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This collection consists of one original charcoal sketch (circa 1908) by Cadet Frank A. Fickes that was published in the 1911 VMI yearbook. The sketch features a skull, snakes, and ghost, which are symbols of "TKL," a cadet secret society.

This collection consists of the personal papers (1929-1935) of Henry M. Stewart, Jr., VMI Class of 1935. The collection includes memorabilia from Stewart's high school years at the Staunton Military Academy (Virginia) and his cadetship at VMI. The VMI material includes a scrapbook, dance and athletic programs, drawings, photographs, information about the Class of 1935 ring design, and other mementos.

The James H. Waddell papers consist of four items, including:

• A letter (dated 1855) from Waddell to his sister that contains a detailed description and pencil drawing of his room (#14) in barracks and of his roomates (Barksdale, Penn, Magruder, Shepherd, and Wilson)
• A drawing of a barracks room and roommates
• Pencil map, 8 inches x 10 inches, labeled "Plan of Battle of Bethel Church, June 10, 1861"
• Letter of recommendation (dated 1879) written by VMI's Superintendent Francis H. Smith and endorsed by Board of Visitors President John Letcher

This collection (five items) consists of items related to James J. Phillips, including:

• VMI Diploma (1853)
• VMI Society of Cadets certificate (1853)
• A drawing of VMI Barracks (circa 1852-1853)
• Confederate Army Commission (1863)
• Certificate, Pickett Buchanan Camp, Confederate Veterans (1890)

The collection consists primarily of items (approximately 20) from John H. Kyle's VMI cadetship (1919-1923), including a scrapbook, grade reports, sketchbook with pencil drawings of cadets and cartoons depicting VMI life, and photographs. The collection also includes documents (1923-1937), including a letter from Frank McCarthy, VMI Class of 1933.

The John L. Cochran papers consist of:

• One report card (1879) from the secondary school Cochran attended before entering VMI
• One letter (dated September 4, 1880) from Cochran to his mother
• One diary with sketches (1881) that contains short and sporadic entries made while at VMI
• Four volumes of class notes (1882-1885) taken while Cochran was a student at Swarthmore College (Pennsylvania) and the University of Virginia, with some examples of poetry and sketches interspersed

This collection consists of 17 watercolor and pen/ink drawings by Cadet Levin J. Houston. Several of the drawings were featured in the cadet magazine known as "The Sniper" that was published during the 1920s.

The Richard T. Goodwyn papers consist of 18 pencil and ink drawings by Goodwyn and one letter (dated March 28, 1896) from VMI Superintendent Scott Shipp to Goodwyn.

This collection consists of the papers (30 items) of Robert E. B. Stewart. The collection includes a notebook containing orations delivered before VMI cadet debating societies, drawings completed as class assignments at VMI, and a few clippings concerning his life after he left the Institute.