Born in Morgantown, West Virginia, Henderson attended Brebeuf Jesuit Preparatory School in Indianapolis, Indiana.

They lost the state championship game his senior year to Glenn Robinson's Gary Roosevelt squad.

He remained a member of an Atlanta team that for nine of his tenured seasons did not improve significantly nor get very far in the postseason when they qualified for the Playoffs.

On August 4, 2004, along with Jason Terry, Henderson was traded to the Dallas Mavericks for Antoine Walker and Tony Delk.

On September 17, 2005, Henderson signed with the Cleveland Cavaliers, appearing in 51 games as a reserve power forward.