The Cayman Islands: Where the Rich Get Richer

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The Cayman Islands: Where the Rich Get Richer

Explore the history, financial system, and future of the Cayman Islands, the Caribbean territory that became the global capital of offshore banking and tax-free wealth.

Simon WhistlerJuly.1.202654 min read

It’s the world leader in offshore finance, the place where the wealthy and well-off all across the globe squirrel away ungodly amounts of coin. It’s a question mark within the global economy, a place known for a government that doesn’t tell secrets, and doesn’t ask questions. Ever since they became a self-governing territory, the Cayman Islands have been the world’s premier tax haven. They’re a place in which the world’s rich and famous place the utmost trust, and where those on the outside will forever struggle to see through the veil.

But what are the Cayman Islands, really? From their centuries-old history, to the controversy and challenge of their recent past, to the future of these three little islands, we’ll explore just what makes the Cayman Islands what they are—and why they’re just as indispensable today, as they’ve ever been.

Caymans at a Glance

Embark on a voyage southward from the Florida Everglades, and you’ll be dodging land the entire way. You’ll risk running aground on the Bahamas and the Turks and Caicos Islands, just off the Miami coast. You’ll have to weave through the long island chain that runs from Cuba, to Haiti and the Dominican, to Puerto Rico, to the Virgin Islands, Montserrat, Barbados, and a long arc of other tiny island nations.

Key Takeaways

The Cayman Islands are a premier tax haven with a rich history of piracy and financial secrecy.
The islands’ economy relies heavily on tourism and offshore finance, attracting wealthy individuals and corporations.
The Caymans face significant threats from climate change, including rising sea levels and severe hurricanes.
Despite economic success, the Caymans struggle with issues like cost-of-living crises and social marginalization.
The islands’ future is uncertain due to environmental challenges and economic vulnerabilities.

But sail through the narrow pass between Cuba and Haiti, and then westward past Jamaica’s Montego Bay, and you’ll find the first of three long, skinny islands, known collectively as the Caymans. Built up from massive coral reefs, perched atop undersea mountains and sitting just alongside the six-thousand-meter, or twenty-thousand-foot-deep Cayman Trough, the archipelago is over a hundred miles from the nearest landmass, in the warm, gentle waters of the western Caribbean. The three islands are, themselves, separated by a significant stretch of sea, with the largest of them, Grand Cayman, sitting isolated from the twin islands Little Cayman and Cayman Brac.

Altogether, they comprise a land area of just 102 square miles or 264 square kilometers, roughly one and a half times the size of Washington, D.C. and barely one-sixth the size of the city of London.

They’re a place of incredible natural beauty, a tropical island paradise that boasts a stable, year-round summer heat, relatively little precipitation for most of the year, and warm seas that simply beg a swimmer to come and enjoy. Nearly totally flat except for a bluff on Cayman Brac, the islands have a grand total of zero rivers, and very few inland bodies of water. They boast scrub and evergreen forests in the inland areas, plus the largest inland mangrove swamp in the Caribbean, on Grand Cayman.

Mango, avocado, papaya, and a range of citrus fruits grow all across the islands, and a wide range of plant and animal species are well on their way to resurgence after a hard few centuries under colonial control. They are entirely without large animals, with their only native mammals being bats, and the only non-native wild mammals there being the Central American agouti. A range of herons, songbirds, and the Grand Cayman Parrot join the world’s smallest butterflies, the pygmy blue, flitting through the air.

The seashore is roamed by iguana, especially the green iguana, and for a person willing to look hard enough, small crocodiles called caimans lurk in the wetlands, joined by a small but rebounding population of American crocodile. The seas are overrun with marine life, everything from lively coral reefs to communities of beaked and sperm whale.

In terms of the human life on the islands, Grand Cayman is by far the busiest of the three, although even there, “busy” is something of a relative term. Home to roughly eighty-five thousand people, Grand Cayman is split into five districts, including the territorial capital of George Town, the largest city in all the British Overseas Territories. Some twenty-five hundred more people live on Cayman Brac, while a small handful of residents eke out a more isolated existence on Little Cayman—unless, of course, it’s Pirates Week, when the number of people on Little Cayman goes through the roof.

Despite their autonomy and their unique legal codes, the Cayman Islands are one of Britain’s sixteen non-self-governing territories, with its governor still appointed by the King of Britain and all the local parliament’s bills mandated to gain royal assent from the Crown. The territory brings in some five and a half billion dollars’ worth of GDP, they use their own Cayman Islands Dollar, and while a narrow majority of residents are of either a Caymanian or Jamaican background, the territory draws its population from every corner of the world. It’s a place where many families have lived for many generations, but where former high-ranking ministers have warned that its incredible population growth over the last decade will likely cause problems down the line.

The population is likely to reach 100,000 between the three islands, before the year 2030, riding a wave of former tourists who’ve chosen to look into a permanent stay.

