In September 1861, Streight enlisted in the Union army as a colonel in the 51st Indiana Infantry. Streight was a prisoner of war at Libby Prison in Richmond, Virginia, for ten months in 1863 and early 1864. He participated in the battles of Shiloh, Perryville and Stone's River. In April 1863 he led 2000 men from Nashville, Tennessee, on what has been known as "Streight's Raid". The raid terminated on May 3, 1863, with the capture of Streight and his command by General Nathan Bedford Forrest. Streight and 107 other soldiers escaped from their barracks by digging a tunnel under the prison grounds. He retired from the army in 1865.