John O'RILEY was born August 28, 1850 in Savannah, Chatham County, Georgia, the son of James O'RILEY (born about 1820 in Dublin, Ireland; died before August 15, 1899 in Savannah, Georgia) and Sarah (RICE) O'RILEY (born about 1822 in South Carolina; died 1878 probably in Savannah, Georgia).

John left Savannah and after working for a while in Key West, Florida, migrated to Durant, Blue County, Choctaw Nation, Indian Territory (later to become Durant, Bryan County, Oklahoma with Oklahoma statehood on November 16, 1907) in 1876 to work on construction of the bridge across the Red River between Oklahoma and Texas, just south of Durant. While he was there, he met twice-widowed Mary Catherine (HARKINS) NAIL WILLIS. They married on November 17, 1878 after knowing each other for only two weeks. Nine children were born of that marriage: Ada O'RILEY (1879-1880), Cora O'RILEY (1881-1881), Arlee (O'RILEY) REED BOYET (1883-1972), Lester Roy O'RILEY I (1885-1960), Zula (O'RILEY COOPER (1888-1972), Lula (O'RILEY) AUSTIN (1890-1968), Lela Josephine (O'RILEY) McINERNEY (1892-1986), Ora Catherine O'RILEY (1894-1964), and Zelma O'RILEY (1897-1991).

In light of the fact that John's wife Catherine was 1/2 Choctaw Indian, he was an original enrollee of the registration of the Five Civilized Tribes by the Dawes Commission as an Intermarried White (IW). He and his family were registered on September 12, 1903. Their names appear in field #3449 of the Dawes Choctaw Rolls. His enrollment is listed as #IW329.

John was shot by his son-in-law Major Frankness "Frank" REED and died shortly thereafter as a result of his wounds on January 19, 1904 in Durant, Blue County, Choctaw Nation, Indian Territory at the age of 53.