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- [Letter from Chaplin F. Phillips to John Patterson Osterhout, May 14, 1897]
- Letter from Chaplin F. Phillips to John Patterson Osterhout discussing his family. Chaplin was glad to find another one of his father's friends and told John that he would like to speak with him. He told John that if he was ever in Chicago he should come visit.
- [Letter from E. A. Osterhout to John Patterson Osterhout, August 22, 1890]
- Letter from E. A. Osterhout to John Patterson Osterhout asking if family John was a part of the New York state family. He told John the name of his father and grandfather and that he would be interested in hearing from him again. Included is an envelope addressed to "Hon. J. P. Osterhout."
- [Letter from H. J. Bardwell to John Patterson Osterhout, December 8, 1896]
- Letter from H. J. Bardwell to his cousin, John Patterson Osterhout, regarding their family tree. Bardwell had been spending his time in the library trying to trace the Osterhout family back to the first settler and shared what he had found so far. He asked John for clarification on what he had told Bardwell about the family before and hoped to hear back soon.