Bailey was a top scoring forward for the Big Red during his years on East Hill. Stepping into a prominent role in 1943 with the graduation, transfer and attrition of players due to World War II, he was relied upon to carry the Cornell attack. He led the squad with five goals in 1943, helping the team to a 6-1-1 mark. He continued to put up strong numbers in 1944, helping the squad to a 6-1-0 record en route to earning Second Team All-America honors. He trained as a Naval cadet, although it is not known whether he went on to serve during war.
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