In 1996, Anderson helped the University of Kentucky win the NCAA Men's Basketball Championship as part of a team that featured nine future NBA players under their coach Rick Pitino.

Despite missing much of his senior season at Kentucky due to a torn anterior cruciate ligament (ACL), Anderson was selected by the Cleveland Cavaliers with the 13th overall pick in to the 1997 NBA Draft.

In his debut game on October 31, 1997, Anderson recorded 6 points, 3 rebounds, 1 block and 1 steal as the Cavaliers fell short to the Houston Rockets 86 - 94.

He was the starting shooting guard for the Spurs that entire 2000 - 2001 season and averaged 15.5 points, 4.4 rebounds, and 3.7 assists in 34.9 minutes per game.

On August 3, 2005, he was the first player in the league waived using the so-called "luxury tax amnesty clause" of the 2005 NBA collective bargaining agreement.

After playing 20 games for the Rockets (averaging 13.4 points, 5.1 rebounds and 3.3 assists with the team) he was traded to the Miami Heat in exchange for Gerald Fitch on February 23, 2006.

The foundation provides programs focused on education, mentorship, and wellness, helping young people build the resilience and skills they need to succeed.