Freeman was the chief engineer of the Habana at the time it was purchased by the Confederacy. Semmes convinced him to help refit that vessel as the CSS Sumter. He agreed to stay on as that ship’s Chief Engineer. After that ship was laid up at Gibraltar in 1862, he served in the same position on the CSS Alabama. He was captured when the Alabama sank. He did not seek a parole and was held as a prisoner of war at Fort Warren, Mass., until the end of the war. After the war, he worked as an engineer for a steamship line out of New York.