On November 1, 1943, he saw his first combat when his unit came ashore at Torokina on Bougainville in what were the first battles of the Bougainville Campaign. A few days later, while he was leading a patrol, he encountered a group of five or six Japanese soldiers in a clearing. An exchange of gunfire followed, and Freeman was wounded in the jaw and left arm. Eventually, he was evacuated to a US Army hospital on New Caledonia and then to a Naval hospital on Nouméa. He returned to the United States in 1944 but never recovered enough movement in his arm to pass a US Marine Corps physical to return to combat.