The Chicago White Sox selected Anderson in the first round, with the 17th overall selection, in the 2013 MLB Draft. Anderson opted to sign with the White Sox, rather than enroll at UAB, for a signing bonus of $2,164,000. Though expected to make his professional debut with the Bristol White Sox of the Rookie-levelAppalachian League, the White Sox chose to assign Anderson to the Kannapolis Intimidators of the Class ASouth Atlantic League instead, where he batted.277/.348/.363. In 2014, Anderson began the season with the Winston-Salem Dash of the Class A-AdvancedCarolina League. He broke his wrist in late June, requiring surgery. In 68 games, Anderson had a.297 batting average, six home runs, 10 stolen bases, and 31 errors. When he returned in August, the White Sox promoted him to the Birmingham Barons of the Class AASouthern League, where he batted.364 in 10 games. The White Sox assigned Anderson to the Glendale Desert Dogs of the Arizona Fall League after the regular season. The White Sox invited Anderson to spring training in 2015. He spent the season with Birmingham, and he batted.312 with five home runs and 49 stolen bases, while on defense he committed 25 errors. Invited to spring training again in 2016, the White Sox assigned him to the Charlotte Knights of the Class AAAInternational Leagueat the beginning of the season. In 55 games for Charlotte, Anderson batted.304 with four home runs, 20 RBIs, and 11 stolen bases. On June 10, 2016, the White Sox designatedJimmy Rollins for assignment and promoted Anderson to the major leagues. Anderson batted.283 with nine home runs in 99 games for the White Sox. Before the 2017 season, Anderson signed a six-year contract worth $25 million, with two club options for the 2023 and 2024 seasons. In 2017 he batted.257/.276/.402, walked in 2.1% of his at bats, and had the lowest walks-per-strikeout ratio in the majors. On defense, he led the major leagues in errors, with 28, and in fielding errors and throwing errors. In 2018 he batted.240/.281/.406. On defense, he tied for the major leaguelead in throwing errors, with 12. In 2019 he batted.335 /.357/.508. He had the lowest walk percentage in the American League. He had career highs in hits with 167, despite having 88 less plate appearances than in 2018. He also had a career high in doubles with 32, and runs with 81. On defense, he led all major league players in errors committed, with 26, and had the lowest fielding percentage of all major league shortstops.