Phelan, who sailed Dragon-class yachts, was a past Commodore of the RCYC, president of the CYA from 1961-1963 and again in 1990-91, and was presented the 1986 Sail Canada Rolex Sailor of the year award for his merger of two rival Canadian bids for the 26th America's Cup, when he funded a merger between them for $14 million.