7 MLB Contracts That Became Nightmares

With free agents cashing in big this off-season, it’s wise for teams to revisit some of the horrible contracts of the past. From extensions for franchise players to ill-advised free agent deals, there have been countless misfires by Major League Baseball general managers and owners in recent years. Here are seven contracts that quickly turned into nightmares for the teams in question.

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Source: White House / Pete Souza

7. Ryan Howard, Philadelphia Phillies

Though critics were horrified by the deal, Ryan Howard was all smiles when the Phillies offered him a five-year contract extension worth $125 million. Instead of waiting until the end of his contract, which expired after 2011, the Phillies locked up their aging slugger early in 2010.

This move became a case of how not to manage a franchise’s money. Age and injury caught up with Howard quickly, making the deal a major black eye for Phillies GM Ruben Amaro. Philadelphia still owes Howard $25 million per year through 2016 for what is likely going to be average production.