One of the original “Dallas Nine” in 1932, Winn studied with Taos artist Oscar Berninghaus, at Washington University in Saint Louis, and at the Academie Julian in Paris. He assisted on the Texas history mural in the Hall of State for the 1936 Centennial Exposition in Dallas. In 1946 his design was chosen for the U.S. commemorative stamp for Texas statehood. In addition to artistic pursuits, Winn patented several inventions. He lectured on architectural subjects at Rice Institute, Princeton University, Texas A&M, and other institutions. He exhibited at the State Fair of Texas and the Dallas Allied Arts shows in the early 1930s before turning almost exclusively to mural painting and large-scale public works, including his murals at the Texas Memorial at Gonzales. Haymakers hung in the U. S. Embassy in Bucharest, Hungary, from 1995 to 1998.