Reid and his officers discussed trying to escape, but the winds were against them. The captain asked Dabney if he thought the British would respect the neutrality of the Portuguese harbor. The Royal Navy sloop Thais and brig Calypso had been patrolling near the Azores, and Dabney believed that their commanders were prudent. Judging by the size of the recent arrival, the visitor assumed she was the Calypso and told the Americans they had nothing to worry about. The brig anchored not far from the General Armstrong , and Dabney went ashore after suggesting Reid might move his ship under the guns of the harbor’s Portuguese fort, just to be safe. 3
The British ship, however, wasn’t the Calypso . Instead she was HM Brig Carnation , the van of a squadron under the command of Captain Robert Lloyd, sailing for Jamaica to join the invasion fleet for the assault on New Orleans.
Repulsing the First Attack
While the Carnation anchored, the squadron’s other two ships sailed into sight: HMS Plantagenet , a third-rate 74-gun ship-of-the-line, and HMS Rota , a 38-gun frigate. They remained outside the harbor. 4
As the sun began to set, Reid watched the British furiously work their signal flags. After several exchanges, with darkness setting in, the Carnation put out boats, and the Americans became suspicious. The moon dominated the horizon, and even after night fell the Americans could easily see that the British were preparing for something. Reid decided it would be wise to move under the fort’s guns. His men cleared the decks for action, then weighed anchor and put out their sweeps to move the ship closer to shore.
Reid’s suspicions were well founded. Captain Lloyd and the Plantagenet had visited the Azores earlier, at the beginning of September. The ship also had been in American waters, including on the Chesapeake, and Lloyd’s boats had launched an attack on Craney Island near Norfolk, Virginia. Charles Dabney heard that during the ship’s earlier visit to Fayal, Lloyd had “boasted that he had boats built expressly for cutting out American privateers, and he would destroy them whenever he found them.” 5
Observing the General Armstrong as she began to move, the British swung into action. The Carnation got under way, while four of her boats immediately made for the American privateer. Reid’s crew dropped anchor and prepared to repel boarders. As the anchor set, the Americans put out spring lines, so that they might pivot the schooner, and manned their guns. 6
At 2000 the British boats, with what appeared to be 100 to 120 men on board, approached the Americans. Captain Reid hailed them and asked their business, but they continued forward without a reply. He hailed again and warned them to keep away. The boats only appeared to pick up speed as they pulled toward the schooner. Reid made one last attempt to warn them off, and then ordered his men to open fire. Small-arms fire and a broadside from the schooner’s 9-pounders wreaked havoc on the small craft. The British returned fire but were quickly overwhelmed and began to retreat. In the brief engagement one of the privateer’s seamen, Burton Lloyd, was killed and her first lieutenant, Frederick Worth, wounded. Captain Reid estimated 20 casualties on the British side. 7
Reid and his men watched as the British retreated to the Carnation , which then sailed to join the larger ships of the squadron. In the light of the nearly full moon, the Americans saw the British ships put out more boats evidently in preparation for another attack. Reid responded by ordering his men to warp the schooner even closer to the fort. As they did so, resetting their anchor and springs, locals began to gather to watch the show.
Consul Dabney meanwhile sent his son Charles to the Portuguese authorities to insist they do something. The younger Dabney suggested to the governor that, because his garrison could not, or would not, stand up to a British assault, 32 American sailors who happened to be in port be allowed to reinforce the crew of the General Armstrong . The governor refused, saying that it would violate the neutrality of the harbor just as surely as a British attack, and instead dispatched an emissary to Captain Lloyd to insist that he respect that neutrality. 8
On board the General Armstrong , Reid and his men prepared to fend off another attack. About an hour after the first assault, they watched as the Carnation sailed into the harbor towing a large number of boats. Once inside, the boats maneuvered behind a small reef, about musket range from the Americans. The British brig remained under sail to ensure that the General Armstrong did not attempt to slip out of the harbor. 9
Bloody Fight for the Armstrong
The second attack began at midnight. A dozen British boats came on in close order and in single file. Reid’s men had spent the entire evening at their stations, and the General Armstrong was prepared. When all the boats were in range, the captain gave the order to fire and musket and cannon balls from the privateer smashed into the approaching craft. Sailors and marines in the boats returned fire with carronades, swivel guns, and small arms. Blasts from the privateer’s 42-pounder long gun, nicknamed “Long Tom,” however, staggered the British line. After a moment of disorder, the attackers recovered and raised three cheers. The boats then broke from the disciplined line of advance and, with tars pulling hard at their oars, raced for the American schooner, reaching her bow and starboard quarter. 10
As men in the boats grappled the General Armstrong ’s sides, the Americans heard British officers shout an order: “Board!” Stepping away from the big guns, the privateer’s crewmen took up any weapon at hand. With muskets, pistols, cutlasses, and boarding pikes they met the first group over the rail with a ferocious counterattack. Driven back into their boats, the British reorganized and made another attempt, but were once again cut down by the defenders.
The American crewmen at the bow, with Reid at their side, decimated their attackers as the bloody back and forth of assault and repulse continued. After 20 minutes, Reid received word from the division defending the stern of the ship that Second Lieutenant Alexander Williams had been killed and Third Lieutenant Robert Johnson wounded. Without leadership, the defenders there had begun to fall back.
