Crawford played 19 big league seasons, starting his career in 1899 with the Cincinnati Reds, before jumping to the newly founded American League's Detroit Tigers in 1903, where he finished out his career.
Crawford twice led the major leagues in home runs, hitting 16 in 1901 and 7 in 1908. He still maintains the major league record for the most inside-the-park home runs in a season with 12 in 1901, and the most in a career with 51.
Crawford also holds the career major league record for triples with 309, a record unlikely to be beaten given the difference in the style of baseball played in the modern era compared to that of the dead-ball era of Crawford. When he retired, he had a career batting average of .309. Crawford fell just short of the magical 3000 hit club, compiling 2961. There has been debate about whether Wahoo Sam, as he was called, deserves inclusion in the 3,000 hit club. Crawford maintained that the 87 hits he got in the Western League, which became the American League in 1900, were supposed to be included in his official total under the 1903 agreement between the two leagues.
He played twelve years in the same outfield with Ty Cobb, accompanying him to the 1907, 1908, and 1909 World Series, falling to Honus Wagner's Pittsburgh Pirates in 1909 in seven games.
Crawford was selected by the Hall of Fame Veterans' Committee to join the Hall with the Class of 1957.