1. Johnny Damon
In his eighth season in the Majors, Damon joined the Red Sox via free agency. Damon may have only played five seasons with the Red Sox, but he quickly became a fan favorite. His name will forever be enshrined in Red Sox history as he was one of the main contributors to the Red Sox’ 2004 World Series title that broke the “Curse of the Bambino.”
Despite the fact that Damon was beloved in Boston and helped them win that elusive World Series title, he became an evil foe of Red Sox Nation when he made the decision to sign with the Yankees after the 2005 season. Unlike Ellsbury, Damon continued to thrive after he joined the Yankees. In 2009, Damon batted .285 and compiled twenty-four home runs. His biggest contribution as a Yankee came later that year. Damon completed the magical double-steal in the World Series against the Phillies after they failed to cover third-base.
Damon sits at the #1 position because he contributed to a World Series title for both the Red Sox and the Yankees, an amazing feat really.