Piracy is as old as the art of transportation by water. The first Phoenician boatmen feared pirates even more than they did
resentful sea gods, vicious sea monsters, and spiteful giant sea rocks who ganged up to crush ships—a common nemesis,
if Phoenician maritime annals are to be believed.
But it was not until the Sixteenth Century, and the onset of transatlantic imperialism, that piracy entered the realm
of common dinnertime topic. “Imperialism,” in that day, meant countless Spanish galleons returning home along
the “Spanish Main” listing from tons of gold stolen (or, according to some Spanish sources, received as part of
fair business transactions) from the Aztecs and Incas.
The growing number of sailors in turn stealing the stolen gold problem became for all of the Colonial Empires. According
to British Royal Navy, in 1563, there were four hundred such pirates known to be sailing the Four Seas, and the number was
increasing daily. In naval service, as well as on merchant ships, pay was poor and rations worse. The menu consisted solely
of cold hardtack biscuits accompanied by salt beef, salt pork or salt fish—called “Hairy Willy.” But it
was the puny ration of grog (rum diluted with water to stretch supplies) that irked the men most of all, and ranked among
their chief motivations for going “on the account” (pirate for “pirating”). Ironically, many of these
men had enlisted in the Navy in hope that the very same grog limit, as well as the job’s regular hours and strenuous
exercise, might provide an asylum for their alcoholism.
Then there were the conditions. Hard work was the least of it. On overcrowded man o’ wars—frequently crewed
by five hundred—space was so limited that a man could scarcely move without brushing against another. Something as
simple as how a man gargled could, over time, so grate on a shipmate’s nerves that no one would be shocked if the gargler
“fell overboard” on a dark night, never to be found. On the infrequent occasions the men were given the respite
of sleep, they had to do so in hammocks eighteen inches wide, to a lullaby of the snoring of dozens of others who hadn’t
bathed in months and were crammed side to side and above and below one another. On hot nights, the hammocks proved veritable
frying pans. On cold, the men longed for the hot.
Many more sailors suffered—though they likely wouldn’t have put is as such—psychologically. The frequent
summons of “All hands witness punishment ahoy!” sent a shudder through all but the stoutest of hearts. Incessant
floggings made many sailors feel like beasts, rather than men. And the long lists of rules made the sailors who still felt
like men feel like children. Most man o’ war captains forbade the sordid game of draughts (checkers).
As consequence of all this, many a cold nasty night was warmed by tales of pirate voyages to places where the weather
was fair, the water easy and the lasses both fair and easy. Furthermore, there was tobacco, grub aplenty, and rivers of grog,
and the only time quarters were cramped was because they were stacked starboard to larboard with gold doubloons.
Others, for whom grub and lasses held less appeal, found themselves persuaded to go on the account simply by the increasing
occupational hazard of being an honest sailorman. For instance, between 1569 and 1616, nearly five hundred British ships
were captured by the Barbary pirates, who cut the throats of those captives deemed not worth the trouble of feeding and transporting
to the slave market. It is due to such practices, some historians theorize, that the term “barbarian” came to
mean more than simply a native of Barbary.
By 1618, the number of pirates had leapt to nearly five thousand. Much of the action was in the Caribbean. This was
due as much to its placement smack on European merchant ship routes, as to its islands’ aesthetic appeal. As French
missionary-turned-lawman Captain François Malebarre observed in his 1621 book Catching Pyrats, “A cheap and
abundant supply of strong beverage and a cheap and abundant supply of nubile woman tragically uneducated in virtue has turned
the Caribbean into the Sea Devil’s Playground.”
