Sonny moved to Chicago for a few years to remove himself from the surrounding elements of negativity around the Jazz scene. He reemerged at the end of 1955 as a member of the Clifford Brown-Max Roach Quintet, with an even more authoritative presence. His trademarks became a caustic, often humorous style of melodic invention, a command of everything from the most arcane ballads to calypsos, and an overriding logic in his playing that found him hailed for models of thematic improvisation.
It was during this time that Sonny acquired a nickname,”Newk.” As Miles Davis explains in his autobiography: “Sonny had just got back from playing a gig out in Chicago. He knew Bird, and Bird really liked Sonny, or “Newk” as we called him, because he looked like the Brooklyn Dodgers’ pitcher Don Newcombe. One day, me and Sonny were in a cab…when the white cabdriver turned around and looked at Sonny and said, `Damn, you’re Don Newcombe!” Man, the guy was totally excited. I was amazed, because I hadn’t thought about it before. We just put that cabdriver on something terrible. Sonny started talking about what kind of pitches he was going to throw Stan Musial, the great hitter for the St. Louis Cardinals, that evening…”