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Built at Liverpool in 1798 by a consortium of Liverpool, NS investors, the 130 ton, full-rigged ship (three masts, all carrying square rigging) Charles Mary Wentworth began her career as a privateer in August 1798. Carrying 16 cannon and a crew numbering over eighty, this was one of the largest and most formidable privateers to sail from Nova Scotia.
Her first three cruises into the Caribbean against the French and Spanish proved highly successful. Enough lucrative prizes were taken to give both owners and crew members a sizeable income. Prompted by this record of success, the Wentworth (named after the son of Nova Scotia's Lt. Governor, Sir John Wentworth) returned to sea again in November 1799, under the command of Captain Thomas Parker, a resident of Liverpool. On board were a crew mostly recruited from Nova Scotia's "south shore." Included in that contingent were six to eight black sailors, most likely people who had come to Nova Scotia during the Loyalist exodus from the new United States, some fifteen years earlier.
Hunting in tandem with two other Nova Scotia privateers off the coast of Venezuela and later in waters off Guadeloupe and Puerto Rico, the Wentworth had a lively series of encounters, especially those involving First Lieutenant Enos Collins (who, later in life, became enormously successful as a Halifax merchant). But years spent in waters infested with wood-boring worms had made the Wentworth leaky and slow, thereby reducing her ability to chase after prizes. In the end, only one capture was made on that fourth cruise, meaning little income for the crew and for the owners, a major financial loss. The next time the Wentworth put to sea it would be as an ordinary merchantman, retired from her days as a privateer.
Date: 1799-1800
Reference: Royal Nova Scotia Historical Society Nova Scotia Archives MG 20 volume 215 number 10
Nova Scotia Archives — https://archives.novascotia.ca/privateers/archives/?ID=16
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