Easterday was born in Lisbon, Ohio. He was an all-state basketball player and held the state record in the pole vault. Before enrolling in college, Easterday also played on sandlot and hometown teams from Ambridge, Salem, Beaver Falls and other western Pennsylvania and eastern Ohio teams. Pitt's undefeated 1917 team was known as "The Fighting Dentists" because on occasion every position was filled by dental students. The dental students on the 1917 team included Easterday, Skip Gougler, "Tank" McLaren, "Jake" Stahl. and Jock Sutherland.