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Bailey earned his first All-American accolade, placing 27th overall out of 278 runners over the 8,000-meter course at the 2016 NCAA Cross Country Championship in an impressive time of 24:48.4 on Saturday, Nov. 19. He became RIT's first All-American since Matt Giannino in 2014. Bailey was 37th after the 2,000-meter split (6:05.7), 19th at the midway point (12:47.8), and 15th overall at the 6,000-meter split (19:12.8). He was the second best Liberty League finisher and third place finisher among all Atlantic Region runners.