Dudley Dean Dudley S . Dean ( ca . 1872 – September 25 , 1950 ) was an All - American football quarterback for Harvard University . He played quarterback for Harvard from 1888 - 1890 and was selected as an All - American in 1890 . Dean also fought with the Rough Riders at the Battle of San Juan Hill during the Spanish – American War . College athlete at Harvard . A native of Lake Village , New Hampshire , Dean enrolled at Harvard University . While at Harvard , Dean was the quarterback for Harvard ' s varsity football team . He became famous for his role in Harvard ' s November 1890 football victory over Yale — the first since the schools first met in 1875 . A newspaper account of the game described a touchdown run from midfield by Dean . Yale had the ball at midfield when Dean broke through past Hall of Famer Pudge Heffelfinger and batted the ball out of the hands of the Yale quarterback . The report noted : " The ball bounded beautifully for the now famous ' Dud . ' He caught it as it came up saying , ' Now Dud ' s your chance . ' On the run he was past the Yale backs . . . and had a clear field to Yale ' s unprotected goal . " The report called Dean the " hero of the day " and concluded as follows : " After all has been said , however , about individual players , and a vast deal might be said , the last word should be devoted to Dudley Dean . If the Harvard victory can be ascribed to one man more than any other , that man is Dean . His tackling and breaking through were unsurpassed . At the end of the 1890 season , Dean was selected as the quarterback on the All - American football team . Dean also played shortstop and second base for the Harvard baseball team and was captain of that team in 1891 . His skills as a baseball player were such that he traveled with Albert Spalding ' s professional baseball tour of England and was paid £4 a week plus expenses . Military service . During the Spanish American War , Dudley enlisted and served with the Rough Riders . In July 1898 , after the Battle of San Juan Hill , Dean was one of five members of the regiment mentioned by Theodore Roosevelt for bravery on the battlefield . In his book , " The Rough riders , a history of the First United States volunteer cavalry , " Roosevelt named Dean as " one of the men whom I noticed as leading in the charges and always being nearest the enemy . " Upon his return , Dudley told how the Rough 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 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 Cohasset , Massachusetts . In 1922 , Dudley led an unsuccessful campaign to have Kennedy admitted to the Cohasset Golf Club , and several of his letters lobbying for Kennedy ' s admission were published in the book , " The Fitzgeralds and the Kennedys " , by Doris Kearns Goodwin . Dean died at his home in Cohasset at age 79 .