Reid joined the aft division and rallied the men. After unleashing a fresh volley of musket fire, they charged and forced the British back over the stern rail. Forty minutes after the first shots had been fired, following wave after wave of boarding attempts, the attackers had been routed. As musket shots continued from the deck of the privateer, some of the British sailors and marines dove overboard and swam ashore to escape the bloodbath. Finally several of the boats limped away, others drifted across the harbor, and three remained lashed to the bow and stern of the General Armstrong , filled with the mangled bodies of the dead and wounded. 11
The Americans looked around their debris-strewn deck as quiet descended on Fayal Harbor. Long Tom had been dismounted in the fight, and several of the carriages of the smaller guns shattered. Wreckage lay all around them, both from the ship and in the form of six wounded sailors and the body of Lieutenant Williams. But the magnitude of the British loss was entirely different. With hundreds of men having participated in the attack, they reported suffering 36 sailors and marines killed and more than 80 wounded. Based on discussions with British officers after the battle, the Americans and Portuguese put the number closer to 120 dead. Reid would report two of his crew killed, seven wounded. 12
A Delayed Departure
Captain Reid’s attention immediately turned to the possibility of a third attack. He and his men were able to hoist Long Tom back into its mount and began to clean up the deck. Around 0300 word came from shore that Consul Dabney needed to speak with Reid, so he went ashore as his men continued preparations for a renewal of fighting.
Dabney had spoken with the governor, who had exchanged messages with Captain Lloyd. After the unexpected, embarrassing, and costly cutting-out attempt, Lloyd was determined to seize the General Armstrong . According to what Dabney was told, the British were even prepared to invest the town and destroy the garrison if the Portuguese did anything to help the Americans. Reid now realized he inevitably was going to lose his ship and further resistance would likely only result in more casualties among his men. He returned to the General Armstrong and ordered all the wounded to be carried off and the rest of his crew to begin moving their personal effects ashore.
With the day dawning, the Carnation sailed into the harbor and to within gun range of the privateer. The British brig opened up with a broadside from her 32-pounder carronades, and the Americans returned fire with Long Tom and what was left of their 9-pounders. When the brig hauled off after a few exchanges to repair some rigging, Reid took advantage of the respite and ordered his skeleton crew to scuttle the ship. The men holed the hull, climbed down into the last boat, and made for the nearby shore. A British boarding party took possession of the General Armstrong as she slowly sank and settled on the harbor bottom. The Americans had stripped the privateer, and her captors set the ship ablaze before retiring. 13
The British spent several days burying their dead and then tried to intimidate the Portuguese into turning over the privateer’s crewmen. The Thais and Calypso arrived and were loaded with the severely wounded for transport back to England. Captain Lloyd and his squadron finally set sail from Fayal for Jamaica and their rendezvous with the New Orleans invasion fleet. They arrived almost a week late, and the invasion force sailed for the bayous of Louisiana, only to be repulsed by forces under General Andrew Jackson and Master Commandant Daniel Paterson on 8 January 1815.
Some naval historians, including Theodore Roosevelt, as well as an 1880 U.S. Senate report have given Captain Reid and the crew of General Armstrong credit for buying the time needed for Jackson to complete his defensive preparations. Reportedly Jackson himself thanked Reid in the years following the war. Research into the British records of the engagement’s aftermath has shown, however, that the Plantagenet and her squadron may have arrived in time for the invasion fleet to leave on schedule, but the reason for its late departure remains elusive. Whether or not the Fayal Harbor fight affected the final battle of the War of 1812 in America, the daring defense of the General Armstrong remains one of the bloodiest and most dramatic examples of combat involving a privateer in American naval history. 14
2. Ibid, 495–96.
3. Charles W. Dabney to William L. Marcy, 21 May 1853, reprinted in Sam C. Reid Jr., ed., The Case of the Private Armed Brig of War Gen. Armstrong (New York: Banks, Gould, & Co, 1857), 19–21.
4. Kevin McCraine, “Naval Engagement at Fayal,” in Spencer Tucker, ed., The Encyclopedia of the War of 1812: A Political, Social, and Military History (Santa Barbara, CA: ABC-CLIO, 2012), 237.
5. C. Dabney to Marcy, 21 May 1853.
6. Reid to Jenkins and Havens, 4 October 1814.
7. John B. Dabney to James Monroe, 5 October 1814, American State Papers: Naval Affairs , vol. 1, 494.
8. J. Dabney to Monroe, 5 October 1814, C. Dabney to Marcy, 21 May 1853. Lloyd’s response, repeated in British histories of the battle, was that the boats were sent to determine the nature of the schooner and the Americans were the ones who attacked his innocent men. The pilot testified that he had told the British exactly who the Americans were and the Americans remained incredulous that four boats and more than 100 armed men, after dark, were anything but a cutting-out expedition. “The Case of the Private Armed Brig,” 18–22.
9. Reid to Jenkins and Havens, 4 October 1814.
10. J. Dabney to Monroe, 5 October 1814; Reid to Jenkins and Havens, 4 October 1814.
11. Reid to Jenkins and Havens, 4 October 1814.
12. Ibid. J. Dabney to Monroe, 5 October 1814. Reid Jr., The Case of the . . . Gen. Armstrong , x.
13. Reid to Jenkins and Havens, 4 October 1814.
14. Theodore Roosevelt, The Naval War of 1812 , Part 2 (New York: GP Putnam & Sons, 1888). John Van Duyn Southworth, War At Sea: The Age of Sails (New York: Twayne Publishing, 1968). Research casting doubt on the Fayal delay’s impact on New Orleans in Bob Rowen, “American Privateers in the War of 1812,” New York Military Affairs Symposium Paper, 2006, http://bobrowen.com/nymas/warof1812paper/paperrevised2006.html  .