David Mitchell writes of the notorious buccaneer Bartholemew Sharp that he was last heard of in 1688 serving as 'Governor' of Snake Island or Anguilla. He writes that Sharp presided over a lawless population, selling dubious commissions freely to old friends, and lighting his pipe with summonses for his arrest. This is a charming and romantic story, but there is not a shred evidence to support it.
Sharp may have visited Anguilla, or at his trial he may have called himself commander of Anguilla. Not one official document exists indicating that the Governor-in-Chief or any other authority ever appointed him to any position in the island. There is no indication in the available records that he ever resided on Anguilla or was acknowledged by the Anguillians as their commander.
Snake Island was not a common name for Anguilla during the seventeenth century. That name does later occasionally appear in uninformed writing, apparently as a free translation of the name Anguilla. In the year 1688, it was Abraham Howell, not Bartholomew Sharp, who was deputy governor of Anguilla. In that year Howell led his hardy followers in fighting off Spanish, French and Irish marauders on Anguilla, as described earlier. It was only in the eighteenth century that map-makers and armchair commentators began to take the liberty of translating the name of Anguilla as Snake Island.
The association of piracy and buccaneering with Anguilla in the minds of writers and officials begins early. In the historical records dating back to the seventeenth century, Anguilla begins to develop a wide but undeserved reputation as being a haunt of pirates and buccaneers.
The so-called 'Classic Age of Piracy' ran from about 1714 to about 1724. These were the years that saw the activities of Edward Teach otherwise known as Blackbeard, Bartholemew Roberts, and the female pirates Mary Read and Ann Bonny who at their trial were able to 'plead their stomachs.' Slightly earlier were Pier le Grand, Francois Lollonais, Henry Morgan, Bartholemew Sharp, and William Dampier. The period of the 'Pirate Round' was even earlier. The pirate round lasted from about 1693 to about 1700 when such characters as Thomas Tew and William Kidd flourished. These Roundsmen would start their cruise in New York, Bermuda or Nassau. They would round the Cape of Good Hope and commence their search for rich Mughal shipping in the Indian Ocean north of Madagascar.
Some of these characters touched at Anguilla. Space permits a mention of only those of them and of their activities that tell us something of the life and character of the Anguillians of this period. We shall see that Anguilla was affected to a certain extent by some of the buccaneers and pirates we have just named.
It is in the year 1672 that Anguilla first appears, quite innocently, associated with the unlawful seizing of a ship. That seizure was made by Sir Charles Wheeler (spelled Wheler in the correspondence), the new Governor-in-Chief of the Leeward Islands. He was then on a familiarization tour of the islands of his colony. Anguilla's connection with the incident is only accidental and peripheral. Nevertheless, that connection is the beginning of a series of incidents that conspired, over the years, to transfer to the island a sort of guilt by association. It culminated in the early eighteenth century in outright accusations of piracy and smuggling.
On 10 May 1672, a petition by one John Knight and other merchants against Wheeler’s seizing of their ship William and Nicholas was read in London by the Committee for Foreign Plantations (see illus 1).
1. The commencement of John Knight’s 1672 petition. CO.1/28. (UK National Archives®)
The petition revealed the following chain of events. The ship was returning to England from the West Indies, laden with logwood. It was forced by bad weather to put into Anguilla. There it was found to be so leaky that the owners, being then at Barbados, hired another sloop, the Swan, to go to Anguilla and to take her cargo to London. Before the Swan's arrival at Anguilla, Wheeler seized the ship and condemned it and its cargo. His accusation was that the logwood was illegally cut at Belize in Central America in breach of a treaty with Spain. England was then at peace with Spain. Wheeler was mistaken, however. It was illegal for Englishmen to take logwood from Spanish ships, but the trade in logwood was not prohibited.
That same day that the petition was read, the Council recommended to the King that the ship and her cargo be released. Wheeler’s action was deemed unjustified and he was recalled to London and replaced as Governor-in-Chief by Col William Stapleton, deputy governor of Montserrat. The Privy Council instructed Stapleton immediately to restore to the owners the ship and its cargo. On 13 July, Stapleton replied that he delivered the logwood to the owners. The ship meanwhile, he reported, sank at anchor in The Road.
The ‘Road’ refers to Road Bay, Sandy Ground, Anguilla’s main harbour then as now. Road Bay lies on the north coast, partially encircled on the north, south and east by a low hill. The village on the north and east of this hill is called ‘North Hill’ village. The village to the south is called ‘South Hill’ village. Since they are both on the north coast, the reason for this nomenclature has long mystified visitors. The explanation is not apparent to anyone who is not a sailor. When you sail from the west eastwards into Road Bay, and anchor at your mooring, the cliff to the south of you is naturally referred to as South Hill. The hillside to the north of you is equally naturally named North Hill. It is only when you are on a ship anchored in Road Bay that the distinction of these two north coast villages as South Hill and North Hill becomes apparent.
