This work is a study of the first four generations of Anguillians. It deals mainly with the period 1650 to 1776. The period before the American Revolution is a special period for Anguillians. It marks the time when our ancestors claimed the land and worked it and held on to it despite all the conspiracies of Mother Nature and the colonial authorities to deprive us of the land. We got no consideration from either of them. What Anguillians learned from those early years was that there was no one looking out for Anguilla but ourselves. This work attempts to set out all that is known about these first Europeans and Africans, free and enslaved, who claimed this island. We shall search the archival records for documents that describe how they lived, what work they did, and the what tribulations they were put to. We shall try to explain how the tough times and disasters that Anguillians passed through in this early period contributed to build the characteristics of the proud and hardy Anguillians of today.
The earliest European recorded as landing on Anguilla was a Frenchman who made a brief call in 1564. Then, in March 1609, Captain Robert Harcourt out of Dartmouth was in the Rose on his way back to England from Guyana. This he took possession of "by turf and twig" in the name of King James I. He sailed through the cays on the north side of Anguilla. "There", he writes, "I think never Englishman sailed before us.” He did not stay on the island.
1. Sir Thomas Warner
It was only in 1623 that the first English settlement anywhere in the West Indies was made. That was the year that Thomas Warner, later Sir Thomas Warner (1580-1649), landed in St Christopher, more familiarly known as St Kitts, with a small band of settlers (see illus 1). He originally travelled to the Oyapoc Colony in 1620 in today’s Guyana as a captain under the command of Roger North. At the suggestion of Thomas Painton, another captain of the colony, he decided instead to try to colonise one of the islands of the Lesser Antilles because of their favourable conditions. In 1623 he abandoned his Guiana post and set sail north through the archipelago, deciding eventually to attempt a settlement on the island of St Kitts. That island is well named the ‘mother colony’ of the West Indies. It was from there that the English colonized Nevis, Antigua, Montserrat, St Croix, Tortola, Virgin Gorda and Anguilla.
The French joined the English in St Kitts in 1625. Pierre Belain d'Esnambuc (1585-1636), was a French trader. He settled at Dieppe Bay in St Kitts and was the first governor of the French part of the island.
2. Statue of Pierre Belain d’Esnambuc in Martinique
The English and the French were sharing the island of St Kitts when in 1629 Don Frederique de Toledo, Governor of Puerto Rico, descended on the two settlements with a strong fleet. Most of the French and English settlers in St Kitts escaped the Spanish attack by putting to sea. These refugees from St Kitts found hiding places among the lonely bays of the Virgins, Antigua and Anguilla. Some of them may have remained in Anguilla after the Spaniards abandoned St Kitts and Nevis, but there is no record that has survived from those days. D’Esnambuc later founded the French colony in St Pierre in Martinique in 1635 (see illus 2). The French from St Kitts subsequently settled not only Martinique, but also Guadeloupe, St Bartholomew, and St Martin.
The Dutch played a short but influential role in the settlement of Anguilla. They showed passing interest in the island in the 1620s as a source of salt. Johannes De Laet describes Anguilla in 1624 as having “no fresh water, but a salt pan with enough salt for two to three ships a year, and a beautiful bay”. But, he makes no suggestion that the Dutch settled the island. They did, however, have a short-lived presence. In about the year 1631, they built a fort at Sandy Hill on the south coast. It is likely that the purpose of the fort was to guard the sea approach to their settlement on nearby Sint Maarten. The site on top of the hill is still known as the ‘Old Fort’, though there is no trace left of any fortification or other Dutch occupation. In 1634, the Spanish destroyed the Dutch settlement at Phillipsburg in Sint Maarten. When the Dutch returned, they dismantled the fort on Anguilla. They used the materials to repair the battered defences of Philipsburg. That was the last time that the Dutch were to show any interest in Anguilla.
The official date of the English settlement of Anguilla is the year 1650. In that year, settlers from St Kitts and Nevis started a permanent, if unofficial, occupation of Anguilla. There is no reliable information on who these first settlers on Anguilla were. We do not have their names, or their country of origin. There are very few documents relating to Anguilla that survive from the seventeenth century.
