Born in Trail, British Columbia, he attended St. Thomas More Collegiate in Burnaby.
He attended St. Francis Xavier University in Antigonish, Nova Scotia, where he also played football.
His Ph.D. thesis was entitled, "Maritime communities in pre-plague England: Winchelsea and the Cinque Ports".
[2] While at Fordham, Sylvester met his future wife, Allyson Larkin, who was in the same program.
At the time of his hiring he also served as the vice-chair of the Association of Catholic Colleges and Universities of Canada.