Hughes has played for the Philadelphia 76ers, Golden State Warriors, Washington Wizards, Cleveland Cavaliers, Chicago Bulls, New York Knicks, Sacramento Kings, Charlotte Bobcats, and Orlando Magic. He was drafted by Philadelphia in the 1st round of the 1998 NBA Draft out of Saint Louis University, where he was named Freshman of the Year. He is known for being a versatile and athletic guard with strong defensive abilities, and was selected to the 2004–05 NBA All-Defensive 1st Team as a member of the Wizards. He led the league in steals per game with 2.89 in 2004–05.

Hughes started his basketball career at Christian Brothers College High School, winning the Missouri state championship in 1997. Hughes played 1 season of college basketball at Saint Louis University.

He finished the 1997–98 season with per game averages of
+ 20.9 points,
+ 5.1 rebounds,
+ 2.4 assists,
+ and 2.16 steals.

He led the Billikens to the NCAA Tournament that year, making it to the second round after a win over University of Massachusetts.