Letter from Harry Harris to President William McKinley regarding John Patterson Osterhout running for postmaster in Belton, Texas. He endorsed John's run for office and told President McKinley that the appointment would be favorable.

Letter from Pelatiah Osterhout to cousins and friends discussing their family. He was a distant relative and was contacted by John Paterson Osterhout. He told them about his life and the origin of the Osterhout family. Included is an envelope addressed to "John P. Osterhout."

Letter from Chloe Smith to her uncle, John Patterson Osterhout, discussing the family. She wrote about how she and her mother were coping with the loss of her father. She told him that his son, Paul, had returned home. Included is an envelope addressed to "Mr. J. P. Osterhout."

Letter from Sarah Osterhout to her brother, John Patterson Osterhout, discussing troubles she has been having. She asked if she could buy his share of land and that money was tight for her. John's son, John Jeremiah Osterhout, and Jeremiah's daughter had succumbed to illness and Sarah wanted to know what her brother wanted to do. In the post-script, Sarah mentioned that her brother had begun a lawsuit against her and wished he would wait. Included is an envelope addressed to "Mr. John P. Osterhout."