Naval battle off Halifax The Battle off Halifax took place on 28 May 1782 during the American Revolutionary War . It involved the American privateer " Jack " and the 14 - gun Royal Naval brig off Halifax , Nova Scotia . Captain John Ropes commanded " Jack " , and Lieutenant John Crymes commanded " Observer " . The battle was " a long and severe engagement . " Background . During the American Revolution , Americans regularly attacked Nova Scotia by land and sea . American privateers devastated the maritime economy by raiding many of the coastal communities , such as the numerous raids on Liverpool and on Annapolis Royal . The engagement between " Jack " and " Observer " was one of several in the region . On 10 July 1780 , the British privateer brig " Resolution " ( 16 guns ) under the command of Thomas Ross engaged the American privateer " Viper " ( 22 guns and 130 men ) off Halifax at Sambro Light . In what one observer described as “ one of the bloodiest battles in the history of privateering ” , the two privateers began a “ severe engagement ” during which both pounded each other with cannon fire for about 90 minutes . The engagement resulted in the death of possibly 18 British and 33 American sailors . " Jack " herself was involved in a previous naval engagement . " Jack " ( or " Saucy Jack " ) was originally a Massachusetts privateer commissioned in September 1779 . After three successful cruises in which she captured a number of prizes , and captured her in July 1780 in the St . Lawrence River . The British took " Jack " into the Quebec Provincial Marine , though she was commissioned out of Nova Scotia . She then served as a patrol vessel for the fisheries and the St . Lawrence River . In an engagement off Cape Breton with two French frigates at Spanish River , near Cape Breton Island in 1781 two French frigates captured her . They took " Jack " back to Boston , where her previous owners purchased her and sent her to sea again as a privateer . " Observer " was herself a former Massachusetts privateer , originally built as a merchantman , the " Amsterdam " , which captured on 19 October 1781 . The British sent " Amsterdam " into Halifax to be condemned as a prize , where the Royal Navy bought her . Battle . " Observer " was returning to Halifax , having rescued ten crew members of HMS " Blonde " after " Blonde " wrecked on Seal Island off Cape Sable Island . On 28 May 1782 , as " Observer " arrived at the Sambro Island Light near the mouth of Halifax Harbour , " Jack " approached her . When " Jack " discovered her quarry was a British naval vessel , the Americans tried to escape . " Observer " chased " Jack " for two hours before catching her . The ships were evenly matched . The British immediately killed the American captain John Ropes as a result of the cannon fire . Both ships had numerous holes shot through their sails , and the British sailors attempted to climb the rigging of their ship in an effort to board the American privateer . The Americans repulsed this initial boarding attempt , but the British were ultimately successful . " Jack " struck her colours on the afternoon of 29 May . Aftermath . American privateers remained a threat to Nova Scotian ports for the rest of the war . The following month , after a failed attempt raid Chester , Nova Scotia , American privateers struck again in the Raid on Lunenburg in 1782 . References . Secondary Sources Primary Sources