 On November 1, 1917, Brennan first defeated Joe Bonds at the Unity Cycle Club in Lawrence, Massachusetts, in a second-round knockout.On April 28, 1917, he defeated Bonds again at the Broadway Sporting Club in Brooklyn, New York, in a ten-round newspaper decision.On December 20, 1918, Brennan achieved a newspaper decision third-round TKO against Bonds by the "Syracuse Herald" at the Arena in Syracuse, New York.