Jermaine Middleton grew up in the Los Angeles metro area, as he was convinced by his friend and future teammate Dorell Wright to attend South Kent School. As a result, he left Crenshaw High School to finish his high school career on the Hillside.
After graduating in 2004, Jermaine Middleton played two years at Central Connecticut State University, followed by another two years at Northwood University in Palm Beach. Middleton helped Northwood make the final eight teams of the NAIA National Tournament. Then, Jermaine Middleton played for Rochester and St. Joseph of the Premier Basketball League. In 2011, he signed a contract to play with the Harlem Globetrotters, the team he retired with in 2015. Jermaine Middleton currently lives in San Antonio, working in business with the company SafeLace.