And as a tourist destination, the Caymans are second to none. For vacationers and foreign expats alike, the Caymans offer unmatched, and exceptionally tranquil beaches, stretched around much of the three islands’ shores and washed in crystal-clear turquoise sea. They’re easily accessible from anywhere in the US state of Florida, even so close as to be affordable by way of a private jet, for travelers who would otherwise consider such luxuries beyond their means. Culturally diverse, with a well-earned reputation for the hospitality and kindness of the local population, the Caymans are near the top of most tropical destination lists. They boast luxury shops and extravagant hotels, a natural environment perfect for exploration and adventure. They’ve got some of the best underwater scuba and snorkeling attractions in the world, including a series of sandbars nicknamed Stingray City for their abundance of friendly rays, and a scuttled former US Navy ship that’s been transformed into an artificial reef. Visitors can even go to Hell, a one-of-a-kind limestone formation. All across the islands, the Caymans mix elegance, amenities, and natural beauty better than most places on Earth, helped along by the reality that the Cayman economy has little to work from, aside from tourism. The Caymans aren’t just a one-of-a-kind place to visit; they’d very much like people to come say hello.

But the Caymans weren’t always the vacationers’ wonderland they’ve become, and even today, that side of the island chain is just one part of a much larger story. In order to understand the Caymans at all, we’ve got to understand what happens below the surface—and to find the start of that story, we’ve got to head back in time.

Pirates’ Den

It’s widely assumed that the Cayman Islands were not occupied prior to their discovery by Europeans, or at least, not in any substantial way. To date, no archaeological evidence has ever emerged of settlements prior to the sixteenth century. It’s likely that the nearby Antillean Arawak-Taino tribes of modern-day Cuba, Hispaniola, and elsewhere would have visited the islands at some stage, given that they were adept mariners, and had long made a life hopping from island to island in great canoes. But those travelers either didn’t leave record of their presence, or have since had those records lost to history.

The question of the Caymans’ discovery by Europeans is somewhat in dispute. Per most accounts, Christopher Columbus is the one who gets credit for the find, not in his fated first voyage to the New World in 1492, but in his fourth trip on behalf of the Spanish Crown. The two ships under Columbus’ command, the Santiago de Palos and the La Capitana, sighted the chain’s two smaller islands on the tenth of May, 1503. Washed in turquoise waters that abounded with sea turtles, the two islands—today known as Little Cayman and Cayman Brac—were named “Las Tortugas.” Grand Cayman would go un-sighted for a while longer, and Columbus and his crew were unable to make a stop, with their ships already limping after damage by sea worms. But by the time Columbus laid eyes on the two lesser Caymans, Europe seemed to already have record of their existence, by unexplained means. In 1502, their presence was recorded on the Portuguese Cantino world map, and it’s likely that other Spanish sailors would have come upon them too, with several Spanish voyages sent to that area of the New World that hadn’t involved Columbus. Regardless, though, Columbus got the credit, and when Sir Francis Drake and his 23-ship fleet made a two-day stopover at Grand Cayman in 1586, they confirmed that that island, too, was uninhabited.

Not long after the Drake expedition stopped off in the Tortugas, the area became regarded as an easy source of vast quantities of meat for traders, explorers, slavers, and other European ships moving through the area. Very quickly after that, the population of turtles in the area was devastated, as well as the population of iguana and alligator, each prized for their value in protein for hungry and malnourished crews. About that time, the Cayman name began to be associated with the island chain too, as the place became regarded less for its turtles, and more for the sneaky little crocodiles that remained.

But through the mid-seventeenth century, the islands remained largely untouched in their inland regions, regarded as just another little curiosity in the Caribbean that not enough Europeans had yet arrived, to consider settling. Choked in suffocating swarms of mosquitos, and devoid of most resources, there was little there to make a stay worth somebody’s while. The first permanent inhabitant of the Caymans, one Isaac Bodden, wouldn’t be born there till 1661.

But by the 1660s, the Tortugas were under the control of a very different kind of settler: pirates, who had already chased away an expedition of settlers from the islands by that time. Preying on the ships that transited the valuable sea route, these pirates were able to loot all manner of colonial riches, be they mineral, plant, or, quite often, human. When, in 1670, the signing of the Treaty of Madrid between Spain and Great Britain granted the British possession of the Tortugas, the islands drifted into a strange and unique space in the Caribbean new order.

Although they were technically part of Britain, they were largely unclaimed and untouched, with few reputable Brits willing to work toward a settlement there. They sat right at the heart of Spain’s New World trade routes, funneling gold and silver from all across the American supercontinent to nearby Cuba. And while the British made sure not to embrace Caribbean pirates too closely, they were an invaluable part of the British Empire’s grand strategy in the Americas.

Pirates based in and around the Tortugas, drawing varying levels of support and tolerance from the Crown, had the effect of wearing down the Spanish empire by attrition, making it easier for Britain to gain relative power in the New World.

