 When Tex Rickard began promoting boxing at the old Madison Square Garden in 1925, Humphreys was hired as official ring announcer and was present at many of the top prize fights held at the venue including Jack Dempsey's bouts against Georges Carpentier, Luis Firpo and Gene Tunney.He was a major fan of Gene Tunney and Jack Dempsey, regarding the latter as "the most devastating fighter ever to step in the ring".He often claimed that Dempsey's bout against Firpo was "the most exciting he had ever witnessed".