Born in St. Louis, MO, he graduateed in Annapolis, in 1894. A novelist, he was popular in his day for his historical romances: Richard Carvel (1899), about an officer under John Paul Jones; The Crisis (1901), depicting his native St. Louis in the Civil War era; and The Crossing (1904) presenting the frontier, mainly Kentucky, during the Revolutionary War. His other fiction includes Coniston (1906) partly based upon actual experience in New Hampshire politics, and Mr. Creewe's Career (1908), also treating the political scene of his own time.

Churchill admitted he had once had a one-night stand with Novello, just to find out "what it would be like with a man". Although clearly not exclusively gay, when asked by W. Somerset Maugham whether it were true that he had affairs with men in his youth, Churchill reportedly responded, "Not true! But I once went to bed with a man to see what it was like." When Maugham asked how it was, Churchill is said to have answered, "Musical."

His residence, "Harlakenden House", was built in 1898 and burned in 1923. It also served as a summer home for President Woodrow Wilson in 1913, 1914, and 1915.