Among the principal players was Abraham Cooke. In 1628, at the age of seventeen, Abraham had emigrated from Wales to
the Caribbean as part of a rush of adventurers like that of the ’Forty-Niners two centuries later, except the objective,
at first, was not gold, but cows. The Spanish had virtually exterminated the Indians who’d inhabited St. Kitts and
the nearby islands of Tortugas and Hispaniola, leaving herds of wild cattle almost as great as the European demand for beef
and hides. Abraham joined the growing ranks of the “buccaneers,” as they became known because of the “boucane”
in which they smoked the meat. “Buccaneer” took on its current meaning when men like Abraham Cooke realized that,
while selling meat to a passing Spanish ship was lucrative, seizing the ship and taking its entire store of gold was much
A key to the buccaneers’ success was the cutlass. The short-bladed butchering knife was easier to wield on a crowded
deck than traditional swords. As time passed, and cutlasses became the weapon in everybody’s baldric, the lone—and
seldom-used—distinction between “pirate” and “buccaneer” became that the former considered any
ship fair game while the latter sailed clear of those flying the flag of his own nation.
Abraham Cooke and his band of onetime herders captured eleven Spanish merchant ships. With the proceeds, they built
mansions in Port Royal of which, it’s said, the doors were made of gold.
Their first—and last—misstep was engaging a small Spanish merchant ship on a cool November evening in 1648.
Unbeknownst to them, the merchant ship was transporting a Spanish Naval contingent.
The merchantman’s captain had been approached a few days earlier by a failed buccaneer named Cyril Hood. Hood
promised, if given 100 philips, to provide information on a forthcoming buccaneer raid. The captain dismissed Hood as a swindler—the
buccaneers never sold one another out. But when the financially and otherwise hard-up Hood lowered his request to only the
price of a bottle of rum and a roll in a hammock with a doxy, the captain thought, “Why not?”
Abraham Cooke and his fellow bucs died in the subsequent fighting. The good news was they did so quickly, and they were
avenged. A drunken Cyril Hood spent the following day—his last—as a jib sail, on a barque belonging to Abraham’s
cousin Abel Cooke.
Hood’s kin in turn sought vengeance. Their man, they claimed, had simply accepted a gratuity from the merchantman
for navigational aid. As for the doxy, they maintained she’d been his girlfriend. The fact that she had had twenty-three
other boyfriends, that week alone, did not mitigate Cyril’s martyrdom in their eyes, which, it should be noted, were
usually bloodshot. Thus commenced several generations worth of enmity between the Cookes and Hoods, which has continued into
the Twenty-first Century.
Infighting aside, the pirate business was thriving. Abraham Cooke’s fate was an exception. In general, the authorities
were proving toothless. The European governments lacked both the unity and the funds necessary to create an adequate patrol
The harshest action against pirates was taken not by any military force but, rather, by local missionaries. No sooner
was the existence of a place known, it seemed, than missionaries obtained leave to establish themselves in it to Christianize
and otherwise enlighten the natives. The missionaries sought to “reform the pyrats of their foul practice of cursing.”
That the pyrats hacked good Christians heads off during robberies was evidently lower on the missionaries’ list of objections.
Piracy in the Caribbean swelled to the point that, by the latter half of the Seventeenth century, the European governments
effectively threw up their hands and adopted a policy of “if-you-can’t-beat-’em-join-’em.”
Pirates were designated “privateers” when they bought or were otherwise granted a “letter of marque and
reprisal” by their own governments. These were essentially licenses to prey upon the ships of nations with whom the
issuing nation was at war, which, often as not in those days, was just about everybody.
Pirates become de facto government employees—the more successful receiving colonial political appointments. Henry
Morgan, the greatest of all buccaneers, was awarded the governorship of Jamaica, as well as a Knighthood. Another pirate,
Lancelot Blackburne, ascended as far as Archbishop of York. Ironically, both of these pirates, prior to receiving their commissions
as “privateers,” had been referred to as “homicidal maniacs”—and worse—by the very men
who commissioned them. It will come as a shock to no one that those men were politicians.
One of the great privateers of the day was Ezekiel Cooke. As a young man on St. Kitts, the lust for adventure in Ezekiel’s
blood was not at all diminished by the fate of his father, Abraham. In 1669, Ezekiel apprenticed with Henry Morgan (of note,
he married Morgan’s daughter, Rebecca, in 1677). In 1673, he undertook heavy debt to buy his own vessel, a swift, ninety-four-foot
brigantine, the Quedah. To his creditors’ delight, Ezekiel proved masterful. He created a barroom intelligence
network to ascertain Spanish navigational plans, he conceived militarily brilliant raids and, perhaps most impressive of all,
he kept his men clear-headed and motivated—pirates were always drunk—by telling them that their grog had been
poisoned by the Spaniards.
