Carl "Rex" May grew up on a farm with no other kids around, fostering a love for basketball playing one on none. In 1950, he graduated from Marco High School, where he was on the Marco Bears team that won the only sectional basketball championship in school history.

Following his high school graduation, May began his college education and playing career at Vincennes University, studying business, health and physical education, from 1951-1953. He spent the next two years serving in the United States Army, including 18 months overseas. After his military service, May continued his education at playing career at Oakland City College, playing for the Mighty Oaks from 1955-1957.

After earning his bachelor's degree in secondary education in physical education and health, he started his teaching and coaching career at Oaktown, Indiana, where he served from 1957-1959. During this time, he started his masters degree program at Indiana University, which he completed in 1964.

In 1959, he moved to Midland, Indiana, where he taught from 1959-1963. He then went to Dubois High School, teaching and coaching from 1964-1968. In 1969, he moved to Jasper High School, teaching business and coaching. He retired from coaching in 1984, and from teaching in 1994, and truly enjoyred his years working with students in education and sports.