Island History: Pirates in Our Region

Island History: Pirates in Our Region

by Pierce Rafferty

On Block Island

On July 12, 1690, the residents of Block Island were alarmed when a small fleet—consisting of one bark, one ketch, two sloops and smaller craft—appeared off their coast. Although the vessels were flying English colors, there was no certainty of their allegiance to the English crown. King William’s War (1688-1697) had broken out in North America two years earlier pitting the English against the French (New England against New France), a smaller part of the Nine Years’ War raging in Europe. Pirates and privateers were frequenting the waters outside and within Long Island Sound; these marauders were masters at masquerading their true loyalties, when they bothered to have them.

After the fleet anchored outside the harbor, a flat-bottomed sailboat carried a landing party to shore, but only one man stepped out. He was met by a large, anxious crowd, including armed soldiers, who demanded to know his party’s intentions: Where did they come from? Where were they going? What was the name of their commander?

The solo man identified himself as William Trimming, an Englishman, and answered each question forthrightly. He as-sured the assembled men and women that he and his compatriots were friends, not foes. He told them that his fleet’s commander was George Asten, an English privateer well known to all in the crowd for his successes against the French and Spanish. He stated that they were coming from Jamaica, headed to Newport and needed a pilot boat to lead them into the harbor, where they could purchase supplies and secure water be-fore proceeding. Trimming provided enough details about his commander, Captain Asten, that the islanders were assured. They allowed the landing party to return to the fleet so that it could be guided safely into the harbor.

The voluble Trimming had neglected to mention that he was the only Englishman aboard any of the vessels; all the rest of his mates were French pirates—with a few Spanish and mestizos thrown in. He also left out the detail that their French captain had a good deal of experience in plundering.

Rejoining his fleet, Trimming summoned a pilot boat. The moment its crew stepped aboard, they were seized and thrown into the hold for questioning. The pirates needed to determine the relative strength of the defending forces at Newport and Block Island before deciding which site to plunder. Because the Block Islanders had swallowed Trimming’s lies hook, line and sinker, that site was chosen as the easier prey.

Three boats brought about 150 armed men to shore. Upon landing, they pulled out their hidden weapons, disarmed the soldiers, and quickly took control. The penalty for resistance, they announced, was death. The gullible islanders were shocked to discover that Englishman Trimming had betrayed them, for he had played his role of decoy perfectly. Foreign pirates (technically “privateers” under license to France) were now in perfect position to loot and terrorize.

After herding and locking the men, women and children into a large stone house, the pirates began to strip Block Is-land of its valuables. The occupation lasted a week, during which time the invaders pillaged most houses and farms on the island. There were cruel beatings, whippings, and several killings carried out as the marauders tried to discover the location of any hidden wealth. The vandals slaughtered cattle and other livestock both for food and to deprive the islanders of property and provisions.

After word reached the mainland that French pirates had seized Block Island, local citizens and guards lit beacon fires signaling alarm along the shore from Pawcatuck Point, Connecticut (then part of Rhode Island), to Seaconnet, Rhode Island (then part of Massachusetts). These bonfires helped inform the pirates’ decisions to leave Block Island and to by-pass a forewarned Newport, a city with a large population and fortifications.

The pirates chose instead to attack New London, suspect-ing that its citizenry would be less aware that they were in the neighborhood. But as their fleet, once again flying English colors, passed Watch Hill and Napatree Point, residents of Stonington caught sight of it. Those on shore had enough concern to dispatch a cautionary warning to New London by messenger on horseback.
The pirate fleet sailed around the south side of Fishers Is-land to mask their approach to New London. As they rounded Race Point, Trimming’s boat, carrying a small number of men, broke off from the rest of the fleet and made a landing on Fishers Island, likely at West Harbor. The other pirate vessels continued on toward New London.

On Fishers Island

Concerned residents of Stonington, seeing the single boat peel off, organized a force of 17 men to sail to Fishers Island, where they planned to make inquiries and intervene if need-ed. They landed at a different location than the pirates and reached the only house on the island (likely located near to-day’s ballfield) without being seen. During this period there were only a few tenant farmers and Indian farm laborers liv-ing and working on the island; Fitz-John Winthrop, the New London-based owner of the Island, was away commanding English forces against the French, and preparing to invade Canada. Preoccupied by a distant campaign, Winthrop would have been shocked to know that the enemy had already land-ed on his island and was about to attempt the sacking of his hometown. As the Stonington group approached the house, William Trimming emerged from inside and greeted them in a casual and friendly manner. According to witnesses, he kept his gun hidden behind his back. When queried as to what he and his men were doing on Fishers Island, Trimming replied that they had recently been “cast away” (shipwrecked), a blatant lie that was immediately apparent to the Stonington men who had just witnessed his approach to the harbor. With his men’s fear palpably rising, the Stonington group’s leader tried to defuse the situation. He addressed the pirates, saying “If you are friends, lay down your guns, and come behind us.” Before the pirates could answer, a man in the Stonington group panicked, aimed his pistol, and shot Trimming dead. The other pirates scattered and fought their way back to their boat. They managed to rejoin the larger fleet, suffering the loss of only one additional man during the skirmish.

