[1] Woolams attended the University of Chicago for two years before joining the United States Army Air Corps.

He served on active duty for approximately eighteen months, after which he returned to the University of Chicago and graduated with a degree in economics in June 1941.

[6][7] Woolams died on August 30, 1946, in the crash of the modified P-39 Cobra I race-plane during a practice flight for the National Air Races in Cleveland, Ohio, that were to occur the next day.

Woolams flew the Cobra I from Cleveland back to Bell Aircraft in Niagara Falls on August 29, after obtaining a disappointing qualifying speed of 392 miles per hour (631 km/h).

Woolams was testing the plane over Lake Ontario late in the afternoon at speeds over 400 miles per hour (640 km/h) when it suddenly and inexplicably crashed into the water, breaking apart upon impact.