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Carey played for the Pirates from his arrival in the league in 1910 until 1926, winning a World Series championship in 1925. He was known as a skilled fielder and excellent base stealer. He regularly stole 40 or more bases and maintained a favorable steal percentage; in 1922 he stole 51 bases and was caught only twice. He also stole home 33 times in his career, second best only to Ty Cobb's 50 on the all-time list.