Riders had been "literally riddled by the murderous fire from ambush." He called Gen. Wood and Col. Roosevelt "dandies" and noted: "It is due to them largely that the rough riders came home in better physical condition than most of the volunteers. Teddy hustled about and saw that food reached us." In October 1898, the New York World published an article titled, "Dudley S. Dean, Twice a Hero," which told of his exploits on the gridiron and at the Battle of San Juan Hill:"Dudley S. Dean ... is, as his friends express it, twice a hero. When Col. Roosevelt organized his regiment of Rough Riders, Mr. Dean was one of the first to enlist. He served throughout the campaign with distinction, and was in the thin brown line that charged up San Juan Hill. But his run at Springfield Nov. 22, 1890, when Harvard defeated Yale, is what endears him particularly to Harvard football men and the football world in general. On that occasion Dean ran through the entire Yale team for ninety yards and scored a goal." During World War II, Dean was a lieutenant colonel in the U.S. Army Air Forces and was the executive producer of the play "Winged Victory," which ran from November 1943 to May 1944. The play was intended as a morale booster and fundraiser for the Army Emergency Relief Fund. The play depicted both the training and work of airmen. Business career After graduating from Harvard, Dudley worked for the El Paso and Western Railroad. He was also a reporter and columnist for the New York World and Boston Globe for a time. Dean was involved for most of his professional career in the mining business, and the companies with which he was associated had extensive land, lumber and mineral holdings in the Gogebic Range of northern Michigan. He was affiliated with the Keweenaw Land Association, Ltd. for more than 50 years. In 1920, Dean was the treasurer of the Keweenaw Land Association, at which time the company owned of timber and mineral lands in the copper belt of Michigan's Upper Peninsula. Dean eventually became the company's president. He was also the treasurer of the Newport Land Company. Family and friends Dudley's son, John H. Dean, also played football for Harvard and was captain of the 1933 team. Dudley became friends with Joseph P. Kennedy as the two men spent summers together in