Henderson played two years of college soccer at UCLA, where he helped the team win a national championship his sophomore season.

He immediately stood out by starting 29 games, scoring three goals and eight assists, and being named the Rapids' team MVP.

Henderson was even better in 2000, scoring nine goals and nine assists as one of the major players in the Wizards team that won the MLS Cup.

He moved to the Miami Fusion for the 2001 season, where he scored three goals and eight assists on a team that went on to win the MLS Supporters' Shield in their final year.

[3] He started in a victory over Iceland and quickly established himself on the national team, seeing time in nearly every game leading up to the 1990 FIFA World Cup.

His last game in the 1990s came in a February 25, 1998 loss to Belgium as the U.S. prepared for the 1998 FIFA World Cup Henderson did not earn his next cap until October 25, 2000.

On January 24, 2008, it was announced that Henderson would be joining the front office of the Seattle Sounders FC as the technical director.

[5] Henderson was named the chief soccer officer and sporting director of Inter Miami CF on January 18, 2021.