Coco Crisp was originally drafted by the St. Louis Cardinals in 1999. On August 7, 2002, while playing at AA-level New Haven, Crisp was traded to Cleveland to complete an earlier trade for pitcher Chuck Finley.
Crisp became the starting center fielder with the Indians in mid-2002, replacing Milton Bradley. For the next few seasons, Crisp established a reputation as an excellent fielder and speedy baserunner. Despite his success, Crisp had to fight for his roster spot each spring. In 2005, Crisp moved to left field following the emergence of another young outfielder, Grady Sizemore. In his final two seasons with the Indians, Crisp showcased his offensive talent by batting .297 and .300 with 31 total home runs and 35 steals.
Crisp began the 2007 season struggling offensively. On April 20, 2007, Crisp fell over a short wall at Fenway Park while trying to catch a home run by Alex Rodriguez. Although he was unable to make the catch, missing by inches, he hit a game tying triple off of Mariano Rivera in the bottom of the eighth. The Red Sox went on to win 7-6. During this season he has made numerous impressive catches in the outfield. It has even been claimed by one major league club that Crisp is easily the best defensive center fielder in all of Major League Baseball.