Letter from J. Z. Miller to unknown discussing the work of John Patterson Osterhout. Miller told the gentleman he was writing that John was a respectable judge and had done good work.

Letter from George Robinson to Judge John Patterson Osterhout regarding the trustworthiness of John. The letter is short and simply states that the judge was deserving of respect and was held in high esteem.

Letter from F. M. Law to President William McKinley regarding John Patterson Osterhout applying for postmaster in Belton, Texas. He gives John a high amount of praise and states that he has the support of the administration of Baylor College.

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 Silas O. Osterhout to his cousin, John Patterson Osterhout, about tracing the family line of Osterhout. Silas believed that if they did, they would be able to gain a great deal in inheritance. Included is an envelope addressed to "J. P. Osterhout ESQ."

Letter from A. B. Dickson to John Patterson Osterhout regarding a recent trip to Texas. Dickson planned to buy land in Texas and wanted to speak with John and visit him next time he visited the state. Included is an envelope addressed to "Hon. John P. Osterhout."

Letter from Elizabeth to her brother, John Patterson Osterhout, regarding a death in the family. She wrote that she was grateful she had children to take care of her after her husband died and that once the estate was settled, there would not be anything she could use to take care of herself with. Included is an envelope addressed to "Mr. John 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."

Letter from Sarah Osterhout to her brother, John Patterson Osterhout, concerning her difficulties. Sarah had been spending the past several weeks taking care of John's son, John Jeremiah Osterhout, and Jeremiah's daughter, Rua. She was having financial difficulties due to Jeremiah's debt and medical expenses. She needed to send her brother money for property that had been sold, but felt he was asking for too much. Included is an envelope addressed "Mr. John Osterhout."

Letter from Gertrude Osterhout to her cousin, George E. Osterhout, discussing a loan. Gertrude wanted to borrow a few hundred dollars from George and would be grateful if he would lend it. She intended to write him a longer letter when the weather improved. Included is an envelope addressed "Mr. Geo. E. Osterhout."

Letter from D. P. Marcy to John Patterson Osterhout regarding a debt he wanted collected. Marcy had someone who owed him money and requested that John collected the money for him. He then wrote about how his family was doing and that a family member was sick.