Ankiel was a pitcher with the Cardinals from 1999 until 2001, when he lost his ability to throw strikes consistently. After trying to regain his pitching form in the minor leagues and briefly returning to the majors in 2004, he switched to the outfield in early 2005. For two and a half years, he honed his skills as a hitter and fielder in the Cardinals' minor-league system. He returned to the Cardinals on August 9, 2007. As a Cardinal until 2009, Ankiel hit 47 home runs as an outfielder and two as a pitcher. After the 2009 season, Ankiel became a free agent. Subsequently, he was signed by the Royals and later was traded to the Braves.

Ankiel became the first player since Babe Ruth to have won at least 10 games as a pitcher and also hit at least 50 home runs. Ankiel is also the only player other than Ruth to both start a postseason game as a pitcher and hit a home run in the postseason as a position player. His change of position, and the fact that he played for six teams in a five-season span, suggest that Ankiel's playing history represents "one of the stranger careers in baseball history" in the words of journalist Barry Petchesky.

Ankiel attended Port St. Lucie High School in Florida, where he went 11–1 with a 0.47 earned run average (ERA) during his senior season, striking out 162 batters in 74 innings pitched, and was named the High School Player of the Year by USA Today in 1997.

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