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  In 1644 the Netherlands and England considered each other firm Protestant allies, linked by memories of decades-long combat against Papist Spain. Relations between their New World colonies were sometimes strained by territorial disputes, but they steered clear of outright war. When, for example, the Dutch explorer David Pieterzen de Vries ventured south from New Amsterdam to Virginia in 1633, he enjoyed “a Venice glass of sack” with the English governor, Sir John Harvey. The two politely sparred over boundaries, with Harvey allowing that there was land enough for both. If the Dutch “did not come too near us,” he said, then the two nations should “be good neighbors with each other.”

  During the month of February 1644 the Seerobbe’s Dutch captain, Sijmon Dircxsz, steered up and down the Chesapeake’s treacherous tidal rivers, stopping at plantation wharves to load heavy hogsheads of cured leaf. Nathaniel would have seen a few black faces at wealthier plantations, but the Virginia that he viewed from the James was still largely a place where a freed servant could farm a small tract with a few white bondsmen. (Slaves were in short supply, as slave traders were more interested in supplying South America and the Caribbean.) Those small operations would largely vanish in the following two decades, to be replaced by large plantations worked by Africans as England entered the transatlantic slave trade with enthusiasm.

  Although miles of “sweet-scented tobacco” lined the riverbanks, the tobacco market fluctuated violently in the early seventeenth century. De Vries noted, “He who wishes to trade here must keep a house here and continue all the year, that he may be prepared when the tobacco comes from the field to seize it,” but at other times an oversupply caused a depression. Nathaniel and a consortium of other buyers got shorted on this trip: they had contracted to take on a hundred and fifty barrels, but were able to load only forty-three.

  As required by law, Nathaniel had stopped first at the colony’s capital, “Jemston,” as the Dutch record spells it. There he had offloaded “Commodytyes” so desired by planters, such as hats, both “Browd & brimd,” and “thred stockens … new fashioned shoes … pinnes … tuffted Holland” (a fine Dutch linen), and “wines and spirits.” Prosperous “James Cittie,” then in its fourth decade, had survived starvation, drought, epidemics, bankruptcy, hostile government takeovers, and Indian attacks. After this halting start, Jamestown was on its way as the urban center of the Tidewater region. Long before 1644, the first miserable Virginia Company settlement of 1607 had burst out of the original palisaded fort and spread into a “New Towne” with a church, warehouses, shops, taverns, stocks, gallows, and a single brick house considered “the fairest that eer was knowen in this countrye,” which would surely not have impressed Amsterdam-bred Nathaniel. As of 1643, it also boasted the first bicameral representative government in the colonies.

  Nathaniel probably kept his mouth shut on his religious and political views in Virginia, an Anglican colony loyal to the crown. In April, two weeks before the Seerobbe sailed for home, David de Vries witnessed two London ships manned by Parliamentarians engage a fly-boat (a fast frigate) from Bristol filled with royalist sympathizers in a sharp firefight. The short battle ended in a draw, but afterward the Londoners feared to land “because all the people of the country were in favour of the king” and left Virginia without a shred of tobacco. Given Nathaniel’s Separatist upbringing, what wonder is it that in 1651 he and his partners, all Parliamentary sympathizers, set up their plantation in the Puritan homeground of New England (of which Long Island was then considered a part)?

  His Virginian stay lasted some months, perhaps even as long as a year—certainly long enough to get a taste of the climate. Much later, writing to John Winthrop Jr., the governor of Connecticut, from Shelter Island, he remarked that Tidewater winters were more moderate than those up north, but that Virginia “is more Unhelthie than N. England.” Nathaniel may have contracted what we now know is mosquito-borne malaria, then thought to be caused by noxious swamp vapors. In a much later letter to Governor Winthrop, a noted apothecary and healer, Nathaniel complained of chronic bouts of ague, nausea, and stomach pain—all symptoms of malaria. Winthrop carefully labeled this missive as “Capt Sylvestters note about his Sicknesse.”

