In 1906 Hugh bough his first vessel the 60 ton Castletown Schooner "JCR" and put his brother William in as captain . William loaded a cargo of slate from Porthmadog for Waterford but when Hugh reached Abersoch in the SARAH LATHAM the first news he was given was that the JCR had been wrecked on the Splaugh rocks as she entered Rosslare Harbour. Fortunately no lives were lost but with no insurance on the vessel Hugh lost all of his savings.
built Castletown 1865
JCR at Castletown National Maritime Museum photograph