The Sherry papers includes 50 letters written by Robert Sherry to his wife, Caroline, and two to a friend, Oscar. The eight remaining items in the collection include letters and documents addressed to Caroline Sherry regarding the death of her husband and arrangements to receive a widow's pension.
Sherry was a rough-edged man, whose strong personality is reflected in the tintype that accompanies the collection, in which he stands glaring at the camera, leaning casually against his rifle, pistol stashed in his belt. Sherry writes what he feels without reservation, even when those feelings are murderous, and as a result, his letters are always interesting to read. His candor in discussing the problems in the regiment and his deep hostility toward officers provides a particularly valuable insight into the mind of many soldiers subjected to harsh conditions and to the extraordinary military inefficiency and arbitrariness that characterized some units.
Personal finances were among Sherry's greatest concerns, and the money offered to recruits may have been the primary factoring in inducing him to enlist and reenlist. He is vocal about the fact that he is not fighting for "adam nigger" or for the Republican Party, and he berates his wife because she no longer denigrates Blacks in her letters. He relished the opportunity to loot an elegant Virginia home in October, 1861, and wrote proudly of having taken $2,000 in Confederate money from a dead Virginian, which he buried by the banks of the Rappahannock, should he ever return. Sherry talked of returning to Virginia after the war, where he had been assured by a plantation overseer that he could make an easy living and high wages.