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According to Raine's opening inscription, this leather bound pocket diary was a gift to Charles A. Raine from fellow Fort Delaware prisoner Lt. Henry C. Cromwell of the 10th Kentucky Cavalry on August 4, 1864. Rain had just arrived at Fort Delaware as a Confederate prison of war. The diary is written in both pencil and ink. The first twenty pages are Raine's notes on various subjects of English history. After a gap of blank pages, Raine's diary entries begin on January 1, 1865 and continue until his release on June 17, 1865. The final paragraph of the diary section details his journey home to Virginia. Entries vary in length, averaging a few lines per day, and detail the weather, Raine's physical and emotional state and the miseries of prison life, news of fellow prisoners, preaching and religious exercises in the barracks, letters written and recieved, parcels and money received, news concerning the war and prisoner exchanges, and thoughts on his imprisonment and the future. Notable entries include the news of General Robert E. Lee's surrender and his entries mentioning debate topics and results by a debating club formed among prisoners. The next section of the book includes a letter draft to a friend, a number of pages of poetry, miscellaneous literary excerpts including a page of notable lines of Shakespeare, and some accounting records that may be post-war. The final section of the book includes autographs, addresses, and some personal notes from sixty-three fellow prisoners. The diary also had within it leves a number of loose letters received, poems, notes, etc... written by him and other authors during his imprisonment and in the post-war years.