This collection contains approximately three hundred and fifty letters written from 1938 to 1945, primarily by Lawrence Winston to his wife Cecelia Winston. Additionally, the collection includes several letters written by Lawrence to various relatives (his mother, father, daughter Pat, and father-in-law) and several letters written to Cecelia from her relatives.

The correspondence contains a number of letters written while Lawrence was stationed at Pearl Harbor, from pre-war through early 1942. Although there are no descriptive letters about the attack, the collection contains two items from December of 1941. As all mail was censored for sensitive material during the war, Lawrence Winston does not write about his location or activities. Therefore, much of the content of the letters of this period regards his personal feelings towards his wife and daughters and domestic issues such as finances.

Highlights of the correspondence include: a 1938 letter describing the negro condition in Panama and the nature of Panamanians in general; descriptions of the natives in Port Au Prince and their differing treatment of negroes and whites; a letter dated November, 1941 discussing the delicate war crisis written after Lawrence's return from Japan; descriptions of his physical and mental deterioration due to bombings and the stress of being away from home for nearly four years straight; and some letters revealing the experience of African American sailors in the Navy.

In addition to the typed and hand-written letters the collections contain 40 V-mails, several telegrams and postcards, and a few ephemeral items.