[4] In NBA history, Crawford ranks 29th with four 50+ point games accrued (tied with 9 others, including George Mikan and Larry Bird)[5] and 12th all-time in career three-point field goals made (2,221).

Growing up in South Seattle, Crawford played for Rainier Beach High, a school that has produced a number of other NBA and college players such as Doug Christie, Nate Robinson, Terrence Williams, Kevin Porter Jr., and Dejounte Murray.

In 2001, Rainier Beach retired his number 23 jersey to commemorate his impact;[9] and in 2018, it inducted him into its Hall of Fame to honor his legacy.

[10] Having earned a scholarship to the University of Michigan, Crawford committed to play college basketball with the Wolverines under coach Brian Ellerbe.

At the start of the 1999–00 season, however, he incurred a six-game suspension from the National Collegiate Athletic Association (NCAA);[11] it retroactively ruled that his high school living arrangement had breached its bylaws on amateurism.

[12] Crawford was selected 8th overall in the 2000 NBA draft by the Cleveland Cavaliers but was then traded to the Chicago Bulls in a draft-day deal that included the rights to Chris Mihm.

In his first year with the franchise, the 2004–05 season, he played 70 games (67 starting) and averaged 17.7 points, 2.9 rebounds, 4.3 assists, and 1.4 steals per contest.

[19] In his second year in New York City, the 2005–06 season, he took a reduced sixth man role under head coach Larry Brown.

[22] Crawford was limited to 59 games (36 starting) due to an ACL injury;[23] but he averaged 17.6 points, 3.2 rebounds, and 4.4 assists on the season.

[25] Crawford provided the 23–59 Knicks with one of the few bright spots on January 26, 2007: He scored a career-high 52 points, with 16 of his shots being made consecutively and 8 of his three-pointers being one short of the franchise record set in 2002 by Latrell Sprewell.

[27] Crawford proved an ideal fit in the run-and-gun offense of coach Don Nelson due to his three-point shooting and ball-handling ability as well as court-vision.

[29] At the end of the season, the Atlanta Hawks acquired Crawford in a trade for guards Acie Law and Speedy Claxton.

[31] In a win over the Los Angeles Clippers on February 3, 2010, Crawford set an all-time NBA record for most career four-point plays, surpassing Reggie Miller.

[32] Backing up All-Star guard Joe Johnson and Mike Bibby, he averaged 18 points, 2.5 rebounds, and 2 assists off the bench.

[38] He averaged nearly 14 points in 60 games while leading the league in free throw percentage with a career-high 92.7 percent in the lockout-shortened season.

[7] In the 2013–14 season, Crawford led the league's reserve players in scoring with 18.6 points per contest to go along with 3.2 assists and 2.3 rebounds.

[45] On April 8, 2016, he made a three-pointer with 0.2 seconds left and finished with 30 points in the Clippers' 102–99 overtime victory over the Utah Jazz.

He joined Ray Allen, Reggie Miller, Jason Terry, Vince Carter and Paul Pierce in the 2000 club.

[52] On July 6, 2017, the Clippers traded Crawford and a 2018 first-round pick to the Atlanta Hawks as part of a salary dump that cleared the way to acquire Danilo Gallinari from the Denver Nuggets by a sign-and-trade deal.

[56] Two days later, he scored all 17 of his points in the fourth quarter and made a 3-pointer with 27.5 seconds left to help the Timberwolves hold off the Utah Jazz 100–97 in their home-opener.

[57] During a 108–107 victory over the Portland Trail Blazers on December 18, 2017, Crawford made a season-high 23 points in only 23 minutes, with 16 of them scored in the fourth quarter.

[70] His one appearance for the Nets was ultimately his final NBA game, as Crawford did not play for any team during the 2020–21 or 2021–22 seasons, as he officially announced his retirement from the league on March 21, 2022.

[71] Crawford started doing game broadcasts for NBA League Pass alongside Quentin Richardson in November 2021.

[72] Crawford has signed with MSG Network's coverage of the New York Knicks starting with the 2024–25 NBA season to fill-in for about ten games as backup color analyst on television.

[74] A staple of the Seattle basketball community, Crawford has organized secret workouts around the city, recruiting a revolving cast of elite-level participants that include the likes of Zach LaVine and Kyrie Irving.

Among other charitable community activities, Crawford provides a platform for local players aspiring to progress from amateur status to professional through "The Crawsover" league.