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Alex Rodriguez
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Alex Rodriguez, aka A-Rod, is synonymous with the New York Yankees' dominance in the late "aughts," including a World Series title in 2009. But before he played in pinstripes, he was a hotshot shortstop coming off some impressive All-Star seasons with the Seattle Mariners. The year was 2001 and the Texas Rangers were looking for a marquee player to lead them to the World Series, or at least the American League playoffs, a level of postseason play they hadn't reached in franchise history. They believed that savior was A-Rod.

Apparently, it's good to be the savior. Texas offered Rodriguez the highest paying contract in baseball history, a bank-busting $252 million over ten years. The contract, unfortunately, was cursed from the start. No matter how well A-Rod performed in Texas, he would never outlive the enormous folly of those $252 million. He belted in 52, 57 and 47 homeruns in the three years he played for Texas and always had a .300-plus batting average. Of course, it would come out later that he was using steroids during this period, but A-Rod cited the pressure of living up to his absurdly big paycheck.

Even with A-Rod's solid (albeit juiced-up) performance and the Rangers' all-in investment in him, none of it changed the team's fate. The Rangers never did made it to the playoffs (not until 2010, at least), and when the team recently filed for bankruptcy as part of a sale to ex-Rangers star Nolan Ryan, the largest creditor still on the books was one Alex Rodriguez, for $24.9 million [source: Morath].

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