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.
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