The unfortunate Wheeler was doing what he perceived to be his duty. His commission as Governor-in-Chief instructed him to take steps to reduce the depredations of the Leeward Island colonists and traders on the Spanish Main. In consequence, he arrested the ship which he suspected was laden with logwood illegally obtained in Spanish territory. He was also, of course, at the same time trying to ensure himself an income. Senior government officers in the colony of the Leeward Islands at that period received no salary. They were expected to live off the ‘fruits of office’. Wheeler was entitled, as Governor-in-Chief and Judge of the Court of Admiralty, to at least part of the proceeds of any vessel he condemned for piracy or as prize of war. He appears to have made one of two mistakes. Either he was wrong to believe that the ship was transporting illegally obtained logwood from Belize. Or, which is more likely, the owners of the William and Nicholas had more important friends at the Court of St James than he did. With this relatively innocent involvement, Anguilla’s name begins its centuries long association in the minds of the colonial authorities with piracy and buccaneering.
Ten years later, Anguilla crops up again in a report about piracy. In a dispatch of 1683, Governor Stapleton complained about the Danish Governor Adolph Esmit of St Thomas. He reported that Esmit harboured fugitives who preyed on the merchants of the Leeward Islands. The Virgin Islands, including Crab Island, were an important source of timber for building purposes. Governor Esmit provided a sanctuary for runaway servants, black and white, and for the seamen and debtors who ran away to the Virgin Islands.
Stapleton reported that Esmit allowed pirates to bring in to port in St Thomas a sloop owned by Thomas Biss of Nevis. Esmit refused to release either the ship or its crew on the ground that it was contrary to the law and custom of St Thomas. As Thomas Biss said in his deposition which accompanied the dispatch, Esmit invented excuses for not returning his ship. First, he said that she was found derelict at sea. Then, he claimed that she was taken by privateers from other privateers. Then, he changed his story yet again and, more damaging to Anguilla’s reputation, claimed that when she came in to port in St Thomas she showed a clearance certificate from the deputy governor of Anguilla authorising her to acquire timber.
Esmit’s explanation was that, having seen this clearance, he allowed them to take on board wood and water and released them after fourteen days. As they did not set sail immediately, he became suspicious. He then made further investigation of them. It was only then, he wrote, that he discovered they were selling goods at prices far below their market value. He claimed he then made a thorough investigation and discovered that they possessed no commission or papers for the goods. He, therefore, adjudged them to be pirates. Whereupon, they fled from the island, and the sloop became forfeited to the King of Denmark. This is an interesting story of the dangers of maritime trade between Anguilla and the neighbouring islands. There is no record if Thomas Biss ever got his boat back.
This is the earliest time that the allegation arose that the deputy governor of Anguilla supplemented his income by selling false customs clearances. As we shall see, it was a spurious claim that was to reappear from time to time. It was a libel on Abraham Howell. From the testimony in this dispatch, it is evident that even Esmit realised that the Anguilla clearance was forged, and that it was not prepared by the deputy governor.
Anguilla next appears connected to piracy in the dispatches of the Governors-in-Chief to the Lords of Trade in 1699, when William Kidd attempted to land here. The Council for Nevis wrote on 18 May to the Secretary to the Committee, William Blathwayt. They reported that about twenty days previously, Kidd touched at Anguilla, but that the islanders refused him assistance. He left for St Thomas where he was similarly refused provisions, though he anchored off the harbour for three days. The Nevis Council report clearly exonerates the Anguillians of any charge of providing safe harbour for Kidd, as was subsequently alleged.
While he was incarcerated in London awaiting execution, Kidd wrote a statement about his travels and troubles (see illus 2). While he recorded that his boat touched at Anguilla, it does not appear that he and his men actually landed there. He did state that he first learned from the Anguillians that he was the subject of an English proclamation declaring him to be a pirate. It is clear from this that when he arrived in Anguilla, the Anguillians knew that he was a pirate and did not give him any help. However, the mere mention of pirates touching at Anguilla was to cause some of the stigma associated with the pirate in question to rub off on Anguilla. These allegations of visits by pirates were to affect the island’s reputation in the years to come.
2. Kidd hanging in chains after his execution.
The next blow to Anguilla's good name occurred in the year 1701. Governor Codrington Jr wrote to the Committee for Trade that the men of Anguilla were perfect outlaws (see illus 3). He claimed that they worked for the Danes and Dutch and that it was impossible for him to prevent it. In addition, he said, Anguilla served as an intermediate mart or repository for prohibited goods from St Thomas and Curacao. By this, he meant that the Dutch and Danes used Anguilla to warehouse some of the prohibited goods that they traded with the English Islands contrary to the Navigation Acts.