Although Port Royal, in modern-day Jamaica, and Nassau, in the Bahamas, would become far more developed as pirate towns during these years, the Caymans were sort of a forward outpost, a place where crews that sailed the high seas could make stops to re-stock on fruits and fresh water, hunt for or purchase turtle meat, and harvest as much wood as they could desire, to repair their ships mid-voyage. Hands-for-hire could often be found there, some dropped off by a ship after its crew disbanded, and others between jobs or looking to start work. Entire captured vessels could be manned and added to a pirate fleet by drawing on the manpower that waited there, or crew members who’d been lost to the waves or enemy cannon-fire could be replaced.

Not only that, but the crews’ knowledge of the Caymans allowed them to leverage the islands’ many hiding places to escape pursuers, and to conduct their repairs in relative peace. The settlements on Grand Cayman would occasionally be raided by the Spanish, but even these were relatively rare occurrences in the grand scheme.

Perhaps the most famous pirate who made the Caymans part of his regular hunting strategy, was one Edward Teach—better known today as Blackbeard. Although the island then known as New Providence, and its city of Nassau, was Blackbeard’s home base of sorts—along with a wide range of other famed pirates—the Caymans were a frequent stop on his journeys. After taking up with the renowned pirate Benjamin Hornigold, Teach became used to the lay of the Cayman shores, and after gaining command of a sloop of his own, the islands were a frequent stop in his raids around Havana. Although the Caymans were on the opposite side of the Cuban coast, they enabled Teach to attack from any direction he chose; come from the west and he could retreat to Nassau, but come from the east and he could round the tip of the greater island and retreat to Cayman Brac. Once Teach gained command of his own pirate fleet and gained his reputation as Blackbeard, his movements around the Caribbean became more of a matter of intrigue both in the area and back in Britain and the American colonies. After that time, he was known to have captured at least one ship in the vicinity of Grand Cayman, but more important than what we do know about his activities there, is what the other pirates of the time believed they knew. After Teach was killed in the Carolinas in late 1718, rumors spread among the pirates of the Caymans that he had hidden a treasure on Cayman Brac. If any such treasure did exist, and was ever found, then it’s not a matter of the historical record.

Nor was Teach the only renowned pirate that prowled those waters. Ned Lowe, an Englishman with a reputation for incredible brutality and torture on the high seas, made Grand Cayman his center of operations when he worked in service to the pirate captain George Lowther. Ned Lowe used the Caymans as a waystation in his travels, which saw him plunder as far north as Newfoundland and as far south as Brazil.

He’d be honored in the Caymans in 1975, by way of a postage stamp. The buccaneer Henry Morgan, who would eventually become Lieutenant Governor of Jamaica, would factor the Caymans into his long campaign against the settlements of Central and South America.

But the pirate age of the Caymans wouldn’t last too long after Blackbeard perished, with the islands’ population growing significantly enough by the 1730s that the Caymans were no longer an effective hideout. By that time, the pirate scourge of the American supercontinent was largely under control, or at the very least, in its dying years. According to some historians, the islands remained involved with the pirate legacy for a great deal longer. Long regarded as a sleepy backwater and a relatively safe outpost by the pirates of the day, it’s believed to have been the location of choice for many of them to live out their retirements, bringing with them the spoils of their plunder and helping to build a bigger settled economy in the area.

With that evolution, the Caymans became less and less of a frontier territory. Turtlers no longer had enough prey in the waters to sustain themselves there, and the people who had trickled in over the first century or so of its history began to really settle in. Some had been pirates, yes, but others had been refugees fleeing the Spanish Inquisition, others had been slaves who had found means to escape their bondage elsewhere, others were travelers and settlers from Europe who’d had to move on from difficult circumstances, and still more were formerly shipwrecked sailors who chose to remain, rather than seek a way home.

Even then, the islands were a highly diverse place, with Africans who had been brought to the Americas by the slave trade or born to those who’d been trafficked, and representatives of a wide range of European nations. Unlike most Caribbean settlements of the time, the Caymans seemed to be a place that was generally open to interracial unions and collaboration, and as generations went on, the Caymanians grew more and more comfortable on their little archipelago.

Quiet and Re-Emergence

The century that followed the end of the pirate age were a quiet hundred-or-so years on the Caymans, where although the islands were no longer a lawless place in the way they’d once been, they were still quite isolated from the outside world. Although they were, in effect, dependencies of the British territory of Jamaica, not many officials or visitors made the three-hundred-mile voyage from Kingston to Grand Cayman, and as such, the islanders were able to enjoy a great degree of latitude in managing their own affairs. An incident called the Wreck of the Ten Sail would make the islands famous in Britain for a time, after ten vessels in a trade convoy were wrecked on a reef eastward of Grand Cayman, and the Caymanian population braved the seas to rescue some 450 people with very few deaths.

