Crawford is a native of the Fifth Ward area of Houston. He participated in the Reviving Baseball in Inner Cities program, and attended Jefferson Davis High School in Houston, Texas, and was a letterman in football, basketball, and baseball. As a child, he was on the same little league team as Michael Bourn, who would become a star for the Houston Astros and the Atlanta Braves. In high school baseball, he began working with former #1 pick Willie Ansley after his sophomore year.He batted .638 as a senior. In the summer of his junior year in high school coach Ansley advised him to get on a team that played in the same tournaments that Josh Becket played in so he could be seen by the pro scouts and Crawford joined the Pasadena Stars select baseball team. It was there that he gained his first real exposure to Major League Baseball scouts. So intent on capitalizing on this exposure, he was advised by coach Ansley to skip basketball his senior year to concentrate on baseball so that his knees would be fresh from the beginning of the season. Crawford was offered scholarships to play basketball as a point guard at UCLA. He also had an option to play college football as an optionquarterback at Nebraska,USC, Oklahoma, Florida, and Tulsa. He had originally signed a letter of intent to play football for Nebraska but he turned down both offers in favor of a baseball career.
In 2004, Crawford stole 59 bases, again leading the league and posting the second-highest total in the majors that season. He batted .296 with 11 home runs and 55 RBIs. Crawford also hit a league-leading 19 triples. He was selected for the All Star Game, played in his hometown of Houston, and was named Devil Rays team MVP in 2004 by the BBWAA.
Crawford batted .301 in 2005, becoming just the third .300 hitter in Devil Rays history, joining Aubrey Huff (.311 in 2003) and Fred McGriff (.310 in 1999). Crawford also posted career highs in hits (194), home runs (15), and RBI (81). He again led the league with 15 triples and placed third in steals (46).
On July 5, 2006 against the Boston Red Sox, Crawford became only the eighth player in history to get 200 stolen bases before his 25th birthday. Crawford finished the season with career highs in batting average (.305) and home runs (18), joining Hall-of-FamerRogers Hornsby as the only players in Major League history to increase their batting average and home run totals every year for five straight years. He won a Fielding Bible Award for his defensive excellence in left field during the season.
Crawford was named an All-Star for the second time in 2007, becoming the first Devil Ray to receive the honor more than once. He homered in the 6th inning of the All-Star Game, on a 3–2 pitch from Francisco Cordero of the Milwaukee Brewers.
In the second half of the season, Crawford had a sore right wrist which had been bothering him for some time, and did not hit a home run for a period of 42 days. Prior to a game against the Toronto Blue Jays, he had an MRI and was listed as doubtful to play because of the wrist. However, he pinch hit as the game went into extra innings and hit a walk-off home run, ending his drought. This kicked off a run of four homers in ten games. In August, ESPN.com named Crawford the Devil Rays' "Face of the Franchise".
On April 11, 2008, Crawford accumulated his 1,000th hit, making him the eighth player to hit 1,000 and steal 250 bases before turning 27. In game four of the American League Championship Series against the Boston Red Sox, Crawford tied an ALCS record with five hits in one game, going 5–5 and stealing two bases. After the season, he won his second Fielding Bible Award.
In 2008, he had surgery to fix the tendon of the middle finger of his right hand.
On May 3, 2009, Carl Crawford tied a modern-era record by stealing six bases in a game against the Boston Red Sox, part of a team-record eight total stolen bases. On July 14, 2009, Crawford represented Tampa Bay in the 2009 All Star Game, where he was named MVP for a leaping catch at the top of the 8-foot outfield wall to prevent a possible go-ahead home run by Rockies outfielder Brad Hawpe.
In 2009 he had the best range factor of all starting major league left fielders (2.34). He won his second consecutive Fielding Bible Award and third overall at left field.
On July 31, 2010, Crawford reached 400 stolen bases. He is the 7th player in history to reach that mark before his 29th birthday.
On August 17, 2010, Crawford hit the 100th triple of his career, joining Ty Cobb as the only major league players to hit 100 triples and steal 400 bases before the age of 30.
On December 8, 2010, Crawford signed a 7-year, $142-million contract with the Boston Red Sox. Crawford struggled to begin the 2011 season, batting .137 and stealing only 2 bases in his first 12 games. On May 3, he hit his 1,500th career hit, a single against Dan Haren of the Los Angeles Angels in the 3rd inning, becoming the 588th player with 1,500 or more career hits.
For the 2011 season, he batted .255 with an on-base percentage of .289. Through 2011, he had the third-best career fielding percentage (.990) among all active major league left fielders, behind Ryan Braun and Reed Johnson.
Crawford injured his left wrist in January 2012. He had wrist surgery to repair cartilage damage, but had discomfort in his elbow and was told he had a sprained ligament.
He began the 2012 season on the 60-day disabled list. He had a rehab assignment with the Gulf Coast League, Double-A Portland, and Triple-A Pawtucket to recover from both injuries.
Crawford made his 2012 regular season debut on July 16, 2012, against the Chicago White Sox, and batted 2nd.
After being traded to the Dodgers, Crawford voiced his unhappiness with the Red Sox organization and the city of the Boston, claiming that the baseball environment was "toxic" and that he was in a "depression stage" with Boston.