He secured a job as a mechanic at Lake Buick, a dealership on Lavern Avenue on Cleveland's West Side, and on July 15, 1947, obligated to Local Lodge 1363 of the International Association of Machinists and Aerospace Workers.
Union officials quickly recognized Winpisinger's talent and appointed him to the National Field Staff, as a Special Representative, in 1951, and assigned him to organizing tasks in Ohio, Michigan and Pennsylvania.