Holloway was considered one of the top point guard prospects in his high school class playing for St. Patrick, with some of the scouting reports naming him as the best point guard in the nation. He and Mike Bibby were consistently named as the two best point guards of the 1996 class. Selected 3 times in the All-State selection, In 1995 he was amongst the top scorers of the Reebok Big Time Tournament with an average of 26. 3 points per game, and he was selected to the Parade All-America Second Team. He averaged 22. 5 points, 9. 1 assists and 5. 8 steals as a senior, for a total of 2,151 points, 727 assists and 540 steals during his time at St. Patrick, and was named to the Parade All-America second team (for the second year in a row) and was also named a McDonald’s All-American. In the McDonald’s All-American Game of 1996 Holloway was the starting point guard for the East team: he recorded 7 points, 8 assists and 6 steals, receiving the Most Valuable Player award.