From NKAA, Notable Kentucky African Americans Database (main entry)
Churchill, Leroy O.(born: 1918 - died: 1987) Leroy O. Churchill was the first African American guard at the Bridewell Prison in Chicago, IL, and he was also the first to become a captain. Churchill was head of the 1st division of the west cell-house, where he supervised eight guards and 445 inmates of whom 40% were African Americans. Churchill reported directly to Warden Fred K. Hoehler. "Bridewell" is an English term from the 1500s for "jail" or "house of corrections." The earliest Bridewell Prison was located in London, England [info]. Bridewell, the city jail of Chicago, was built in 1852 as a short-term facility for offenders of minor crimes. In 1959, when it held 1,700 prisoners, Leroy O. Churchill was one of the six captains at the facility.
Churchill was born in Paducah, KY, the son of Roscoe Conkling Churchill and Elizabeth B. Churchill, a hairdresser. The family moved to Chicago in 1920, then returned to Paducah after Roscoe Churchill died. The Churchill family had been in Paducah for several generations; family members are listed in the 1914-1915 Caron's Paducah City Directory as living at 1036 Washington Street; the residents included Ora; Marshall Sr. (1866-1911); Emma (b. 1867); Loyd (b.1889); Roscoe (b. 1885); and Sherman Churchill (1887-1927). When the family moved back to Kentucky, Leroy attended Lincoln High School, where he excelled in football, basketball, track, and boxing. He was awarded an athletics scholarship to attend West Kentucky Industrial College [now West Kentucky Community and Technical College] where he was an outstanding football player.
After his graduation, Leroy Churchill returned to Chicago, and in 1948 successfully completed the civil service exam, ranking second, and was appointed a guard at Bridewell Prison. He received the rank of captain in 1951. Leroy O. Churchill was the husband of Mary Hopkins Churchill, a beautician; the couple had two sons. For more see R. Ottley, "Negro guard captain aids his charges in Bridewell," Chicago Daily Tribune, 03/14/1959, p. W Part 5 - p. 12F; and the Cook County Jail History website.