He also owned the Prince Hotel, Bismarck.
The first three black players to join the Bismarck Churchills were Quincy Trouppe (Chicago American Giants catcher, Red Haley (Memphis Red Sox (infielder), and Roosevelt Davis (Pittsburgh Crawfords) pitcher. When these proved insufficient to beat Bismarck's great rivals in Jamestown, Churchill recruited Satchel Paige from the Crawfords. Gus Greenlee, the Crawfords' owner, threatened to knife Churchill for the 'theft' of Paige.
Paige arrived from Chicago on the day of the game in October 1933. It was the first time that he had played alongside white players. Churchill won his bet of $1000 with a Jamestown politician that his team would win. A rematch was held a few days later in Jamestown before a crowd of 4000. After twelve innings the game was ended, unresolved, by darkness. Churchill challenged Jamestown to a three-game series in Bismarck. Bismarck won that series and the state championship.
Next season (1934), Churchill spent $5,000 (using personal and city funds, and federal emergency relief labor) improving on the Bismarck ball park. He built a 3000-seat grandstand, children's bleachers, and a 500-space car park, with a clear view of the game along the outfield fence.
Churchill's 1935 team included Satchel Paige, Hilton Smith, Quincy Trouppe (who joined the team in early June), and Ted "Double Duty" Radcliffe (who joined on June 21 after securing his release from the Brooklyn Eagles).