Stewart's first outfit of his own was formed in 1918. He had great success at signing long-range contracts with venues, lucrative situations that allowed him to lure the best players away from other bands, including sidemen of his mentor Parker. In 1923 Stewart opened in Chicago with the first black orchestra of its sort to blow through the Windy City, performing a kind of melodic, classical-influenced jazz that would later become something of a sensation for the bandleader Paul Whiteman. The program included a complete performance of George Gershwin's Rhapsody in Blue. Stewart's hit Chicago run came to an abrupt end when lawman Elliot Ness shut the club down for prohibition violations. By the late '20s the bandleader had returned to his native Ohio; pundits cite his refusal to hire a fresh young trumpeter named Louis Armstrong as the beginning of Stewart's decline, both artistically and commercially.
Yet Stewart still had some spark in him, revving up new versions of his group with the addition of great players such as tenor saxophonist Chu Berry and drummer Sid Catlett. The integrity of this group was violated during an extended run in New York City, the musicians' union insisting that half the players be replaced by locals. Such an edict might drive any bandleader to drink -- apparently in Stewart's case he didn't need much convincing anyway, alcoholism another of the main reasons for his decline as a bandleader. His later years were spent as a keyboard soloist, usually in first-class hotels and nightclubs, as well as a teacher of both organ and piano. He was a noted virtuoso, supposedly enjoying freaking out listeners by playing two different melodies simultaneously with his left and right hand. ~ Eugene Chadbourne, Rovi