The collection consists of two diaries written by Jeffery T. Wilson, one from 1913 and one from 1928. Diary entries cover a range of topics from the daily life and health of Wilson and his family, to his opinions on race, race relations, politics (especially in and around Portsmouth and Norfolk, Virginia), segregation and the Jim Crow South, and religion (many entries begin with biblical quotations).

Entries for the 1913 diary were kept in a Wanamaker's Diary (produced by the department store chain) actually designed for 1911. As a result, Wilson has hand-corrected the days of the week throughout to reflect 1913. The diary includes advertisements, as well as a history of the Wanamaker stores. A map of the store locations in New York City was removed from the diary during preservation, but is included in the collection as a separate item.

In addition to the entries recorded (two to a page), throughout the year, Wilson attached additional pages to continue writing. Many of these consists of reminiscences of his life in previous years on topics from the Civil War, his service in the U. S. Navy, segregation and race issues in Portsmouth and Norfolk, and local news. He also writes of daily events: his family's health, church events, the weather, and his frequent concerns about money. Several entries from the 1913 diary are quoted below:

Forty seven years ago the colored folks of Norfolk and Portsmouth celebrated the passage of the "Civil Rights Bill" by Congress and we all gathered in the city of Norfolk. had a big parade of civic societies, and discharge colored soldiers speaking out on the suburbs. The poor whites "sicked on" doubtless, by the upper class, interfied with us. tried to break us up. a riot ensued and several whites were killed. I was unhurt. Who killed the parties was never known. but several colored men left the city for fear of arrest. and have never returned. (April 2, 1913)

Fifty one years ago I was a body servant for A. P. Grice, who was an officer in Cohoon's Battalion C.S.A. encamped on "Dunn's Hill," near Petersburg. I had just been released from the Richmond City Jail. Where I had been confined two months. held as a witness in a murder case and that kept me out of the U. S. Army. Where probably I would have been killed or wounded. (May 13, 1913)

Wife bought a bed for Wendell. and he went to sleep in it. It seems as if I am to be the daddy of babes all my life from present indications. Well, if the Lord says so his Will be done not mine-- (July 28, 1913)

Thirty eight years ago my brother and me met for the last time and as far as I know he is yet alive. Robt I mean, he is 72 years old. (October 1, 1913)

A womans life is of very little value in Norfolk even if she is white and a wife. (October 14, 1913)