According to some sources, an unidentified British royal was even onboard, and as a token of gratitude, King George III decreed that Caymanians would never be called to military service. Per Caymanian legend, this is also when the islands were established as tax havens, after the King decided that the islanders would never have a tax levied against them either. No Royal documentation of either claim has ever been procured, although the islands did, at some point, gain their status as a tax-free territory.

But the acclaim that the Wreck of the Ten Sail, and the subsequent rescue, brought to the Cayman Islands, was not followed by any great influx of new arrivals. Instead, the islands were able to do basically as they pleased in order to subsist, taking what advantage they could of the agriculturally productive land that their home had to offer. Other than subsistence farming, fishing, and turtling, the Caymanian population got by largely through salvaging, taking advantage of the frequent shipwrecks that were caused when the many local reefs proved too much for trade ships to overcome.

On more than one occasion, the Caymanians showed that salvage operations could have a dark side; this turned into a practice known as wrecking, in which Caymanians would use bonfires or strange objects to attract the curiosity of passing ships and lead them toward the shore. With most captains and navigators unaware of the reefs just under the surface, they’d be lured in and promptly wreck their ships, after which time the islanders would paddle out on canoes and plunder whatever they could. That practice, like the practice of piracy, became less common as the Caribbean became better settled.

As that part of the world grew more interconnected, it became far harder for a rogue handful of islands to avoid repercussions, but even without the settlers’ unique form of assistance, shipwrecks happened in ample numbers anyhow.

From the 1730s to the 1830s, slavery was in practice on Grand Cayman, although Little Cayman and Cayman Brac largely escaped the practice. In 1773, half the population of Grand Cayman were noted to be slaves, and in 1802, that figure was basically the same. In 1833, when the practice was abolished, the ratio remained basically unchanged. Because the Caymans were not suited to plantation agriculture, they never saw the level of slavery that other Caribbean islands did, like Jamaica, where at the time of emancipation, one free man resided per every ten slaves. On Grand Cayman, described author Gary Lee Roper in the book Antebellum Slavery, “There were no large plantations on the three small Cayman Islands, slaves were limited to the trades and domestic arts.” Many logged mahogany, and picked cotton in the short time that the industry avoided collapse, but those forms of work could not last long.

Also notable was the degree to which emancipation, in the Caymans, seemed to come relatively painlessly compared to most places. While across the Caribbean, former slaves were made ‘apprentices’ and saw a change in their circumstances only from horrifically bad to slightly less horrifically bad for the following several years, that process came and went far more quickly in the Caymans than elsewhere. Despite slaveowner resistance to British emancipation efforts, and a special resentment toward the peacekeeping infantry of Britain’s West India Regiment since the regiment enlisted black soldiers, emancipation was declared by Jamaica’s governor in 1835, and apprenticeships were ended not long after. After that, the former slaves on Grand Cayman began building their own settlements, and although the question of race relations was a difficult one for a time, the island’s reliance on the fishing industry would end up making the greatest change. With land industry even less feasible now than it had been previously, the Caymans were made reliant on fishing boats that relied on fair profit-sharing arrangements, and the relatively small community was forced into interreliance far quicker than it might have been, with a population ten times bigger or a landmass ten times larger. Slaveowners who had been resentful of the change to their circumstance, and who had even undermined attempts to educate the newly freed population, were forced to work together with their former slaves and their descendants or leave—and most chose to stay.

The following decades would see the Caymanians struggle not toward the great process of decolonization in the West Indies, but against it. Unlike the other islands of the Caribbean, the Caymanians were, by the mid-1860s, a pluralistic society that lacked any sort of cohesive, centuries-old cultural identity. From a pragmatic perspective, independence could have been a nightmare for the Caymans, owing to the possibility that it might be left on its own with no way to solicit essential support from places with actual natural resources and infrastructure. Making matters worse, they were becoming far less of a destination for seafarers, as the advent of the steam ship meant that sailors didn’t have nearly as much of a need to stop by and restock their wares. Amidst their pleas to maintain a British dependency, the Caymans were made part of the colony of Jamaica in 1863, although the degree to which they cared about being part of Jamaica appeared far greater than the degree to which Jamaica cared about having them along for the journey. As jobs grew more scarce and fishing catches grew leaner, Caymanians began to leave the islands as they grew into working age, headed to the United States, Nicaragua, and other nearby nations. But over time, those emigrants developed cultural traditions of eventual return, and leveraged the resources available to them abroad in order to send goods home. As the decades wore on, Caymanians were able to diversify their island economy in small ways, learning to beekeep and harvest phosphate fertilizer from the few and easily exhausted phosphate beds that existed there. But the influx of goods from abroad remained critical in keeping the islands afloat, and the idea that they might one day thrive, was for now out of the question.

