He has previously played in Major League Baseball (MLB) for the Chicago White Sox and Miami Marlins.

Anderson led the American League in batting average in 2019, won the Silver Slugger Award in 2020, and was an All-Star in 2021 and 2022.

Anderson played little league baseball as a kid but eventually cut the sport out of his life up until his junior year of high school.

[11] Returning to East Central for his sophomore year, Anderson had a breakout season, leading all junior college baseball players with a .495 batting average.

[11] He was named a first-team National Junior College Athletic Association Division II All-American.

[13] Though expected to make his professional debut with the Bristol White Sox of the Rookie-level Appalachian League,[12] the White Sox assigned Anderson to the Kannapolis Intimidators of the Single–A South Atlantic League instead, a higher level than rookie ball.

When he returned in August, the White Sox promoted him to the Birmingham Barons of the Double–A Southern League,[19] where he batted .364 in 10 games.

[20] The White Sox assigned Anderson to the Glendale Desert Dogs of the Arizona Fall League after the regular season.

[20] He spent the season with Birmingham,[22] batting .312 with five home runs and 49 stolen bases, while also committing 25 errors.

[23] Invited to spring training again in 2016,[24] the White Sox assigned him to the Charlotte Knights of the Triple–A International League at the beginning of the season.

[26] On June 10, 2016, the White Sox designated Jimmy Rollins for assignment and promoted Anderson to the major leagues.

[26] Anderson made his MLB debut that day, hitting a double off of Ian Kennedy of the Kansas City Royals in his first at bat.

[42] On July 10, 2021, Anderson was named to the 2021 MLB All-Star Game as a replacement for Carlos Correa, who had decided not to attend.

[49] Later in the game, White Sox catcher Yasmani Grandal confronted Donaldson, leading to both teams clearing their benches.

After the game, manager Tony La Russa called Donaldson's comment "racist" and Anderson agreed with him.

On July 30, 2022, Anderson was thrown out of the game by umpire Nick Mahrley after arguing balls and strikes.

MLB suspended Anderson for three games and fined him an undisclosed amount for making illegal contact with an umpire.

Anderson also went homerless until on July 29 against the Cleveland Guardians when he hit his first home run of the season and his first homer in 379 days off of Logan Allen.

[57] On September 3, Anderson notched his 1,000th career hit with a lead off double off of Detroit Tigers starter Tarik Skubal.

[71] Anderson has been known for doing charity work around the south and west sides of Chicago, which he calls his "adopted hometown".

In 2019, Anderson brought 75 kids from the south side of Chicago to the theater to watch the film 42 (2013), a biopic about baseball player Jackie Robinson.