  Two weeks before the Seerobbe sailed from Kecoughtan, leaving Nathaniel to face the “Unhelthie” summer, coastal Virginia had exploded in war, the third attempt by the region’s united Indians to push the English out. Some of the major attacks occurred on the lower side of the James River, where Nathaniel was trading at Blunt Point, some thirty-five miles downstream from Jamestown. Four to five hundred colonists were killed. The English retaliated with a summer campaign, destroying villages and burning fields. The Indian leader Opechancanough, Powhatan’s brother or cousin, was captured, imprisoned, and shot in the back by a soldier.

  “He Would Rather Lose His Right Hand”

  Nathaniel made his way from Virginia to the West Indies by the spring of 1645, where the Seerobbe picked him up on another transatlantic round, either on Barbados or St. Kitts, the last port on a typical Caribbean trading circuit. Trading partnerships like the Sylvesters’ kinship network made for voyages that stopped in many ports as they carried shorthaul freight from island to island as well as long Atlantic trips. It was in St. Kitts that Arent Gerritss, a longtime West Indies Company employee, hopped aboard for the fifteen-week trip home to Holland. The company designated him as its supercargo, or official representative, on this trip, meaning that the Seerobbe sailed under WIC orders.

  Two years later, Gerritss and Reijer Evertsen, the steersman of the Seerobbe, testified to the company’s board of directors that there were 2,911 rolls of tobacco in the ship’s hold. Each roll bore a merchant’s mark or initials or had been set aside as a crewman’s share. (One hundred rolls were marked NS, for Nathaniel Sylvester.) There were also forty-five prime beaver pelts, twenty-four bales of cotton, thirty-four casks of candied fruit (Evertsen ate some, he confessed), eight and a half hogsheads of sugar, a hundred and forty pounds of indigo (property of the captain), and half a hogshead of cochineal, an expensive crimson dye. Everything listed could have been produced or grown in the Caribbean or South America except the beaver skins, which had to have been taken in North America. My bet is they came aboard in Virginia, thanks to Nathaniel. Evertsen watched as Captain Dircxsz signed the bills of lading to deliver the goods from St. Kitts to Amsterdam, “which would be the right place to unload.” Similar documents were diligently signed at every port and duly noted by Evertson or Gerritss.

  The Sylvester documents in the Amsterdam notarial archives record contracts, executed or broken, as well as infringements of the law, disputes (Giles and his barrels), and complaints. It’s rare that the accused looks good in them. Their abundant detail often makes them seem tantalizingly clear, but I have to remember they have been wrenched from their seventeenth-century context and were written for purposes that often don’t exist on the page. Gerrittss’s and Evertsen’s testimony, which stretches over two long documents and a period of years, is a good example. It’s pretty clear that the company was “shadowing” the Sylvesters. Indeed, the family already had a record for illegally evading payment of WIC duties in 1646, when Gerritss first alerted his superiors. Curiously, there is no record of any punishment or fine levied against the Sylvesters, even though the file remained open: in 1649, a duplicate report was sent to the WIC director, who had heard Evertsen’s testimony. Beyond that, nothing.

  Dutch maritime regulations stipulated that the merchant who owned a ship had the right to set its course. (If the merchant wasn’t aboard, the captain had to follow a plan laid out in the original contract.) In November, when the Seerobbe neared the European coast, Nathaniel took charge.

  “On the way back here,” Gerritss testified, “having arrived at the Channel of England, at forty-nine degrees and some minutes North altitude, the said captain and merchant changed course to La Rochelle in France or the island of St. Martin opposite to it, even though the wind was more expedient for sailing into t
he Channel than for sailing to France, and they would have arrived soon[er] than at St. Martin.” Nathaniel and his ship were just south of Land’s End, approaching the mouth of the English Channel, closer, given the wind conditions, to Texel than to France. “Also they did not need light, sails, ropes, water, food or anything else,” Gerritss added, “[They went] of their own will alone, under pretext of looking for a convoy [for protection against privateers].” The French port of La Rochelle and the smaller harbor of St. Martin on the Île de Ré, less than half a mile off the coast at La Rochelle, lay outside WIC jurisdiction. Nathaniel could escape WIC taxes on any goods he unloaded.