Abroad, the reputation of the Caymanians had been a troubled one for some time, viewed with skepticism for the degree of racial mixing on the islands and for the relative obscurity of their lands and way of life. But as the nineteenth century gave way to the twentieth, that began to change. Reports on the Caymans became increasingly positive, noting crime rates so low that the main job of policemen was to ferry mail, and the combination of high religiosity—especially Protestant Christianity—and low alcohol consumption there.

Wrote one British researcher on the islands in 1927: “The Caymanian is of sterling stuff, self-reliant, not easily giving himself away, sober, dependable in any work he undertakes, and industrious. He is a home-lover and an excellent family man. As a sailor, he ranks with the men of Newfoundland and Bermuda […] It can safely be said that wherever he has gone the Caymanian has made a good citizen.”

From the perspective of the British, the Caymans were a ‘good colony’ so to speak—and rewards for good behavior slowly started to trickle in. When a fearsome hurricane ravaged the islands and killed over a hundred people, relief was slow to arrive, but once it did, everyone from the nearby British Jamaicans to dukes, colonial leaders, and even the King took interest in the reconstruction effort.

Over time, the British Jamaican governate became increasingly interested in helping the Caymans in setting up some degree of local governance, providing for a government-funded school system, local postage stamps and mail services, limited construction on Grand Cayman, and even their own Commissioner, who would hold governing power in the Caymans through 1962. They’d get a radio link and use it to make broadcasts to the rest of the world on what the Caymans were like, and they got significantly improved roads and town buildings that could double as hurricane shelters. The islands began to gain a reputation for building hand-made, high-quality ships, and built a culture around their master shipwrights, celebrating every new boat launch with an island-wide festival and a ceremony in which men, women, and children would haul ships together by rope into the sea.

During the World Wars, many Caymanians would travel overseas to fight and fewer would return home. A large subset would work for the British Merchant Navy, using their considerable seafaring abilities to ferry supplies, but those ships were just as dangerous as anyplace else in the wars, and during both affairs, the Cayman fighting-age population would lose many of its members. During World War II, two in three Caymanian men would take part in the war effort, greater than any other nation or territory of the entire war on the Allied side.

After the war, many Caymanians would continue to sail elsewhere, particularly on oil tankers. So common was it for Cayman residents to take their skills to the high seas that as late as the 1950s, the Caymanian government identified sailors as their primary export.

Eventually, the post-war decolonization movement of the 1960s made it to the Cayman islands, albeit indirectly. In 1962, Jamaica would gain its independence from Britain, and faced with the decision to remain a part of Jamaica, cast out on its own, or remain with Britain as a willful colony, the Caymans chose the latter. In the short term, it was a survival mechanism, the same as the decision to remain with Jamaica all those years ago.

The islands were no richer in resources during the 20th century than they had been during any other time, and with the turtle population gone, all the expensive luxury hardwoods deforested, and even the constant stream of shipwrecks finally done away with, the islands would have no real path to eke out an existence without British aid. It was either that, or watch family after family abandon the homes and communities they’d been part of for centuries, depopulating a tiny corner of the world that had only just gotten its start.

Becoming a Haven

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The Cayman Islands: Where the Rich Get Richer

But in their first few years as a direct British colony, the Caymanian population began to make a series of shifts that would eventually change their way of life. The islands had already started modernizing in the years after World War II, opening their first airfield, their first proper hospital, and their first commercial bank, a local branch of Barclays. A popular commercial dive center had opened up on Grand Cayman in 1957, by an accomplished diver named Bob Soto, and a handful of hotels had opened up relatively early on, as locals and global hospitality companies realized that this backwater colony was something of a vacation paradise.

Now, flights were stopping regularly at the international airport, sometimes as layovers but increasingly with the intent for their passengers to disembark and at last see the sights. Even cruise ships began to stop by at higher and higher rates, opening the possibility that a real tourist economy might be able to take shape—if, that is, the Caymanians were ready to facilitate it.

And as the people of the Caymans considered the future of their home, their attention shifted to the unique tax-exemption status they still enjoyed as a new, directly British colony. While the old story about King George III’s decree is likely a matter of myth instead of reality, the Caymans had still found their way to complete freedom from taxes, probably owing to the historical reality that with such a subsistence-based economy, there was very little on the Caymans to tax at all. In the years before and after the Caymans’ transition to direct British governance, the local government enacted a series of legislation backed by London, meant to structure a unique economy on the island that relied on, and even enshrined the lack of taxes. Rather than take money directly from residents, visitors, sales, or property acquisitions, the Caymanian government would levy duties on imports, sustaining itself on goods before they made their way into the territory and allowing commerce to flow freely from there.

With their tax law enshrined for the time being, the Caymans set about transforming themselves into an attractive destination for tourists and the finance industry alike. In 1959, the first written Caymanian constitution enshrined a woman’s right to vote; in 1965, the territory established the Mosquito Research Control Unit, which has since obliterated the vast majority of the Caymanian mosquito population. The islands got a Rotary Club, a weekly newspaper, a Chamber of Commerce, and even its own flagship airline, Cayman Airways.

