After a college career at Georgia Tech, he played point guard professionally from 1991 to 2006, mostly in the National Basketball Association.

[1][2] Collegiate recruiters began scouting Anderson in sixth grade and he was on the front page of the New York City sports section when he was 14.

[3] By the end of his high school career, he was a four-time Parade All-American, a feat not accomplished since Lew Alcindor, and the first player to be named All-City four times.

This record stood until 2004, when Lincoln High School guard Sebastian Telfair eclipsed the mark late in his senior season.

After a long recruiting process, Anderson signed a letter of intent in November 1988 to play at Georgia Tech, selecting the Yellow Jackets over North Carolina, Duke, and Syracuse.

During Anderson's second season he nearly doubled his point, rebound, and assist averages en route to the Nets making the 1993 NBA playoffs.

While in New Jersey, coached by Chuck Daly, Anderson formed what was widely expected to become a "big three" of sorts with Derrick Coleman and Dražen Petrović.

[9] That season, on February 18, 1994, Anderson scored a career-high 42 points and recorded 14 assists during a 119–114 win over the Detroit Pistons.

During the 1997 NBA playoffs, Anderson averaged 17 points, 4.8 assists, and 4.3 rebounds per game during Portland's first-round loss to the Los Angeles Lakers.

[14] In 1998, the Trail Blazers traded Anderson, along with Alvin Williams, Gary Trent, and two 1998 first-round picks to the Toronto Raptors for Damon Stoudamire, Carlos Rogers, Walt Williams, and a 1998 second-round pick, but he refused to report to the team because he did not want to play in Canada, which prompted the Raptors to trade him to the Boston Celtics five days later, along with Žan Tabak and Popeye Jones for John Thomas, Roy Rogers, Chauncey Billups, and Dee Brown.

In 2003, Anderson was traded to the Seattle SuperSonics, along with Vitaly Potapenko and Joseph Forte, and in a package for Vin Baker and Shammond Williams.

At the 2003 NBA trade deadline, Anderson was dealt back to the Hornets, who had since relocated to New Orleans, for Elden Campbell.

[15] His play was instrumental for the United States and included 34 points performance in their 107–105 comeback overtime win against Puerto Rico in the bronze medal game.

For his effort he was named to the All-Tournament Team which included Vlade Divac, Toni Kukoč, Oscar Schmidt and Fico Lopez.

[27][28] In August 2011, Anderson took the position of basketball coach at the David Posnack Jewish Day School in Davie, Florida.