3. An extract from Codrington’s dispatch of 10 November 1701 to the Council describing corruption in Anguilla: CO.153/7. (UK National Archives®)
He suggested that the Anguillian merchants and traders were working with the Danes and Dutch whose freeports, merchants and shipping engaged in prohibited trade between the English colonies and foreigners. If this is true, then it shows that the profession of smuggling has an ancient pedigree in Anguilla. However, there is no evidence that during the first half of the eighteenth century Anguilla acted as any sort of intermediate repository for smuggled goods. This was an activity that the neighbouring islands of St Bartholomew and St Eustatius specialised in. Anguilla was too poor ever to have a warehouse on the beach. Any storing of goods in Anguilla at that time was in the open, on the beach, exposed to sun and rain.
Due note was taken in London of Codrington's accusation. The following year, William Popple, Secretary to the Commissioners for Trade and Foreign Plantations, wrote a memo to John Sampson of HM Customs to acquaint him with the details of the illegal trade allegedly being carried on by the people of Anguilla, and of the corruption in the customs department of the Leeward Islands, as reported by Governor Codrington. The report was duly circulated, and another black mark entered in Anguilla's record.
It is this illegal trade of smuggling, rather than any connection with buccaneers or pirates, that is more probably than not the origin of the description of Anguilla in the late seventeenth and early eighteenth centuries as a haven for outlaws. From the earliest years, the Anguillians built or bought sea-going boats and conducted trade between the islands. At any other time than during the regime of the Navigation Acts, they would have earned the description of being industrious and hard-working. There is no evidence that any Anguillian was ever charged with, far less convicted of, the offence of piracy.
In 1706, a more serious accusation appeared in a dispatch from Richard Oglethorp to the Committee for Foreign Plantations. He accused deputy governor George Leonard of being indebted to Captain Kidd's colleague, Tempest Rogers. He charged Leonard with the offence of dealing knowingly with the goods of Captain Kidd. No further detail is forthcoming. No consequences appear in the record. Leonard was not investigated. He continued in his appointment as deputy governor. Oglethorp provided no evidence to substantiate his vague charge against the deputy governor. We can hope that the authorities realised that it was a false libel. Interestingly, Richard Oglethorp subsequently married Johanna Rogers the widow of Tempest Rogers. He spent some time in Antigua between 1709 and 1712 before settling down in Charleston, South Carolina where he died in 1719. Heaven alone knows what tensions lay behind that charge he made against George Leonard in 1706.
Traders from other islands were not reluctant when caught contravening the Navigation Acts to produce forged clearances purporting to be issued by the deputy governor of Anguilla. We know they were forged. There is a record of a 1764 complaint by the Surveyor General of the Customs of finding “forged certificates for Salem under Anguilla clearances.”
In a dispatch to London the following year, 1765, Governor-in-Chief Sir George Thomas informed the Committee that there was no truth in the charge. He wrote that there was no great illicit trade to his knowledge in any of his islands. In St Eustatius, he explained, an Englishman by the name of Claxton possessed a number of forged clearances that appeared to be issued by the deputy governor of Anguilla. With these forged customs clearances, Claxton purchased large quantities of French sugar, rum and molasses at St Eustatius and St Croix. He then clandestinely imported them into North America as if they came from Anguilla. Deputy governor Benjamin Gumbs discovered the fraud and gave notice to the customs in the North American ports. This report by Governor Thomas once again puts the lie to Oglethorp’s accusation. But, a small suspicion remains after reading the first customs declaration at table 1 of Chapter 18. There, we see deputy governor Benjamin Gumbs in 1765 declaring on oath that the two hogsheads of rum and eight barrels of muscovado sugar which he is shipping on the sloop Dispatch are from his plantation. And, who is the captain but one John Claxton?
The last famous pirate, all-be-it retired and reformed, whose name was linked to the Anguillians was Captain Woodes Rogers. Rogers enjoyed good connections close to the King. In 1718, he was appointed in his second term as Governor of the Bahamas. His mission was twofold. First, he was required to find sufficient settlers to make those islands productive. Second, he was charged to rid the area of his erstwhile piratical colleagues who infected those waters since the destruction of Port Royal. Port Royal at Palisados in Jamaica was a centre for English and Dutch privateers. They were encouraged by the English government to raid Spanish shipping in the Caribbean during the latter half of the seventeenth century. Port Royal was notorious for its gaudy display of wealth and loose living. It was destroyed by an earthquake which hit at 11:43 AM on the morning of 7 June 1692. Many of the survivors made their new pirate headquarters in the Bahamas.
