Born in Dublin, Ireland, Reginald Webster's family emigrated to the United States when he was a small boy.
Pursuing a career in business, he was president of precision parts manufacturer Standard-Thomson Corp. of Waltham, Massachusetts.
With the future Hall of Fame trainer, Webster had his best successes in American racing when in 1966 they won the Belmont Stakes.
His Irish-bred colt Martial, trained by legendary Irish horseman Paddy Prendergast, won the 1960 2,000 Guineas at England's Newmarket Racecourse making Webster one of only a few Americans to ever win both an American Classic and a British Classic race.
He was living in Palm Beach, Florida when he died at age eighty-five of heart failure.