When he announced that he wanted to play football for "Pop" Warner, his comments initially "invoked some chuckles from officials there.

[3] The dental students on the 1917 team included Easterday,[4] Skip Gougler,[5] "Tank" McLaren,[6] "Jake" Stahl.

[9] From 1929 to 1933, Easterday coached football and basketball at Kittanning High School, located 44 miles (71 km) northeast of Pittsburgh.

He coached the Kittanning Wildcats to their first undefeated, untied season in which they allowed only 12 points scored against them the entire year.

[2] Easterday also practiced as a dentist in Kittanning, Pennsylvania in the 1930s, and worked for a couple of years with the National Youth Association.

From 1937 to 1942, he worked for Allegheny Ludlum Steel and from 1942 to 1959, Easterday was a safety supervisor at the Pullman-Standard Company in Butler, Pennsylvania.

Easterday had begun his coaching career at Hardin-Simmons College near Odessa and met his wife there.