Winner was born in Philadelphia and spent his life here with the exception of a visit to Charleston in 1848. He does not appear in the student records of the Pennsylvania Academy of the Fine Arts but is listed as an Associate artist in 1847 and 1860. His exhibition record at the Academy is remarkable for its longevity (1836 to 1881) and for the range of subjects which it reveals. Portraits, landscapes, genre (The Village Letter Carrier, Youthful Sports), history (Incident in the Storming of Quebec) religion (Elijah and the Angel), literary illustration (Coriolanus) and cooperative efforts (Sea Piece; figures by Winner, sea by G. R. Bonfield) all played a part in his repertoire. He also exhibited at the Boston Athenaeum, the Apollo Association, the American Art Union, and the National Academy of Design.