  Then the clincher: “the merchant having said before that he would rather lose his right hand than not come to France on that trip.” Here is the unmistakable voice of Nathaniel, whom I will hear again throughout his life. Even with Gerritss aboard, Nathaniel apparently was willing to gamble on the chance that the WIC authorities in the Netherlands would not catch up with him—or he didn’t care if they did. At twenty-six or so, this Calvinist merchant had the stuff of a stubborn renegade.

  4

  THE OTHER ISLAND: BARBADOS

  Merchant’s Mark

  Two field school students stand over a wheelbarrow at the manor, shaking a wood-framed screen that sieves soil particles into a wheelbarrow below, leaving on the mesh whatever is too big to pass through. A small, dark blob glows among the pebbles. Vaguely oval, it’s about three-eighths of an inch long. Steve Mrozowski picks it up and pronounces it a bale seal, made of lead. Soft lead folds easily: what was cast as a rough blank about the size of a nickel was then stamped and crimped securely over baling string. The markings on this one are illegible. The trail of such ID tags runs from Russia to South America, from the thirteenth century to the nineteenth. They marked commercial goods in transit and kept track of mixed shipments such as those the Seerobbe carried. Combinations of initials, numbers, and armorials, as well as symbols like a fleur-de-lys or cross, distinguished each “merchant’s mark.”

  No recognizable Sylvester insignia are stamped on the bale seals found at the manor, but Nathaniel’s elder brother, Constant, drew his mark in the margin of a 1659 letter from Barbados to John Winthrop Jr., whom he had just visited in Connecticut, thanking Winthrop for “ye many civilities.” Constant sent him a “Case of Such Sugars as my plantation doth yeeld.” Constant used the device as a personal emblem, almost a coat of arms, just as the Sylvesters of Burford, the center of England’s wool trade, used similar marks as heraldic devices on their tombs in the sixteenth century.

  So far, no connection has emerged between the branches of the family, but the marks and the name clearly link them. These kinfolk also knew about the New World. In 1569 the husband of Agnes Sylvester, Edmund Harman, had a startling family memorial carved in the Burford church. Around the central cartouche, four sexy naked men and women in feather crowns, perhaps representing Tupinambas from coastal Brazil, dangle bunches of what look like gourds and bananas. Lithe and ferocious, these figures once exhaled the exotic fragrance of “the Indies,” an alluring mix of riches, wonders, danger, and the barbarous, beauteous “Other” that had penetrated deep into European consciousness a century before the Sylvesters sailed into Bridgetown, Barbados.

  On the Island of Barbados

  By July 1646, when Nathaniel and the Seerobbe returned from La Rochelle to Barbados, his family had been doing business there for seven years. His father, Giles, was directly involved in Barbadian trade as a purchaser on his own account and as a broker as early as 1639. By 1646, the island had seen the beginnings of the changeover from cotton, indigo, and tobacco as staple crops, grown and harvested mostly by white indentured servants or small farmers, to sugar, produced by a labor force of enslaved Africans. By 1646, Nathaniel’s elder brother, Constant, had already purchased plantations and a plot for a warehouse on the Bridgetown harbor waterfront. The family network was smoothly transitioning to sugar.

  As Nathaniel sailed back across the Caribbean, the island, a soft mound of dense tropical green only 166 square miles in extent, would have appeared before him, floating on the sea. I followed him there. The island was green—uniform cane fields surrounding a ragged mountainous spine—not the patchwork of remaining forest and fields of cotton, tobacco, indigo, and cane that Nathaniel first knew in the 1640s. Constant Plantation, one of the three that belonged to Constant Sylvester, still produces sugar today, and just as at Sylvester Manor, an eighteenth-century house still stands.

  To the left of Constant Sylvester’s merchant’s mark, “C.S.,” are the much smaller initals “N.S.,” which probably stand for “Nathaniel Sylvester.”

  I hunted through the Barbadian archives to track down the growth of the Sylvesters’ wealth and to research the politics that catapulted the four partners into purchasing Shelter Island in 1651, a purchase made possible by sugar and paid for in sugar. In 1651, as Barbados became embroiled in the English Civil War, Parliamentarians such as Constant Sylvester and Thomas Middleton were exiled. They bought Shelter Island as a bolt-hole in case the monarchy won and they lost their plantations. But only months later, in January 1652, Oliver Cromwell’s fleet conquered Barbados in a nearly bloodless siege. Constant and Middleton rushed back to Barbados, became members of the Barbados Council and Assembly, and positioned Nathaniel on Shelter Island to develop it. The Barbadian plantations provided start-up capital for Shelter Island and the primary market for what Nathaniel produced. Just as he was the junior partner, so his island (as he came to think of it) was of secondary importance.

