Born in Chicago, Illinois, Freeman as a young child was exposed to jazz. His father, George, a city policeman, was a close friend of Louis Armstrong with Armstrong living at the Freeman house when he first arrived in Chicago.
Freeman’s father taught him to play piano and bought him his first saxophone when he was seven. His musical education was furthered at DuSable High School, where his band director was Walter Dyett. Freeman began his professional career at the age of 16 in Horace Henderson‘s Orchestra.
Freeman enlisted into the Navy during World War II and was trained at Camp Robert Smalls in Chicago. “All the great musicians ended up at Great Lakes”, he recalled. “It was an incubator for the best and the brightest lights in the jazz world at that time, and the musical jam sessions were simply phenomenal.” After training, he was sent to Hawaii as part of the Hellcats stationed at Barbers Point Naval Air Station in a band that starred Harry “Pee Wee” Jackson, the trumpeter from Cleveland whose nickname was Gabriel. The Hellcats were frequent winners of the islands’ competitive Battle of the Bands competitions and included musicians who had formerly played in bands fronted by Duke Ellington, Fletcher Henderson, Ella Fitzgerald, Lucky Millinder, Les Hite, Count Basie, Fats Waller, and Tiny Bradshaw.