Coming out of Jefferson Davis High School in Houston, Crawford was offered scholarships to play basketball as point guard at UCLA or to play football as an option quarterback at the University of Nebraska. Crawford turned down both offers in favor of a baseball career. He was drafted by the Devil Rays in the second round of the 1999 amateur draft (the 52nd overall pick). In 2002 the Tampa Bay chapter of the BBWAA named him the Devil Rays Most Outstanding Rookie and he earned International League Rookie of the Year playing for the AAA Durham Bulls.

Carl Crawford going back into the dugout.Crawford entered the major leagues at the young age of 20 and played in 62 games with the Devil Rays in his rookie 2002 season. In 2003, he played nearly every day, batting .281 with 54 runs batted in and led the league with 55 stolen bases. Along with Juan Pierre, Carl was co-winner of the Negro Leagues Baseball Museum James "Cool Papa" Bell Legacy Award for 2003.

In the 2004 season, Crawford stole 59 bases, again leading the league and posting the second-highest total in the majors that season, and hit .296 with 11 home runs and 55 RBIs. He was selected for the 2004 All Star Game, played in his hometown of Houston, and was named Devil Rays team MVP in 2004 by the BBWAA. Crawford led the league in triples in both 2004 (19) and 2005 (15).

Carl Crawford stated during February 2006 that his desire to be the number one fantasy baseball pick motivates him to train harder and work better, making him one of the first baseball players to openly talk about fantasy baseball as a motivation tool. For the 2007 Fantasy prospects, Crawford is the #2 outfielder on most boards. On Mother's Day, May 14, Crawford was one of more than 50 hitters who brandished a pink bat to benefit the Breast Cancer Foundation. On July 5, Crawford became only the eighth player in history to get 200 stolen bases before his 25th birthday. That same day, he also stole home plate for the first time in his career.