He was educated at Rockville Academy, Emerson Institute, St. John's College, Annapolis, Maryland, and Washington and Lee University.
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Prettyman was born on April 7, 1860, in Brookeville, Maryland, the son of Elijah Barrett and Lydia Forrest Prettyman.
After spending time at Columbia University and the Nicholas School in Buffalo, New York, Prettyman moved to Hamilton College in Clinton, New York to teach physical education and coach.
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Prettyman was the head coach for 1936 United States Hockey Team in the Winter Olympics in Garmisch-Partenkirchen, Germany.