Pursuing his first mission, Rogers tried for several months to remove the entire population from Anguilla to his colony. Some were perhaps enticed away, for Anguilla was going through one of her regular difficult phases. This was only one year after Abraham Howell made his last brave but unsuccessful attempt to settle Anguillians on Crab Island. The island continued to suffer throughout the second decade of the eighteenth century from the effects of a prolonged drought.
Some indication of how unbearable conditions in Anguilla were is provided by Governor Rogers' claim in a dispatch to the Committee that the entire population of Anguilla accepted his offer to transfer to the Bahamas. Anguilla was at that time, as he described it, a defenceless and barren island, with about 1,800 blacks and whites. The people were, he asserted in his dispatch, poor but industrious. He was anxious to have them relocate to the Bahamas as he observed that they lived in perfect friendliness with each other. They were of modest behaviour and their influence would help to reform the rough manners of the people then inhabiting the Bahamas. Governor Rogers was yet to learn that, though the Anguillians complain bitterly about their island, referring to it even today as ‘The Rock’, they were unwilling to give up one inch of it. It is unlikely that many of them removed to the Bahamas on the boat he sent to collect them.
The essentially hard-working and law-abiding nature of these early Anguillians is further emphasized by an incident recorded in the Colonial Office reports only two years later. In February 1720, deputy governor Walter Hamilton of Nevis reported to the Committee for Foreign Plantations on the fate of the crew of the pirate vessel the Royal Rover. Six of the pirates, five white and one black, landed on Anguilla pretending to be shipwrecked. They were, he wrote, either weary of that sort of life or they thought they had accumulated enough booty. However, they were detected by the Anguillians and captured and sent as prisoners to Nevis. There they were tried, found guilty and sentenced to death. It does not appear from this incident that the Anguillians were supportive of the pirates or their profession.
No other pirates from the Royal Rover were reported turned in, besides those that landed on Anguilla and were captured and delivered to the authorities by the Anguillians. Those that chose Tortola or Virgin Gorda to settle down got away scot-free. And, all of this while George Leonard, whom Christopher Codrington described as “an honest old sloop man . . . and having the best cotton plantation there,” was deputy governor of Anguilla. The favourable testimonies of Governors Rogers and Hamilton as to the character, not only of Leonard, but of the whole Anguillian community of that time, far outweigh the sly allusions and libellous remarks of the others (see illus 4 for Penny Slinger’s surrealistic depiction of both the Carib Raid and pirates at Sandy Ground).
4. Pirates and Caribs, by Penny Slinger,® depicting Road Bay in the background and the Road Salt Pond in the foreground.
As for the allegation of smuggling - that is something we may pass off with a knowing wink as a noble trade, until recently immensely important to the economy of the island. It was this profession that was responsible for giving valuable maritime training and employment for generations of Anguillian shipwrights and sailors. Of course, we have grown past that activity now.
 David A Mitchell, Pirates (1976).
 His source for this strange story may be Kemp and Lloyd, Bretheren of the Coast (1960), who wrote, “As for Sharp . . . in 1688 he is mentioned as commander, not quite governor, of the tiny island of Anguilla, otherwise known as Snake Island, the northernmost of the Leeward Islands.”
 Chapter 6: War and the Settlers.
 See for example, John Oldmixon, British Empire in America (1741), Vol 2, p.264-265.
 Instances have been mentioned earlier of Anguillians falling victims to pirates and privateers. See, for example, the 1686 deposition of Peter Battery at Chapter 6 and the report of the attacks on the island in and before 1688 by French pirates.
 CO.1/28, No 51, folio 121: John Knight’s 1672 petition.
 The 1670 Treaty of Madrid forbade the English from taking logwood from Spanish ships.
 CO.1/28, No 52, folio 121a: Privy Council to the King.
 CO.1/28: King Charles to Stapleton on 13 June 1672.
 CO.1/51, No 9: Stapleton to the Committee on 30 June 1683.
 CO.152/3, No 21, folio 90: Nevis Council to the Committee on 18 May 1699.
 CO.153/7, fol 379: Codrington to the Committee on 10 November 1701.
 CO.153/7, folio 387: William Popple to John Sampson on 22 January 1702.
 Acts of the Privy Council, Vol The Unbound Papers, para 621.
 CO.152/47, folio 98: Thomas to the Earl of Halifax on 26 March 1765.
 The Claxtons were a merchant family of St Kitts.
 CO.23/1: Rogers to the Committee.
 CO.152/13, folio 62: Hamilton to the Committee on 16 February 1720.