Over the years, Ezekiel Cooke and his crew plundered more than fifty Spanish craft, and, on one occasion, an entire Spanish
settlement. A good privateer never lacked in courage. A great one tempered it with discretion. Ezekiel’s unique record
was a function of knowing when to avoid a fight. Like many of the Cookes, he also knew how to sail, possessing an instinctive
ability to push a vessel beyond the limits others thought possible. And like a chess master, he maneuvered in such fashion
that he could take a prize, get away while sustaining minimal damage, and avoid the risk of being overtaken by a superior
ship. Toward those ends, he liked to travel with a fast companion ship. Once he sighted a convoy of merchantmen, the companion
approached them, feigning attack, but really intending nothing more than to expose herself to the merchantmen’s armed
escorts, who immediately gave chase. The swift companion easily outran them, enabling the Quedah to swoop in on
the merchantmen, now sitting ducks.
The latter Seventeenth century was a boom time for many other privateers, most notably Long Ben Avery and William Kidd.
That time proved brief, though, as the Anglo-French and Spanish peace treaties of Ryswick and Utrecht, in the early 1700s,
outlawed privateering. Dead Man Cay at Kingston, Jamaica, got its name for the convicted buccaneers left there in iron cages,
to “dry in the sun,” a euphemism for “become dead.” The iron bars were tightly fitted to their occupants’
bodies so that their bones remained in place long after the body had rotted away. 1701, when Captain Kidd was tried at Old
Bailey then hanged from the crude scaffolding at London’s Execution Dock, marked the end of the era of privateering.
Ezekiel Cooke, fresh from preying on a Portuguese barque, first learned of the Ryswick and Utrecht Treaties when English
officials hove to, boarded the Quedah and informed him that he’d been officially branded a criminal. They
had already commandeered his estate on St. Kitts and seized all of his possessions. They’d learned of his whereabouts
from Basil Hood, a privateer they’d arrested for, literally, pirating without a license. They subsequently let Hood
go, and fast, because his “pirate treasure” consisted of livestock that, unbeknownst to him, had been quarantined
because of a local malady which translates from Mayan as “Volcano of Vomit.”
Only by a sudden leap over the starboard rail and a four-hour swim through shark-infested waters did Ezekiel avoid “dancing
the hempen jig” from his own spars. He found safe haven on Barbados, and, a few weeks later, managed to import his
wife and six children. But like thousands of other privateers, he was suddenly out of work and broke.
To feed his family, the onetime great privateer captain resorted to “sucking rope” on a cocoa ship—and,
as merchants were suddenly taking advantage of the glut of seamen, he did so for a fraction of the wage common jack tars had
received a century earlier.
Not unrelated, shipboard conditions sunk to an all-time low. Rations were atrocious and rats outnumbered seamen ten-to-one
in the cramped, wet bunks. To men like Ezekiel, who’d made fortunes with official commissions to sail the seas and
plunder the ships of other nations, it hardly seemed reprehensible to reprise their fine work without a commission. The more
they rationalized it, the less distinction they saw between the lawfulness of privateering and the unlawfulness of piracy.
Ezekiel soon rallied a crew and, effectively, declared war on every nation. His story was not unique. Thus dawned the Golden
Age—from the pirates’ perspective—of piracy.
Far and away the most successful pirate of the Golden Age was Captain Bartholomew Roberts, who sailed onto the scene
in 1720. Having swiftly assembled a large fleet, he single-handedly devastated English commerce in Barbados and Jamaica for
years. When things got hot, he devastated the French instead. Roberts took four hundred ships, the Caribbean record. So
big a star was Roberts, he even had his own logo. Most pirates ships of the day flew the familiar skull and crossbones of
the Jolly Roger. Also popular was the all-red flag, which told sailors on targeted ships that their blood was about to flow
unless they hoisted their own white flag. Roberts’s brigs flew black flags bearing a cartoon of him toasting with Death.