By 1970, the Caymans had a total permanent population of over ten thousand, including many former residents who had spent the postwar years working abroad but now returned home to help reap the rewards of the new economic boom. Before long, this cycle became a feedback loop; the Caymanians were hard at work making themselves a more attractive destination, they thus attracted major international business, and international investors poured their own resources into transforming the islands even further. The capital of George Town, previously built as not much more than a large village, was expanded dramatically, and built not just outward but upward too.

In 1972, the Caymans ratified a new constitution, and introduced its own currency, the Cayman Islands Dollar or KYD. They opened themselves up to major global banks, and waited for the money to start pouring in. To be clear, they weren’t the only small territory around the world trying to make themselves into a financial hub for the modern era; Luxembourg was doing the same, the Bahamas were putting in an effort, so was Vanuatu, et cetera.

But the Caymans happened to be in the right place at the right time, in just the right ways for a compounding group of positive factors to attract more and more foreigners to their shores. The Caymans were a far better vacation destination than most places they competed with, and they attracted a broad range of investors who came for the beaches and the Mai Tais, and stayed for the business opportunity. They were a place with far fewer, or at least far less obvious social ills than many of the island nations they were competing with, and they had the veneer of continued British association to help them along.

They were a short journey from the United States, one of the world’s superpowers at that time, and they were the direct beneficiaries of a global trade system that still ran through the Caribbean.

By 1973, the Cayman banking boom was well-and-truly underway. Although the islands kept a strong preference for their status as a British dependency, they relinquished most forms of aid by the mid-seventies. Around that same time, the population had roughly doubled from what it had been just a few years ago, and even more business had come with the new arrivals. It makes somewhat less sense to try and detail the arrival of every bank, one at a time, than it does to simply show the end result: in the modern day, forty of the world’s fifty largest banks maintain branches in George Town, along with most of the biggest insurers and many major law firms. From not much more than zero percent in 1970, the financial industry now represents fifty-five percent of the Caymanian economy, and nearly half of all revenues pulled in by the government. One in three working Caymanians are employed in the financial sector, and well over one hundred thousand overseas firms maintain offices there—although we’ll be circling back to that, very soon.

As the financial industry attracted more and more high-profile visitors, the territory’s tourist industry worked hard to match. In the first year that the Caymans counted not just multi-day tourists but single-day tourists who arrived via cruise ships and other means, the islands counted over two million visitors. Those visitors enjoy beaches that the Caymanians had spent years refurbishing, cleaning up, and preparing for major foot traffic, and historical sites that have been preserved and rebuilt across the islands. Snorkeling and scuba have evolved massively since the early days of the practice on Grand Cayman, and the local wildlife has become well-accustomed to divers known for handing out snacks. Attractions like Pirates Week have become far more popular, created to round out tourism traffic in what was otherwise a slow season. Boutique, high-dollar hotels, shops, and restaurants have descended on the island, employing large portions of the Caymanian population in the process.

With the combination of global luxury tourism and high finance, the Caymans have created a unique symbiosis, feeding into Caymanian commerce with Caymanian tourism, and feeding into Caymanian tourism with Caymanian commerce. For the people who’ve called the islands home for many decades, or even many centuries, things are better, by far, than they’ve ever been. Grand Cayman has been thoroughly urbanized, and its reputation has grown beyond that of a natural paradise, into a sort of financial paradise as well.

All the while, the islands bucked off a few potential setbacks, dealing with an influx of thousands of asylum seekers from Cuba, and becoming the first Caribbean territory to establish offshore preserves to rescue and rehabilitate the dying local ecosystem. The National Trust for the Cayman Islands, established in 1987, has ensured the creation of everything from wildlife preserves to historic sites to a botanical garden named in honor of Queen Elizabeth II, who made her first visit in 1983.

But it’s important to understand that even amidst the islands’ broader renaissance, the Cayman transformation into the world’s leading tax haven was not a simple accident—albeit a happy one—for the islanders. In fact, the establishment of that side of the Cayman Islands was just as intentional as the rest of it, with perhaps even more myriad advantages in attracting people for whom the Caymans could be more than just a nice option to keep their wealth, and instead, the only reasonable option for people with any financial sense at all. During the 1990s, the Caymans established their Financial Services Supervision Department, their Monetary Authority, and their Stock Exchange, all the while establishing laws for national health insurance and pensions to ensure that the local population would be taken care of. Those rather bureaucratic-sounding institutions have gone on to become the safeguards of tremendous global wealth within the Caymans, and opened the door to a financial situation that is unlike any other on Earth.

How Do the Cayman Islands Work?