After the pirates made their escape, an Indian farm laborer scalped Trimming’s corpse and took the trophy to the main-land as a gift for the English. The Stonington man who had killed Trimming came under criticism for firing prematurely, but many had a sense that poetic justice had been served. Samuel Niles, a chronicler of the encounter, expressed this sentiment: “Thus he that delighted in false hood in life died with a lie in his mouth; and received, it seems, the just reward of his perfidious, villainous, and multiplied treacheries.”

New London

On July 17, 1690, the pirate fleet began its raid on New London. Flying English colors as they entered the harbor, the fleet sailed past the town and anchored upriver within shout-ing distance of shore at Mamacoke Point, across from today’s Naval Submarine Base.
There they repeated some of the tactics they’d used at Block Island, professing friendship, explaining that they had come from Jamaica, etc. The crowd on shore, already numbering about 150, was growing; it included many who had come in from the countryside. Seeing no advantage in their location, the French pirates changed course and sailed back to New London, making anchorage next to a docked ship in the town. From that position, the pirates called out several invitations for those ashore to come aboard, but these went unanswered. Had they been accepted, the taking of hostages would have almost certainly resulted, likely followed by threats, ransom demands and attempted pillaging.

As the ranks of the shore defenders continued to swell, exceeding 400 by one count, the prospect of a successful pirate attack grew dimmer. With the wind turning against them, it was now or never. The French flag was suddenly raised, apparently a triggering signal, for all the ships began to fire a coordinated volley shoreward. Their fusillade was met by counter volleys from land-based cannon. The pirate fleet, in a strategically untenable position, retreated to the middle of the river under power of oars before pulling to the mouth of the harbor, beyond cannon range, to anchor for the night. They were relatively unscathed but had achieved none of their goals. One observer scornfully contrasted the fleet’s “formidable and swaggering” entrance into the harbor with their “sneaking and shameful” exit. A large guard of 350 men kept watch from shore throughout the night to prevent any new incursion or attack.

Back on Fishers Island

The next day, the three smaller ships from the pirate fleet sailed to Fishers Island and anchored off its west end between the hammocks and the main harbor. The 50-ton bark, the largest vessel, ventured out into the Sound and captured a sloop, then returned and anchored with the others. Fishers Island was theirs for the taking, as all the farm workers and Indian laborers had fled after the skirmish between Trimming and the Stonington men.

A letter dated August 11, 1690, from Wait Winthrop to his brother Fitz-John, reveals what little is known of the pirates’ activities on the Island: “The pirates lay in the harbor at ye island two or three days and burnt the house; and what mischeife else I know not certainly yet, but tis said a great deale.” The tone of the letter is remarkably dispassionate, given that the house was the only one on the Island and Fitz-John Winthrop was its owner.

The fire on Fishers Island was quite evident from Stoning-ton, triggering concern among the farm hands who had fled about the availability of future housing on Fishers Island (a concern that remains relevant more than 325 years later). In his letter, Wait Winthrop assured Fitz-John that he had convinced the men to return again to the island farm, promising that “[they] shall have a house before winter if it may be; in the mean time have sent to the Indians at the farme to help them about a wigwam while they secure the corn and hay.” Until winter set in, wigwams would have to suffice.

After departing Long Island Sound, the pirates’ largest vessel, the 50-ton bark, was routed in an engagement with a heavily armed Rhode Island sloop off Block Island. The captain of one of the pirate ships and 13 crew members were killed. Following the battle, the rest of the fleet made their escape under cover of darkness. Although saddened by this successful flight, Block Islanders and all in the region must have gotten great pleasure from accounts of the French pirate captain’s final moments.

During the battle, he brashly shouted insults at the opposing captain, promising that the English vessel would soon be boarded. To accentuate his swaggering display, he began drinking a bottle of wine as he stood fully exposed on deck. He was still swigging his wine, and presumably still shouting, when an English musket ball pierced his neck, ending his insults forever.