Having moved with their family to Wisconsin in the early 1850s and abandoned their African American identity, Eston Hemings Jefferson's sons John Wayles Jefferson and Beverly Jefferson fought in white Wisconsin regiments. John Wayles Jefferson rose from major to colonel of the 8th Wisconsin Volunteer Infantry in the Mississippi Valley campaign, at one point commanding the regiment. Two of Madison Hemings’s sons, William Beverly Hemings and Thomas Eston Hemings also served in white Union regiments. Thomas Eston Hemings died in a Confederate prison.
On the other side of the color line, the only three fully-commissioned black officers of the 55th Massachusetts Volunteer Infantry all had connections to the Monticello enslaved community. James Monroe Trotter and William H. Dupree married daughters of Ann-Elizabeth Fossett and Tucker Isaacs, while John Freeman Shorter was a descendant of Elizabeth Hemings through her granddaughter Melinda Colbert Freeman. The chaplain of the 55th Massachusetts called Trotter, Dupree, and Shorter, "three as worthy men as ever carried a gun."
The historian of the 55th Massachusetts described Shorter as having "every soldierly quality, from scrupulous neatness to unflinching bravery. He well merited the reputation of the best non-commissioned officer in the regiment. As such, he was selected for the first promotion from the ranks" in March of 1864. Trotter and Dupree were promoted four months later, after the regiment's first major engagement near Charleston, South Carolina. The War Department refused to officially muster them in as officers "because God did not make them White," as a fellow soldier wrote at the time.
In August Trotter wrote to the son of William Lloyd Garrison that he, Dupree, and Shorter were nevertheless performing the duties for which they were commissioned, "but this half and half arrangement is very unpleasant to us" and "most all the line officers give us the cold shoulder." A year later several white officers threatened to resign if Shorter, Dupree, and Trotter were mustered in as lieutenants. "[We] will try to do our duty as officers," Trotter wrote, "let prejudice be as great as it may." Only in the summer of 1865, when the fighting was over, were they officially commissioned.
The men in the Massachusetts 54th and 55th regiments soon learned of a significant “breach of faith” on the part of the government they were serving. They had enlisted on the understanding that they would be paid, equipped, and treated on an equal footing with white soldiers. By the fall they knew that the War Department had decreed that their effective pay was to be half what white soldiers received. This issue, highlighted in the film Glory, produced many months of simmering unrest and letters and speeches of protest, with conspicuous participation by Shorter and Trotter. Both Massachusetts regiments refused to accept any pay until allowances were equalized.
There was great rejoicing in the camp on Folly Island when they were finally paid in full in October, with a program of speeches, singing, and music by the regimental band, of which Dupree was manager. John Freeman Shorter read the regiment's resolutions, which included their first duty as men, to "prove our fitness for liberty and citizenship, in the new order of things now arising in this, our native land."
The chance to prove themselves came only three weeks later, in the Battle of Honey Hill, near Charleston. Federal troops withdrew in defeat after a fierce battle in which the 55th suffered the highest proportion of casualties. In his vivid account, William Wells Brown singled out the gallantry of several men. "Sergeant-major Trotter is wounded," he wrote, "but still fights. Sergt. Shorter is wounded in the knee, yet will not go to the rear."
Although disabled by his leg wound, Shorter stayed with the regiment until it was finally mustered out in August 1865. But his life was cut tragically short. On the way back to Ohio to get married, "he was exposed to the contagion of the small-pox, which his constitution, weakened by wounds, could not resist; and, soon after arriving at his destination, he died." After mustering out, Dupree and Trotter returned to Ohio to marry the Isaacs sisters, Maria Elizabeth and Virginia. They settled in Boston where both men found positions with the United States Postal Service.