  In the Barbadian National Archive, in the hot, high-ceilinged, white-painted main room where scores of people quietly turned pages of the ancient deeds registers, I learned that it was from Constant and other planters that Nathaniel came face-to-face with the practice of slavery. From the first he was apparently prepared to stock the Northern plantation with Africans. West Indian planters’ profit-driven brutality and savage disregard for human life are not news; an immense literature exists on the subject. But what I found out about slavery at seventeenth-century West Indian plantations became the information that must stand in for all I don’t know about the control—through coercion, cruelty, and fear—of enslaved labor on Shelter Island during the first thirty years of European settlement. Without comprehending the conditions that Nathaniel must have seen and grasped on Barbados, my speculations about the Sylvesters’ early Shelter Island life are worth little. Long Island’s different imperatives included controlling a volatile mixed workforce of enslaved Africans and Indians, and a few indentured white servants, living together under crowded conditions in a cold climate—and growing crops less valuable than the sugar that made Barbadian slaves expendable and easily replaced. The concept of human chattel as the predominant source of labor was the same on both islands. Edgar McManus, author of Black Bondage in the North, notes that “the principal formative influence on slavery came from the West Indies,” although, he continues, “the North did not adopt the harsh codes of the islands completely, for some changes had to be made for local needs and conditions.”

  Richard Ligon’s A True and Exact History of the Island of Barbados provides the most comprehensive record of the island as it became a sugar colony between 1647 and 1650. About his arrival from England, as his ship “past along the shoar” toward the island capital of Bridgetown in 1647, Ligon wrote, “The nearer we came, the more beautiful it appeared … There we saw the high large and lofty trees, with their spreading branches and flourishing tops … return their cool shade to secure and shelter them from the Suns heat, which without it would scorch and dry away.” Mangroves flourished in coastal wetlands. Beaches were fringed with sea grapes dangling their long bunches of fruit, and by salt-tolerant trees such as whitewood, flushed with pale pink trumpet flowers, and manchineel, whose sap was used to make poison for Carib and Arawak arrows. Smooth-skinned manatees, the Rubenesque mermaids of seafarers’ sex-deprived imaginations, grazed placidly on seaweed. Hummingbirds “not much big
ger than an humble Bee” hovered at the flowers, “never sitting, but purring” with their wings. Poisonous scorpions, their jointed limbs as translucent as moonstones, dreamed under the bark of trees, or scuttled, barbed tails raised like banners, from beneath the leaf litter of the forest floor. For white colonists like the Sylvesters or Richard Ligon (who became a plantation manager), the immense, florid wilderness contained as much danger as beauty and promise.

  The several hundred plantations whose sugar mills are shown on Richard Ford’s 1674 A New Map of the Island of Barbadoes had made the island the most successful of all British colonies by that date. Bridgetown, the principal port where Constant Sylvester’s shipping warehouse stood, is at left, above Needham’s Point. (Map courtesy of the John Carter Brown Library at Brown University)

  The appearance of tropical abundance was deceptive: the ecology of a seasonal rain forest is fragile and its soils are easily depleted once tree cover disappears. By 1646, deforestation was well under way. In the decades following their initial settlement in 1627, colonists planted market crops for export—tobacco, cotton, ginger, indigo—as well as food for themselves and their white indentured servants, and African slaves. Disease and Spanish slavers had eradicated the Amerindian population by 1536, so the settlers had no natives to contend with. Commercial sugar production was still a trial-and-error affair in the late 1640s, although by 1644 James Drax, Barbados’s richest planter, had grown, processed, and sold enough sugar to pay for thirty-four Africans. By 1654, not long after Nathaniel had made another trip to Barbados from New England, Drax would have two hundred Africans slaving on his lands. Ligon singles out Drax and another major planter, Humphrey Walrond (whose daughter Grace would marry Constant in 1660 or 1661), as models of prosperity and success.