By the time Rose enrolled at Simeon Career Academy in 2003, he was a hot commodity for collegiate coaches. Despite his reputation, he played freshmen and JV basketball for the Wolverines. He wore No. 25 in honor of Ben "Benji" Wilson, a promising player who was murdered by a gang member during his senior year in 1984. Rose was not allowed on varsity due to a long-standing tradition that head coach Bob Hambric, who had been with the school since 1980 had no freshmen on the varsity team. That rule did not lessen Rose's play, and he went on to put up 18. 5 points, 6. 6 assists, 4. 7 rebounds and 2. 1 steals per game and led both the freshmen and sophomores to city championships with a 24–1 record. Hambric softened his stance and allowed the freshman a chance to play on varsity in the state tournament, but Rose declined, wanting the players to get due credit. The next year Hambric retired and Robert Smith was hired, opening the path to varsity. In Rose's debut, he had 22 points, 7 rebounds and 5 steals over Thornwood High School in a sold-out game filled with college scouts and coaches. He led the Wolverines to a 30–5 mark while averaging 19. 8 points, 5. 1 rebounds, 8. 3 assists and 2. 4 steals but the season ended after a loss in state regionals. Rose's play garnered him his first national award: a Parade All-American third team spot.
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