We do not know the names of the first European and African settlers of Anguilla in 1650. As for the earlier indigenous Amerindian residents, they were long dead by that date. The Spaniards either removed them to slavery in Puerto Rico and Hispaniola, or, more likely, they died in their villages at Sandy Ground and Rendezvous Bay from diseases imported from Europe and Africa. The Amerindians had no natural immunities to the common infections of Europe and Africa. Influenza and measles were as deadly to them as smallpox and typhoid. This extinction occurred within a few decades of the discovery of the island in the 1490s. After that date, there is no mention in the surviving records of any Amerindians continuing to occupy it.
George Suckling claimed that Anguilla was possessed by the English, French and Dutch. But, he gives no authority for this assertion, which was made to him by residents of Tortola. All other seventeenth and eighteenth century references to the nationality of the first settlers are to the effect that they were English settlers from St Kitts. The possibility remains that Suckling’s account reflects early knowledge and is correct and that, prior to 1650, the island was informally occupied by unauthorised settlers of various nationalities. If so, they were unofficially occupying and working plots of land and held no title to them.
Dr Samuel B Jones was an Antiguan physician attached to the St Kitts colonial service (see illus 3). During the late 1920s, he held the post of Medical Officer, Magistrate and chief administrator of Anguilla. As he sat in the Magistrate's office awaiting the opening of court, he had access to the early deeds and records of Anguilla. After he read them, he wrote one of the earliest histories of the island based on the documents he read there. Dr Jones developed a special theory about the purpose of the 1650 settlement of the island. His theory was that the aims of the early English colonists who arrived in Anguilla in 1650 were both imperial and economic. He argued that the island was occupied by the English, not only to acquire more territory and to prevent other nationalities from seizing it, but also, from the planters’ point of view, because it provided additional land for cultivation.
3. Dr Samuel Benjamín Jones OBE
By the year 1648, both the Dutch and French established settlements on St Martin, which lay to the north and within sight of St Kitts. It seemed to the English, Dr Jones concluded, to be a good strategy to occupy Anguilla which lay eleven miles further to the north of St Martin. What few surviving written sources for that early period of Anguilla's history there are provide no evidence of any such imperial design in the colonization of Anguilla. Rather, the settlement of the island in 1650 is described by Charles de Rochefort as not having occurred “under any public encouragement”. De Rochefort was the pastor of the French protestant church at Rotterdam and resided several years in the West Indies. Du Tertre complained that his work was merely a revision of his work and that of Raymond Breton.
What is certain is that each early planter in Anguilla colonized for himself, and received no patent or title to his land. "Without any public encouragement" can only mean without commission from either Parliament or its Governor-in-Chief. Both Cromwell and the King gave official commissions to settle in other islands, in contrast with Anguilla. It would seem the better view that the island was first settled illegally and not as part of an imperialist strategy as suggested by Dr Jones.
The consequences of this lack of authority were to last for centuries. Anguilla would remain half-forgotten, lawless and desolate, until the demands for the abolition of slavery in England in 1825 were to force the Secretary of State to make provision for Anguilla to be included in the local legislation for abolition by bringing her under the authority of the St Kitts House of Assembly. One of the first St Kitts Acts passed specifically for Anguilla was the Slavery Abolition Act of 1825.
We can speculate that the first settlers from St Kitts were landless discontents who fled from St Kitts to take their chances on a lawless frontier. There was one other reason for leaving St Kitts, the taxes. By 1630, settlers paid yearly levies of 20 lbs of tobacco per head to the Proprietor, the Earl of Carlisle, 20 lbs to the Governor, 10 lbs to the church, and 40 lbs to maintain guards against the possibility of Carib attack for six years, even though such attacks temporarily ceased to be a problem. For the poorer homesteaders, moving to the lawless island of Anguilla was a major improvement in their condition.
Another argument against the imperial design theory is that throughout the remainder of the century, the Governors-in-Chief repeatedly express the view that the settlement in Anguilla is a nuisance. There is no suggestion in any of the early colonial dispatches that the settlement served any useful purpose, or that it was settled for strategic purposes. If this first settlement was unauthorized, the tradition recorded by Suckling that a mixture of English, French and Dutch possessed the island may well have some substance. Among the early illegal English settlers, most of them probably of the least reputable sort, some were fugitives of other nations. Some were debtors escaping from their creditors. But the English first accepted responsibility for the administration of the island, and after 1650 no other flag ever flew over it.