In 1722, Roberts in fact met Death, in much less convivial circumstances: stray grapeshot during what proved his final raid.
Another luminary of the day was Edward Teach, known as Blackbeard, a moniker synonymous with terror thanks to a repertoire
of intimidation that included placing lit matches in his hair and beard so that it appeared to sailors whose ships he boarded
that his head was spouting fire. In 1995, a bearded man performed a similar stunt in New York City’s Washington Square
Park. People took him for insane and he was hauled off to Bellevue. In Blackbeard’s less media-savvy time, people
took him for Satan.
Like Roberts, Blackbeard also had his own flag. Something of a pirate flag hodgepodge, it was black, with a picture
of the Devil holding an hourglass in one hand while stabbing a heart to bloody bits with the other. Everybody told Blackbeard
they really liked it. Also like Roberts, Teach was struck down in his prime, the result of a swordfight in a North Carolina
barroom. In the last seconds before he died, Teach hoisted a glass and drank to the damnation of his adversaries. To this
day, Teach’s ghost is said to haunt the area. Not coincidentally, perhaps, most of those sightings have come after
visits to area barrooms.
While the demise of Roberts and Blackbeard was cheered by law-abiding sailors on their home seas, the pirates were mourned
in the soon-to-be United States. Caribbean pirates always received a warm reception in America, particularly the Carolinas
and New England, where godly Puritans were only too happy to take advantage of great deals on gold, jewels and cocoa.
In such safe havens, pirates banded together and, in effect, unionized. They created an organization known as the Brotherhood
of the Coast, which instilled a strong sense of honor among thieves, and, ironically, even legislated it, drafting a set of
guidelines known as the Pirate Articles. According to it, a pirate caught stealing from another could be marooned
on a deserted island with one day’s grace—a bit of food, a small bottle of water and a pistol. And that’s
if he were lucky. One pirate caught stealing a horse for meat was imprisoned, along with the horse, under the proviso that
he could go free only as soon as he’d eaten the entire horse.
At its apex, the Brotherhood had agents in various ports who not only brokered deals for their clients’ plunder,
but recruited personnel. The Brotherhood even offered its members vacation time, at St. Sugstin’s Bay in Madagascar.
St. Sugstin’s boasted the usual secret pirate hangout perks—beautiful women, other natural splendor, and plenty
of nooks and crannies to hide one’s brig—but it flourished as a pirate paradise like no other the world had seen
due, ironically, to the shopping. There, Brotherhood members could acquire the best and latest in pirate weapons, fashions,
accoutrements—like parrots—and flags. (Around that time, after much debate, the skull and crossbones was replaced
by the subtler but ultimately more blood-curdling black flag with a white silhouetted hourglass. When sailors saw it flying
from a pirate’s mast, it meant their time was running out.)
Lastly, the Brotherhood offered its members an Afterlife. Although they were viewed by everyone else in the world as
ruthless criminals beyond hope of salvation, pirates were inculcated with the notion that they could still maintain a course
for Providence, known as Fiddler’s Green. For this reason, in battle, Captain Roberts always wore a gold chain with
a large cross. Captain Daniel once stole a priest so as to celebrate Mass aboard his pirate ship. As it transpired, he shot
one of his crewmen for making an obscene gesture during the course of the service. In 1746, Ezekiel Cooke’s nephew
and piratical heir, Arthur Cooke, erected a life-sized gold crucifix at a monastery on St. Kitts. That the gold came from
a Spanish barque whose entire crew had been burned alive seemed to count less than the thought. The cross, incidentally,
was later stolen by Captain Daniel, who used a portion of the proceeds to build an orphanage.