Before we can really understand what goes on inside the Caymanian financial system, we’ve got to understand what a tax haven really is. In some ways, the definition is simple; it’s a jurisdiction, be it a town, a city, a region, a country, or in this case, a territory, where a few key things happen at once. On the one hand, there need to be few or no taxes on things like personal wealth, personal income, sales, property…those sorts of things. The Caymans have that pretty well covered, although they used to impose a sales tax, which they’ve since dropped. Then, the taxes that do exist will typically have to avoid getting in the way of most foreigners and foreign businesses that operate there. In the Caymans, that’s done by taxing imported goods, but not levying any direct corporate taxes. Finally, the tax situation will typically be even better for a certain kind of person or organization, providing a route to access the best possible tax situation by taking a few extra steps. In the Caymans, that leads to a whole list of other tax breaks and conveniences for companies that register there, and for individuals, tax breaks get even better when they become residents.

With the Caymans checking all the boxes, and leveraging all those other assets like proximity to the US, allegiance to the British Crown, and the simultaneous success of the tourism industry, they became very attractive, very early, to companies that wanted to leverage its tax-haven status to make an offshore banking industry. By 1972, when the present Caymanian constitution was ratified, three thousand registered companies and another three hundred registered trusts had already established themselves there. At the time, that was roughly equivalent to one company or trust for every three actual Caymanian people, and it seemed as if that would be the Caymans’ primary focus in the offshore finance system. That is to say, they would have become a place where it was really easy and cheap to start and maintain a company, so lots of companies would have been started and based there. That’s proven true over time, and company formation and trust-holding are still important parts of the Caymanian finance system. By the 1990s, the island population of roughly thirty thousand was host to twenty-five thousand registered companies, meaning that even if the government decided to allocate, say, one company per citizen, even teenagers and older children would have had to start getting in on the game. But despite how major a factor company formation has been for the Caymans, offshore banking has become even more important over time.

The change began when the Bahamas became independent in 1973. Until that point, the Bahamas had been the place to go for offshore banking needs, but independence introduced instability in the financial system, and people who kept their money there became skeptical that the Bahamas would remain as open and hospitable for them as the islands had been in the past. Over in the Caymans, though, there was a legal framework for offshore banking that looked just like the one from the Bahamas, with enough infrastructure and enough commitment to remaining part of the UK that companies, banks, trusts, and large numbers of personnel made the move.

Once that process started, the Caymans never looked back; at the time of writing, the islands rank among the most utilized offshore banking hubs of the entire world, if not at the very top of the list. Yet of all the banks operating in the Caymans, only a small proportion have a physical presence there; the vast majority are simply there for the perks of association.

Of course, simply discussing the presence of offshore banking in the Caymans doesn’t really do justice to what offshore banking really is. Beyond just the thing implied in its name—banking, except it happens outside a person or organization’s home nation—it’s a complex process that offers major benefits to international corporations. For one thing, money or other assets held offshore often aren’t subject to tax, or at least not in the same way as they would be if held in one’s own country. Not only that, but holding money in foreign bank accounts can offer increased security and shield a person from economic volatility at home, while converting that money into a foreign currency allows it to be more easily used in trade and kept safe from things like inflation in the currency of a home nation. Finally, there’s the element of secrecy; the Caymans, and a range of other offshore havens, know where their bread is buttered, and privacy laws around bank account information are kept very, very strict in order to build confidence among foreigners. The territory has attracted a wide range of top-tier asset managers, tax planners, legal experts, and investment services, making them not just a place to store wealth, but a place where that wealth will be very well-taken-care-of.

But with the basic structure of offshore banking, also comes major potential for these banks to be used in ways that many nations consider illegal. Depending on what a person or corporation is up to, that might include hiding away one’s personal wealth in a way that keeps it a secret from one’s own nation. It might include hiding money that’s obtained through illicit means, like fraud, drug trafficking, embezzlement, or anything else. And it might even include money laundering, the practice of transferring illegally obtained money through a series of legitimate-looking financial pathways in order to hide its true origin. And sometimes, it’s a simple matter of tax evasion. In the United States, by example, holding money offshore is perfectly legal, but it’s all got to be disclosed to the Internal Revenue Service, even if it’s made internationally by a US citizen or corporation. Holding money abroad is legal; hiding money abroad is not. And according to not just the US, but many other world nations, even money that happens to be held abroad is still taxable. It’s still your money, and you’re still a citizen; by their logic, the place your money is stored shouldn’t matter much.

In the Caymans and other, similar spots, though, the path to hiding one’s ill-gotten gains has, at certain points in the islands’ history, been a good bit easier. For a very long time, Caymanian authorities have emphasized client privacy to the extreme, in policies that, we should be clear, are highly sought-after for all manner of legitimate business. But as the Caymans and the banks there have not had a burden of responsibility to establish the source of the funds transferred in, they’re subject to a handy blind spot that can see illicitly acquired cash and assets funneled into tightly guarded vaults that are nearly impenetrable from the outside world.

