on november 20, 2013, the padres traded anna to the new york yankees for ben paullus. in spring training in 2014, anna competed with eduardo núñez, zelous wheeler, yangervis solarte, and scott sizemore for a reserve infielder role with the yankees. anna ultimately won a spot on the yankees' opening day roster. anna hit his first career home run on april 10, against boston red sox pitcher clay buchholz.