Bailey was selected by the Florida Marlins in the 2nd round (64th overall) of the 1997 draft. Bailey began his professional career in 1997 playing for the Gulf Coast League Marlins and played in the Marlins minor league system until 2001.\n', '

In March 2002 the Marlins traded him to Montreal Expos for a player to be named later (Wilson Valdéz). He played in the Expos system until October 2003 when he granted his free agency.\n', '

Bailey was signed as a free agent by the Red Sox organization first on November 7, 2003, then again on December 15, 2004, December 10, 2006 and December 13, 2007.\n', '

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