One of Cobourg’s most famous and colourful skippers was Captain Rooney or “Little Dan”as he was known locally . Born in 1864, in the area of Cobourg known as “Corktown“, Little Dan came from a family of sailors and vessel owners.
When he was fifteen, he himself went sailing on the schooner Hannah Butler of Cobourg, and at the age of 21 commanded his first schooner.
Little Dan was reputed to have accomplished many sailing feats including being in charge of two ships at once. In a deal with the Richardsons, Kingston grain merchants, Little Dan purchased a share in the Charlie Marshall, a three-masted schooner of 219 tons. The Richardsons then hired him to captain the Sophie J. Luff, another three master of 253 tons. The agreement provided that the Captain would sail both vessels and receive two separate master’s wages plus his share of the earnings from the Charlie Marshall.
Typically, Rooney would sail the Charlie Marshall from Cobourg to Oswego, New York, to load coal. While the coal was being loaded, he would travel by steamer to Kingston and sail the Luff with her cargo to Charlotte (Rochester). As the Luff was unloaded, he would take the train to Oswego, run the Charlie Marshall back across the lake to Cobourg and catch the ferry to Charlotte where the Luff waited for him to take charge of her again. Rooney made such a profit for everyone concerned that he was able to convince the Richardsons to sell him the remaining shares in the Charlie Marshall.