As the Centuries turned Eighteen, pickings on the Main slimmed, resulting in piratic expansion to the Indian Ocean. Pirates
unwilling to relocate also faced beefed-up law enforcement. One of its leaders was missionary-turned-lawman François Malebarre’s
great-grandson, Captain Jean-Raphael Malebarre. Historians attribute his decision to enter law enforcement to the time Arthur
Cooke’s youngest son, Jeremiah, captured Jean-Raphael’s fiancée, Helena, during a raid on a passenger-bearing
merchantman. The kindhearted Jeremiah afterward sailed to Kingston and deposited Helena safely upon the shore of her family’s
estate. A few nights later, the smitten Helena stole a skiff and rowed back to Jeremiah’s sloop.
Jean-Raphael went on to pursue pirates with a fanaticism—and capability—previously unseen in the Caribbean.
Having effected a chain of communication which unified the disparate local governments, he successfully lobbied for the deployment
of more military might from Europe. At the height of his powers, men were hanged for as little as owning a parrot.
Consequently, as the centuries again turned, Caribbean piracy became populated by a bolder stock. Chief among them was
the ruthless (and, by pirate standards, that’s saying something) Jean Lafitte. Another of the period’s all-stars
was Arthur Cooke’s son Amos, the most audacious of a Cooke line known for its fearlessness. When the Governor of Hispaniola
offered a reward of 1,000 philips for his head, Amos responded with an offer of 10,000 philips for the Governor’s.
Asked once about the threat of his life ending in hanging, fast becoming a statistical likelihood for pirates, Amos said,
“The hanging’s no great hardship, for were it not for the threat of it, every cowardly fellow would turn pirate
and so infest the seas that men of courage would starve.”
By 1835, great numbers of the Brotherhood were indeed starving. Joint American and British efforts, with bigger and
swifter vessels, were all but eradicating piracy. A chief exception was the densely-packed cluster of islands south of Barbados
known as the Sugars. They varied in size from uninhabitable thimbles of rock to large tropical oases whose principal crop,
as one might guess, gave the range its name. As François Malebarre wrote in Catching Pyrats, “As surely as
spiders abound where there are nooks, so do pirates spring up wherever there is a nest of islands offering creeks and shallows,
headlands, rocks and reefs—facilities in short for lurking, for surprise, for attack, for escape.” The Sugars
proved a case study unrivaled in history. Old-fashioned, board-with-a-dagger-between-your-teeth piracy continued to flourish.
A second reason for piracy’s survival in the Sugars was that government officials of tiny commonwealths like Sugar
City, Maraca and Plantayne, motivated by personal financial enhancement, willingly—though unofficially—aided and
abetted local pirates. In 1854, the Governor of Sugar City received an annual income tax payment of 2,600 philips from a
local “conch fisherman.” It should be noted that, despite greater than 3000% inflation since 1854, the more successful
present day conch sellers earn only about 2,500 philips per annum. Another oddity therein is that the island of Sugar City
did not enact an annual income tax until 1904.
Government officials who didn’t benefit personally did so in other ways. For example, Plantayne’s mayor
turned a blind eye to the activities of pirate captain Moses Cooke, son of Amos. In exchange, Moses and his band acted as
Plantayne’s Navy, keeping away so-called “black ivory” traders such as Josiah Hood. Although he’d
never been more than a two-bit pirate, Hood amassed a considerable fortune in the slave trade. That fortune would have been
much more considerable if not for the interference of the Cookes. In the family tradition, Josiah Hood sought vengeance, commencing
an era in which the Hoods and Cookes were known as the floating Hatfields and McCoys.
In the years following the American Civil War, enhanced communication technology and the increased patrolling capabilities
of modern states reduced piracy worldwide to a trickle. By 1900, according to Royal Navy estimates, fewer than a thousand
earned their principal living in the pirate trade.
