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The bulk of the Andrew C. L. Gatewood papers consist of 28 letters (dated 1860-1864) written by Gatewood to his parents and other family members. Early letters describe life at VMI and in Lexington, Virginia, just prior to and during early months of the Civil War. Subsequent letters date from Gatewood's service with the 11th Virginia Cavalry Regiment, Company F (Bath Squadron), including a letter (dated September 1862) written after the Second Battle of Manassas (2nd Bull Run).

The bulk of the Charles A. Derby papers consists of Derby family correspondence. Approximately twenty-eight letters were written by Charles A. Derby (dated 1844-1862) and cover the period from late boyhood up to his death in battle in 1862. Included are letters (dated 1846-1847) written while he was a cadet at VMI, as well as correspondence dating from his careers as a teacher and Episcopal clergyman. Two items were written during his brief service in the Confederate Army.

The collection consists of related to three members of the Fulkerson family: Samuel Vance Fulkerson (1822-1862), his brother Abram Fulkerson, Jr. (1834-1902), and Abram's son, Samuel Vance Fulkerson (1863-1926). Significant items include:

• Civil War correspondence (dated March-May 1862) written by Samuel V. Fulkerson (1822-1862)
• Samuel V. Fulkerson's (1822-1862) reports of the Battle of McDowell and the Battle of Winchester (dated May and June 1862)
• Wartime correspondence (dated 1863 and 1865) written by Abram Fulkerson, Jr. Two letters were written while he was a prisoner of war.
• A letter of appreciation (dated September 1862) written by General Stonewall Jackson following Samuel V. Fulkerson's (1822-1862) death in battle

• Battles of Port Republic and Kernstown
• Death of Turner Ashby
• Refugee and civilian life
• Camp life
• References to Stonewall Jackson, including Samuel V. Fulkerson's (1822-1862 assessment of his character and Abram Fulkerson, Jr.'s reflections following the Jackson's death

This collection consists of correspondence of Confederate soldier Henry H. Dedrick, a Private in the 52nd Virginia Infantry Regiment. A bulk of the correspondence consists of letters to and from his wife, Mary E. A. Dedrick (Balsley) ("Lissa" or "Lizza"). Subjects include camp life, regimental activities, family and personal news, and hardships endured by civilians. The letter dated May 10-11, 1863 mentions the wounding and death of General Stonewall Jackson.

The James H. Reid papers consist of the Civil War correspondence (18 items) of Reid. Included are 14 letters (dated August-November 1862) from Reid to his parents written while he was a fourth classman at VMI. This correspondence contains many references to wartime cadet life, including the use of the term "rat" as a name for new cadets, hazing, uniforms, food, guard duty, and other aspects of life at VMI.

The James W. Massie papers consist of the personal papers (40 items) of Massie, including:

• Incoming correspondence (1855-1857)
• Civil War papers, primarily incoming letters, orders, and commissions (1861-1863)
• Post-War papers, including letters written by Massie's wife, Sophonisba Breckinridge McDowell (Massie), and documents related to their son, James McDowell Massie
• Confederate bonds
• Envelopes

The John E. Roller papers include:

• Civil War era letters from cadet friends concerning life at VMI
• Civil War dispatches and telegrams that date from Roller's service with the Confederate States of America engineers, including one document signed by General Robert E. Lee
• One scrapbook (circa 1910) that contains clippings about Civil War battles, veterans, unit reunions, monument dedications, and other related information
• Two photographs, one of Confederate soldier Lieutenant Colonel Samuel T. Walker (10th Virginia Infantry Regiment) and one of the Virginia Legislature Centennial Committee (1871)
• Holograph text of a cadet literary-debating society speech delivered by Cadet Norwood B. Randolph in 1870
• Other items

The John J. Clarke Civil War papers consist of documents, including commissions, military orders, correspondence, and dispatches that relate to activities in and around Charleston, South Carolina during the period of 1864 to 1865. One letter (dated February 4, 1865) to Colonel Clarke from Headquarters discusses proposed training of African-American troops in the Confederate States of America Corps of Engineers.