Freeman served in the US Army Reserve for 18 years and deployed to Iraq in August of 2006. He was part of a route clearance platoon operating in the Al Anbar Province, primarily in and around Fallujah. As commander of the lead vehicle, his job was to identify IEDs and other threats. Freeman was personally responsible for clearing 40 IEDs. Some of them got past him, and he sustained six direct hits resulting in three ‘grade 3’ concussions and Traumatic Brain Injury. After the last blast he was airlifted to Germany for a possible brain bleed. In Germany they ruled out a brain bleed but determined he had sustained too much brain damage to return to combat.