Crenchaw was born to Reverend Joseph C. Crenchaw and Ethel Pitts Crenchaw at Little Rock, Arkansas, in 1919. His father was a local civil rights leader with the NAACP who was president of the Little Rock Chapter during the Little Rock Central High School Crisis, and a professional tailor. His mother was a beautician. Crenchaw had three siblings. He graduated from Dunbar High School (the local black high school) in 1936. After graduating, he attended Dunbar Junior College where he received a teaching certificate in auto mechanics. After leaving Dunbar Junior College, Crenchaw pursued a bachelor’s degree in mechanical engineering at the Tuskegee Institute in 1939. He did not receive a degree, however because he postponed his academics to pursue becoming a pilot. Crenchaw was the first Arkansan to arrive and to graduate fromMoton Airbase in Tuskegee, Alabama.