Letter from E. M. Drayton to President William McKinley regarding John Patterson Osterhout applying for the position of postmaster in Belton, Texas. He wrote that he could think of no one better to fill the position.

Letter from John Patterson Osterhout to his brother regarding land in Texas. He sold a couple hundred acres out of the 400 acres he bought a few years earlier. He wrote about other land he had bought and the cheap pricing of land in Texas. An uncle of theirs was thinking about moving to Texas and John agreed that he should and could get a lot of land for his money. He gave some advice for his uncle if he chose to move to Texas and recommended he should have a few thousand dollars before coming. At the end of the letter, John wrote about several pieces of furniture and cattle he purchased.

Letter from J. W. McDade to Headquarters concerning Private John Patterson Osterhout's detachment. The brief message stated that John was officially detached from his unit and had to report back to his company after seven days.

Letter from Paul Osterhout to his father, John Patterson Osterhout. He wrote to his father because his mother was sick with a cold and unable to write. Paul a brief summary of local news that included recent deaths and a musical performance that was happening soon.

Letter from John Patterson Osterhout to his daughter, Gertrude Osterhout, with news from home. Everyone at home at been well, except for her mother who had a cold. They had four cows that they milked and used the milk to make butter to sell. He told his daughter that she should not be so eager for school to be over. He concluded the letter by correcting his daughter on her use of the word "too."