4. Distribution of the Lesser Antillean iguana
The 1666 John Davies of Kidwelly translation of de Rochefort was the earliest published description of Anguilla and of its first settlement. De Rochefort wrote that the island bore that name because of its shape, as it was very long and very narrow, lying like a snake or eel.
At a part where the island was widest, he claimed, there was a lake. He wrote that around this lake a few English families settled seven or eight years previously. When first settled, the island was “filled with alligators and other noxious animals”. The soil was good for raising tobacco and corn. The cattle imported multiplied very quickly.
The pond he refers to was probably Cauls Pond in the east of the island, or perhaps Road Pond in the west. We shall never know, as there are no land titles or correspondence from this early period that refer us to a particular pond. Some writers favour Road Pond. Cauls Pond is more likely since many of the deeds that survive from the seventeenth century relate to the Shoal Bay, Stoney Ground, and Cauls Pond areas. There are no early deeds that relate to Sandy Ground and Road Bay. That suggests that there was not much economic activity in Sandy Ground in the early period.
Despite what de Rochefort wrote, it is not likely that the first settlers found true alligators on the island. The lack of water, still one of Anguilla's most notable features, argues against it. The most probable explanation for the remark is that the slow-moving iguanas, which still exist in Anguilla, were mistakenly called alligators (see illus 4 and 5).
5. Iguana delicatissima
The ground lizard is another candidate. They can both grow to nearly three feet in length. If there were ever alligators on Anguilla, their remains would turn up in the various archaeological excavations that took place over the past decades. No trace of any alligator remains are reported from any part of Anguilla.
As for the reference to noxious animals, the harmless racer snake, which is still commonly seen throughout the island and which to its own disadvantage still inspires an instinctive dread, may be the source of this statement.
6. The common ground lizard
Scorpions, centipedes, and other insects such as mosquitoes and sand flies, could also have accounted for the words ‘noxious animals’, but their stings are not fatal. The name Merrywing Pond at Cove Bay memorialises the seventeenth century name of the mosquitoes and sand flies that still infest the island during and after periods of rain.
We must also take issue with De Rochefort’s suggestion that the name of the island derives from its eel-like shape. It is more likely that the name derives from the many harmless racer snakes that live on the island.
The word ‘Anguilla’ is the Latin for eel. The scientific name for the common eel is ‘Anguilla anguilla’. An eel may be described as a form of sea snake. Bolstering this theory that the island is named for its snakes is the suggestion that the early English had, as an alternative name for Anguilla, the name ‘Snake Island’. We shall look at this aspect of the name of the island when we come to deal with the subject of the connection of the buccaneers to the history of Anguilla.
De Rochefort tells us that the first cash crop of these early settlers was tobacco. This was a native Amerindian crop found growing also in St Kitts, Nevis, and Antigua when the settlers arrived in those islands. It was the first cash crop of choice of the earliest settlers in St Kitts and Anguilla. It did not last long. Once Virginia's tobacco fields began to flood England with vast supplies of this produce the islands could not compete. In all the islands, the crop ceased to be significant by the 1640s and alternatives were found.
Cotton grew on the island, as in the other Leewards, where the Indians cultivated it before the arrival of the Europeans. Taken up by the early settlers, it found a ready market in Europe. Within a short time cotton replaced tobacco as the cash crop of the early settlers. Portuguese Jews fleeing prosecution in Brazil brought sugar technology to Barbados in about 1640. But, sugar cane cultivation was not attempted in the Leeward Islands for several more decades. No serious attempt at growing sugar cane was made in Anguilla for a century after it was established in Barbados. The sugar period for Anguilla was roughly 1730-1776.
De Rochefort confirms that the earliest settlers on Anguilla grew corn for food. It remained a popular cash crop and source of food widely grown throughout the island until recent years when tourism became the modern crop of choice. Corn, or, more properly, maize, was an Amerindian food crop widespread throughout the West Indies. There was no need to import it into Anguilla, as it was found on the island when the settlers arrived. Cassava, or manioc, was the principal root crop of the natives, and it has continued to be a popular starch among the islanders. Cattle, sheep, goats and pigs imported from Europe were also kept for food.
