Starting in the King Features bullpen in 1918, Winner worked with King Features for the next 38 years. At the time of E. C. Segar's illness and death, he was a ghost artist on Thimble Theatre during 1938 and 1939, continuing on some of the strip's Sunday pages in 1940. Winner also authored other long-running strips such as Tubby, Daffy Doodles and Elmer aka Just Boy. Dell's Large Feature Comic reprinted his Thimble Theatre in 1941 and 1943.
In the last years of his life, Winner drew The Katzenjammer Kids, from 1947 to 1956. Winner lived with his wife, the former Agnes Reid, and two daughters in Upper Montclair, New Jersey. He died of cancer in 1956.