At the time of the United States entry into World War II, Freeman was in China again, in Beijing as a language student and concurrently as Assistant Military Attaché at the American embassy.

Towards the end of the war in late 1944, he was sent to Rio de Janeiro, Brazil as Director of Arms Training for the Joint Brazil-United States Military Commission, a position he held until October 1947.

He returned to the Army General Staff in Washington D.C., working in the Latin American Branch of the Plans and Operating Division, then from 1948 to 1950, served as a member of the Joint Brazil-United States Military Commission, and was also a member of the United States Army delegation to the Inter-American Defense Board.

At Chipyong-ni the 23rd RCT was cut off and surrounded by elements of five Chinese divisions, which launched fanatical all-out assaults against them.

After his second division command ended in 1957, he served as Senior Army Member to the Weapons System Evaluation Group in Washington D.C.