No sooner did this first settlement of 1650 establish itself, than six years later it was almost wiped out by an Amerindian attack. Pere Jean-Baptiste du Tertre recorded that the Caribs attacked the inhabitants of St Barts, where they killed sixteen and wounded several others. From there, they went on to Anguilla where they killed almost all the men. They plundered and burned the houses, and kept the women and children as slaves. The indefatigable du Tertre witnessed the aftermath of this Indian raid. His account is the only contemporary description we have of the event. The boat that he was sailing in was on its way from Guadeloupe to St Kitts on the morning of 18 November 1656. Near the island of Redonda it came upon the Amerindians as they paddled away from Anguilla. There were in all nine large pirogues, or canoes, filled with men. Fortunately for the French, all nine pirogues did not attack the French vessel. This is what du Tertre wrote about the encounter:
I saw them first, to the number of nine pirogues, which looked at a distance only like pieces of timber floating on the water, and showed them to Captain la Bourlette, who said after he had looked at them, "Father, if we were in any other place, I would think that it was an army of savages going upon some expedition."
But a moment afterwards, seeing them tack, he cried out, "Get ready! Get ready! They are the savages!" As they were still a full league from us, we had time to prepare for action, and to say some short and fervent prayers.
The largest pirogue, leaving the eight others, came boldly to reconnoitre us. Our Captain did what he could to run her on board athwart ships, and sail over her; but the Caribs adroitly avoided the shock and always kept her head towards us.
We had pointed the gun to rake the pirogue from one end to the other, and it was loaded with a large ball, an iron chain, and two bags of old nails and musket balls. Half the savages on board the pirogue rowed; all the others held each of them two arrows on their bow-string ready to let fly.
When they were about twenty paces from us they made great cries and hootings on coming to attack us; but as we went to them before the wind, the foresail covered us and they could not see to fire at us.
Our gunner seeing them close chose his time so well, and let off his gun so a propos that the discharge knocked down more than half the savages, and if the stern of the pirogue had not pitched, not one of them would have escaped. There were more than twenty killed by this discharge so that the sea all around our bark became bloody and the pirogue was stove and full of water.
They did not for that cease to close to us, and those that had escaped seeing us clear of the sail shot a number of arrows and wounded two of our soldiers, one in the finger, which was cut off the next day, and the other in the thigh, who died a few days afterwards at Martinique.
Our two Captains and our soldiers fired their pieces, and because they were so close there was scarcely one that did not kill a savage. While both sides were fighting valiantly an old captain of the savages, seeing M. de Maubray upon the poop shot an arrow at him with such violence that it broke the vessel's bell without which he would have been killed. But he did not endure that long: M. de Maubray immediately shot him in the side. The ball passed through him, and M. de Maubray would have finished him with his pistol, but the savage avoided him and threw himself into the sea, with his bow and arrow, where all the others, even the wounded, followed him!
As soon as they were all in the water we tried to save some prisoners that were in the pirogue, and easily got out two young Frenchmen. But as we were trying to get an English girl out, an old female savage bit her on the shoulder, and tore out as much flesh as her mouth could hold! But at the same time a Christian Carib that we had on board, and a sworn enemy to others of his nation, struck her a blow with a half pike in the neck, which made her drop her prize. This wound, nevertheless, did not prevent her from throwing herself upon the girl and biting her a second time, before we could get her out of the pirogue. A Negro who had lost both his legs by our shot refused the hand which was held out to save him, he threw himself head foremost into the sea. But his feet not being quite separated from his legs, he hung by the bones and drowned himself. We also tried to save a young English lady, the mistress of the girl we had taken on board. The pirogue being separated from the bark, we saw her for some time upon a chest, holding out her hands to us; but as we went to her the chest upset and we never saw her again!
While we were occupied in saving these poor miserable creatures, our old savage captain all wounded as he was came towards us, and raising his body half out the water, like a Triton, holding two arrows on the string of his bow, fired them into the bark and dived immediately under the water. He returned thus bravely to the charge five times; and his strength failing him before his courage, we saw him fall backwards and sink to the bottom!
Another old man who had remained on the bark's rudder having lost his hold, began to cry out, and implore us not to kill him. I instantly begged Captain Bourlotte who to satisfy me threw a rope's end to him, but he could not catch it, and seeing that he used all his efforts to regain the bark, Bourlotte shot him in the face, and he sank to the bottom.
