HARRY “COTTON” HENNING served as crew chief for four Indianapolis 500 winners, his first being with Peter DePaolo and his 500 record run of 101.13 miles per hour for Fred and Augie Duesenberg in 1925. He also was crew chief for all three wins by car owner Mike Boyle in 1934, 1939, and 1940. The drivers were Bill Cummings in 1934 and Wilbur Shaw driving the famed Boyle Maserati in 1939 and 1940. For many years, Henning was the full-time general manager for the Chicago-owned Boyle Racing team, which was headquartered in Indianapolis. By far the most dominant team from the late 1920s through the mid-1940s, Boyle typically fielded three or four cars under Henning’s watch for drivers who included Ted Horn, Billy Arnold, Louis Meyer, Mauri Rose, Lou Moore, Babe Stapp, Chet Miller, Shaw, Cummings, and DePaolo. Henning-prepared cars won the Indianapolis 500 pole position in 1932 with Moore, in 1933 with Cummings, and in 1947 with Horn. After winning in 1939 and 1940 with Shaw, he almost won again in 1941 until Shaw was eliminated by an accident while leading at the three-quarter mark. After World War II, Henning-prepared cars had two third-place finishes and a fourth-place finish with Ted Horn driving the Maserati from 1946 through 1948.