[1][2][3] Born in Danville, Kentucky, Woolpert was raised in Los Angeles, graduating from Manual Arts High School in 1933, in the depths of the Great Depression.

Junior College and Loyola University, where he played basketball for three years, was initiated into the Alpha Delta Gamma fraternity, and graduated in 1940 with a degree in political science.

Woolpert's teams, anchored by Bill Russell, K. C. Jones, Gene Brown, and Mike Farmer, were known for their defense and held opponents below 60 points on 47 different occasions.

[1] While at USD, Woolpert posted a 90–90 record and served as both men's basketball coach and athletic director.

Woolpert retired from coaching in 1969, and later settled down on the Olympic Peninsula in Washington and became a school bus driver in Sequim.