In the beginning of the action I had seen a young savage in the water that could not be more than two years old, moving his little hands, but it was impossible to save him.
If the eight pirogues had come to us with the same courage we would certainly have been taken; but having seen the fire that we kept upon the first and perceiving that we stood towards them with all sail set, they took flight, and having gained the weather gage by rowing they saved themselves on a small island called Redonda.
We have little information on how many of the Anguillian settlers survived this attack, or their names. Around this time the Anguillians elected Abraham Howell to be their governor. Abraham Howell, whose courage and character were frequently tested during his long life, survived to restore the fledgling colony. Contrary to du Tertre's report of total destruction, it is more probable that the raid was the typical hit and run affair favoured by the less well armed Indians. It is likely that only stragglers and isolated settlers were killed or taken prisoner. The bulk of the men and their families survived. The settlement was revived and continued to grow.
Although there is no record of the names of the first settlers on Anguilla at this time, it is possible to reconstruct a partial list from the surviving documents. The records all refer to ‘a few English’ being responsible for the first settlement. A good guess would be that the island sloop that brought them, their families and their possessions, would not have held more than twenty-five men. A few of them would survive, we cannot say prosper, until the end of the century. The majority of them appear to die in the many violent conflicts to which the island was subject and from disease and accident. Those we can be relatively sure of include:
Abraham Howell [elected deputy governor in 1666, which suggests that he was at least 25 years old when elected]
George Leonard [over 80 years of age when he died in 1735]
John Mereweather [member of Council in 1672].
Richard Richardson [member of Council in 1672].
Humphrie Seward [member of Council in 1672].
The marvel is that, in those early days of the first generation of Anguillians, the struggling settlement was never abandoned in spite of the hardships involved. For every settler killed by marauders or lured away to greener islands, two arrived in Anguilla to take his place. The evidence, skimpy though it is, of continuous occupation throughout the remaining years of the seventeenth century can be sifted from the Governor-in-Chiefs' dispatches back to London, and a few surviving Anguillian title deeds and conveyances of this period. We shall look at some of them next.
 Thomas Southey, Chronological History of the West Indies (3 vols, 1827) Vol 1, p.189.
 Robert Harcourt, A Relation of a Voyage to Guiana (1616), cited by Southey, op cit, p.243
 Southey, op cit, Vol 1, p.265.
 Johannes De Laet, History of the New World (1625). De Laet (1581-1649) was a Dutch geographer and director of the Dutch West India Company.
 Cornelis Goslinga, The Dutch in the Caribbean (1971) p.129.
 George Suckling, An Historical Account of the Virgin Islands in the West Indies (1780).
 Just as I did fifty years later while I served as Magistrate of Anguilla from 1976 to 1980.
 John Davies, History of the Caribby Islands (1666). A translation of Charles de Rochefort, Histoire Naturelle et Morale des Isles Antilles de L'Amerique (1658). The comparative scarcity of the Davies’ translation is claimed to be due to the burning of the majority of copies in the Great Fire of London in September 1666.
 James A Williamson, The Caribbee Islands under the Proprietary Patents (1925), cited in David Watts, The West Indies: Patterns of Development, Culture and Environmental Change since 1492, p.148.
 Cited also by Thomas Southey, op cit, p.328.
 The Encyclopaedia Britannica entry for Anguilla preserves this alternative name. See also Chapter 8: The Buccaneers and Anguilla.
 Chapter 18: Sugar Arrives.
 Columbus himself preserved the Amerindian name for this grain when he described it growing in the Bahamas on his first voyage in 1492.
 According to a story told me by an elderly resident of Long Bay Village, local legend has it that Maids Bay is so-called from the translation of the original name of the place, La Baia de Maiz, or Maize Bay. On the map it is now incorrectly spelled "Meads" Bay. No person named ‘Mead' is ever recorded as living in Anguilla, far less in the Maids Bay area. ‘Mead’s Bay’ is still pronounced by locals as ‘Maids Bay’, or, more correctly, ‘Maize Bay’.
 Jean-Baptiste du Tertre, Histoire General des Isles de St Christophe, de la Guadeloupe, de la Martinique, et autres dans L’Amerique, Tome 1, p.508. [Translated by Capt Thomas Southey, A Chronological History of the West Indies (1827), Vol 2, p.15-18]