The collection includes 45 envelopes, one card, and one sheet of paper, with a drawing on each side, for a total of 49 drawings. Wakefield produced the drawings from 1917 to August 1918, at Camp Pike and Fort Dix, before he deployed to Europe. The drawings are listed in chronological order in the item list. Digital images of each drawing are available. Rudie Wakefield continued to use his artistic skills when he entered the U.S. Army, producing detailed, often humorous, scenes about military life mostly on the envelopes of the letters he sent home to his mother. Rudie signed and dated most of the drawings with the year of creation. The dates used in the item list are taken from the envelope postmarks or from the drawings. Only one envelope in the collection is addressed to Rudie’s father, “Digging In” (c.22 June 1918). Rudie included holiday scenes on some envelopes (28, 30 Dec 1917, 19 Jan 1918). A few other images do not relate directly to military life, such as a dragon (15 March 1918) and polar bears (18 Jan 1918). Before being donated to the Missouri Historical Society, the drawings were exhibited at the James Island Arts and Cultural Center in James Island, South Carolina.