John Freeman Shorter was raised in freedom in Washington, D.C. In 1863 he left Delaware County, Ohio, for Boston, in order to enlist in one of the first black regiments to be organized, the 55th Massachusetts Volunteer Infantry. He became one of only three fully-commissioned black officers in the regiment; the other two lieutenants, James Monroe Trotter and William H. Dupree, were also connected to Monticello.
Despite promises of equal treatment, the pay of the men of the Massachusetts regiments was half that of white soldiers and Shorter, like Trotter, became a leader in the fight for equal pay. He was wounded at the Battle of Honey Hill near Charleston, South Carolina, in November 1864. After being honorably discharged in 1865, he returned to Ohio to marry his fiancé, but died within weeks of reaching home. Shorter's brother Charles Henry Shorter served in the 22nd U. S. Colored Infantry and survived the war to be an officer in a Washington post of the Grand Army of the Republic.