Head attended Chicago\'s Manley Academy where he averaged over 20 points, eight assists and seven rebounds per game as a junior. Those numbers earned him All-City honors and he was selected MVP of the Blue Division of the Chicago Public League. Led by Head and head coach Bo Delaney, Manley had a perfect 12–0 record and won the conference championship in the Blue-West Division. Manley finished 26–7 overall, losing to state runner-up Chicago Westinghouse in the Public League quarterfinals. During the season, Head posted 10 triple-doubles. In a game against Chicago Wells, Head broke the city record and recorded the second-highest number of assists in a game with 25, earning Prep Player of the Week honors from the Chicago Tribune. That game also earned him Gatorade Prep Player of the Week honors. During the IHSA State Playoffs, Head scored 26 points and contributed 15 assists against Marshall in a first-round playoff victory. He would then post a triple-double in a second-round win over Steinmetz. During the summer, Head attended the Adidas ABCD Camp in New Jersey.\n', '

As a senior, Head averaged 22 points, eight rebounds, six assists and five steals in the rugged Red-West Division of the Chicago Public League. He would earn First-Team All-State honors in 2001 from the Chicago Tribune, Chicago Sun-Times, Champaign-Urbana News-Gazette, Associated Press and Illinois Basketball Coaches Association. Head was also selected to play in the Wendy\'s All-Star Classic as a senior. He played primarily point guard in high school but occasionally played shooting guard to complement his abilities. Head also finished sixth in the voting for Mr. Basketball in the state of Illinois following his senior year. However, to many college scouts, Head\'s senior year was seen as a disappointment as a few of his statistics dropped since junior year. Nevertheless, he would sign his letter of intent to play college basketball for the University of Illinois where he became the first Illinois recruit from the Chicago Public League since 1994.\n', '

As a freshman at the University of Illinois, Head saw limited playing time. Coach Bill Self had a veteran team which included Brian Cook and Frankie Williams, so he had little need to play a freshman. His playing time increased as the season progressed and he started 13 games, including 11 of the last 12. Head averaged 4.5 points in 16.6 minutes per game for the season while shooting 51 percent from the field (63-of-124). His first season showed Head\'s individual talent for shooting and defense as he was second on the team with 34 steals. He showed his potential to become an eventual offensive force when he scored a season-high 19 points in an NCAA Tournament first-round win over San Diego State, hitting 8-of-11 shots, including three three-pointers. In that same game, he tallied four assists and three steals against the Aztecs. His season-high for assists was six against Kansas in the Regional Semifinal game which proved that he could perform on the national stage against even the best teams in the nation.\n', '

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