in Mid-town Manhattan.
In the 13 seasons following the dynasty run, the Yankees have hoisted the World Series trophy only once as team management chose to rebuild the roster through free agency and the results have been anything but ordinary. Yes, the Yankees had their share of buyer’s remorse; some of the free agent signings have blossomed into good investments, while others haven’t reached that pinnacle. Free agency isn’t an exact science as teams are paying big money for players in their declining years.

P Kei Igawa

The signing of Kei Igawa is still the most baffling free agent signing in the history of baseball. The Yankees gave $46 million to a pitcher that had a below average fastball and questionable control. Thankfully, the Igawa experiment only lasted for 16 major league appearances before the Yankees realized he was fraud. Igawa’s relationship with the franchise quickly deteriorated after he refused a minor league assignment to the club’s Triple A team. Only after a lengthily negotiation did Igawa agree to a demotion to Double A Trenton because it allowed him to travel from his Manhattan apartment to home games.

P Carl Pavano

Following the 2004 season, Florida Marlins starting pitcher Carl Pavano became the prized free agent target of the offseason. Pavano had a dominant year by going 18-8 with a 3.00 ERA. Many of the contenders were in on the chase, but in the end, the Yankees outbid their opponents. Halfway through his first season in New York, Pavano develop shoulder and rotator cuff tendonitis that effectively ended his year. Next spring training; Pavano needed surgery to remove bone chips in his elbow after he altered his delivery due to a back injury. During rehabilitation, Pavano was involved in an automobile accident that broke a rib, which made it impossible for him to pitch. Somehow, Pavano pitched well enough in spring training to become the Yankees opening day starter in 2007, but his season abruptly ended after tearing an elbow tendon that required Tommy John surgery. This injury was the final straw in Pavano’s unproductive career in New York that lasted only 26 starts over four seasons.

P A.J. Burnett

The Yankees qualified for the postseason every year from 1995-2007, as they claimed six American League pennants and four World Series titles. However, when the club missed the playoffs in 2008, the Steinbrenner family decided to go all in on signing free agents. In came CC Sabathia and Mark Teixeira, but the head-scratching move was the signing of hard-throwing starting pitcher A.J. Burnett to a five-year/$82.5 million deal. His first season in New York was memorable; Burnett had a respectable 13-9 record with a 4.04 ERA and played a key role in the 2009 World Series team. The next two seasons were anything but memorable as Burnett had trouble keeping the ball in the park. His record was a disappointing 21-26 with a 5,20 ERA. Suddenly, Burnett was a liability in the starting rotation. Prior to the start of the 2012 season, the Yankees traded him to the Pittsburgh Pirates for two low-level minor leaguers. Plus, the team agreed to pay $18 million of the $31 million remaining on the contract.

P Jose Contreras

Back in 2002, the Yankees thought Cuban sensation Jose Contreras was the logical successor to fellow Cuban Orlando “El Duque” Hernandez in their starting rotation. However, once Contreras made his way onto the mound, it was apparent that he had little in common with Hernandez. Contreras struggled badly and posted a 5.64 ERA in 18 starts, and which forced the Yankees to deal him in a 2004 deadline trade with the Chicago White Sox. To get the deal completed, the Yankees guaranteed they would play Contreras’ salary for the remainder of the contract.

OF Jacoby Ellsbury

Jacoby Ellsbury is in the midst of a seven-year/$153 million deal as his best statistical season was his first (.271, 16 HRs and 71 runs scored) in pinstripes. Ellsbury’s next two seasons have been filled with multiple disabled list stints for a variety of injuries that limited his production at the plate. Clearly, the Yankees thought they were signing one of the premier leadoff hitters in baseball, who has great speed and excellent defensive skills. Ellsbury hasn’t been the same player that tormented the Yankees during his time with the Boston Red Sox.

Michael Morris
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