Intriguingly, pirate pride increased in inverse proportion to the drop in ranks. For the first time ever, the Brotherhood
published a newsletter (it was distributed covertly, of course). When Isaac Cooke was a boy—he was born, on Plantayne,
in 1937, the only child of “shrimper” Mordecai Cooke—he, like his friends, could recite the career highlights
of Kidd, Roberts or Teach the way boys farther north could rattle off the batting statistics of Ruth or Gehrig. Children
on Plantayne routinely played pirate, squabbling over who got to be Ezekiel, greatest of the Cookes, and who’d be stuck
with the roles of the loathsome Hoods.
After World War II, according to Royal Navy, the full-time pirate tally was estimated at four hundred globally, the same
as in 1563. Though exact numbers were unknown, the drop-off in Brotherhood members was much less precipitous in the Caribbean
than the rest of the world. Unlike their antecedents, these pirates kept a low profile. Earrings, bandannas, and swords
were reserved for private, Brotherhood-only functions—which were always extremely covert. Pirating runs were conducted
in fast boats disguised as merchantmen or fishing vessels. Raids were rapid, with pre-planned escape routes, and limited,
when possible, to victims who wouldn’t complain to the authorities afterwards, like Nazis sneaking to Argentina to escape
prosecution for war crimes.
Isaac’s first involvement in pirating anything larger than a langoustine trap was as a crewman, in May of 1949.
His uncle, Elihu, captained a heavily-motorized craft, disguised as a shrimping boat. They lay in ambush behind a small atoll
off Hamilton, Bermuda. Their target: the Concordia, a Swiss merchantmen shipping goods to Nazis on the lam. The
Concordia’s sailors outnumbered the pirates thirty to fifteen, and each Swiss was armed with a Mauser for exactly
such an occasion. Regardless, “there’s something about the sudden appearance of devilish men on your bow shouting
oaths and waving huge, curved swords that makes you drop your gun to the deck immediately so as not to put them to the trouble
of having to ask you to.” So the Concordia’s captain explained, a month later, when he and his crew
were found on the deserted island where the pirates had marooned them. The booty—vast stores of art and furniture and
thousands of silver ingots—meant Elihu Cooke and his crew didn’t need to go on any “shrimping runs”
for well over a year.
The circumstances were similar in Isaac’s first stint as a captain. He was eighteen, had a crew of just nine and
a slow, sail-powered schooner. But it took only a single theatrical cannon shot across the bow for their target, a Venezuelan
merchantman with eight times the crew and ten times the tonnage, to surrender. Unfortunately, the merchantman yielded just
a small amount of produce, having already delivered the bulk of its cargo to a port in Trinidad. Faced with the prospect
of cruising around in search of a black market for breadfruit, Isaac returned the ashen captain’s cargo in exchange
for a case of beer.
Isaac exhibited more of the cunning of his ancestors in his next gambit. It began when a Russian cargo frigate, Ivogor,
passing through the Lower Sugars en route to Buenos Aires, received an invitation, via carrier seagull, to a brothel on the
nearby island of Tangerine. The “sporting house,” as the note put it, offered “discounts to Russian gentlemen
and free vodka!” The majority of the Russian crewmen eagerly rowed to Tangerine that night, leaping from their longboats
as soon as they hit the beach, and galloping into the jungle toward the colorful lights. But they found no sporting house.
As they surmised at once, the lights were a decoy. By that time, though, the Ivogor was under weigh, Isaac and his worthies
having taken the skeleton crew in a minor skirmish and set them adrift.
Isaac sold the Ivogor in New Zealand and converted the proceeds into a veritable water rocket named the Virgil,
which he disguised as a tugboat. Over the next several years, he and a regular crew of a dozen worthies used her to prey
on merchantmen and smugglers in and around the Caribbean.
Similar operations were conducted, with varying degrees of success, by the more than nine hundred remaining members of
the Brethren (the Royal Navy had grossly underestimated) based in the Sugar Islands alone. A principle reason they escaped
notice was the hiring in 1952 of a smart public relations agent in New York, who attributed many captures, particularly those
which resulted in the disappearance of ships and sailors, to the “mysterious Bermuda Triangle.”
Piracy thus continued in the latter half of the Twentieth Century, and to this day, much as it had been in Bartholomew
Roberts’s day, just on a smaller scale.