Jimmy Cunningham has lived in Baldwyn his entire life. He graduated third in his class of 26 from Baldwyn High School in April 1944 at 17 years of age. At the time of his graduation, World War II was in progress and thousands of young men were being drafted. He had until November to decide if he wanted to be drafted or join one of the U.S. Armed Forces. In July, he decided to join the Navy.