Such a turn of events may not be the intended by-product of the Caymanian system, and certainly, the last several years have seen rigorous efforts by the Caymans to tamp down on such behaviors. But even still, historically lax oversight has its perks for those looking to get away with something shady. According to a United States assessment by the Bureau of International Narcotics and Law Enforcement Affairs, published in 2014: “Most money laundering that occurs in the Cayman Islands is primarily related to fraud and drug trafficking.

Due to its status as a zero-tax regime, the Cayman Islands is also considered attractive to those seeking to evade taxes in their home jurisdictions.”

And the Caymans are also perfect for other practices that, while not necessarily illegal, still raise a whole lot of eyebrows. One such practice is the establishment of shell corporations, offshore companies that a corporation, a person, or some other business entity might establish for a few key reasons. To use one example, a US company that earns a profit is subject to US corporate taxes; in 2023, that tax rate was 21% on the profits they earn.

But if that company sets up a shell corp in the Cayman Islands, where that tax rate is zero percent, they don’t have to pay anything—even while still declaring their income to the IRS. Sure, if that shell company then provides, let’s say, the money to pay US-based executives, that income will still be taxed. But rather than get paid all their money up-front, those executives can keep most of their pay offshore in those Cayman bank accounts, eventually retire, and just move to the islands to claim it at a zero-percent tax rate.

Of course, that’s just one example, but the others tend to lead to similar, tax-free results no matter how you get there.

Of course, simply building a system that offers real benefits to all wealth-holders, like the Caymanian tax-free system, isn’t an invitation to leverage those systems for criminal purposes. Yet in practice, money hidden away in offshore accounts typically isn’t going to be disclosed to other world governments if the account-holder doesn’t disclose it themselves, and banks in the Caymans have built one hell of a reputation over time for their discretion. Britain, historically, hasn’t stepped into Cayman affairs unless absolutely necessary. Add to that, that in the decades when the Caymanian system was coming into its own, the islands suffered from a combination of financial regulations that were still getting their bugs worked out, and a pragmatic legal system that seemed to understand—allegedly—that finding more clients to stabilize the Cayman economy was of higher priority than screening those potential clients for a role in illicit industry. Even as recently as 2020, a study by the Tax Justice Network found that the Cayman Islands were still the world’s most prominent hub for global financial secrecy, enabling tax abuse, corruption, and money-laundering. The Caymanian government will insist—and, in recent years, has insisted—that it faces, and battles against, a legion of international enemies trying to abuse its financial system. But as for how hard it’s fighting that battle…well, let’s defer to Transparency International, alleging in 2017 that the Cayman’s Financial Crimes Unit employs a grand total of eighteen staff, tasked with investigating a mountain of wealth roughly equivalent to the size of Russia’s economy.

When it comes to global financial scandals, the Caymans have dodged some, and been implicated fairly significantly in others. When, in 2016, a treasure trove of eleven and a half million finance-related documents called the Panama Papers were published for the world to see, the Caymans were only involved in a relatively small subset of the financial dealings they revealed. Switzerland, Cyprus, the Virgin Islands, and, of course, Panama took the bulk of the hits, although the Caymans were wrapped into broader financial reforms that Britain imposed on its overseas territories—much to the consternation of Caymanians. So, too, did 2021’s release of the 12-million-file Pandora Papers largely miss the Caymans with the most serious revelations, despite the islands being mentioned throughout. But in 2017, an info-dump called the Paradise Papers wrapped in the Caymans a good deal more. In those releases, the Queen of England’s private estate was revealed to be using a Cayman fund to exert indirect control over a company called BrightHouse, which sold British people household goods via payment plans with incredibly high interest rates. A close adviser to Canadian PM Justin Trudeau was found to have moved millions of dollars into a Cayman trust, likely dodging taxes in at least three different countries including Canada, while America president Donald Trump’s then-commerce secretary was found to be using several Cayman accounts to maintain a stake in a shipping company that did big business with a prominent Russian energy firm part-owned by Vladimir Putin’s son-in-law. Those leaks implicated over eight thousand individuals or organizations with Cayman addresses. And with leaks, frequently come accusations; one famous instance of rather well-founded finger-pointing came from then-candidate Barack Obama in 2008. Spotlighting a five-story building in the Caymanian capital of George Town, he said: “You’ve got a building in the Cayman Islands that supposedly houses 12,000 corporations. That’s either the biggest building or the biggest tax scam on record.” Those corporations, by the way, included Coca-Cola, General Motors, FedEx, Intel, and many other major international names. And while Obama had a good point back then, he didn’t know the half of it. In 2021, Ugland House was the registered office address for a full forty thousand companies, including major international investment funds and global business ventures—and that’s according to the house’s own explainer web-page, in an overview designed to explain why there’s no cause for concern.

Over the last few years, the financial situation in the Caymans has changed somewhat. Today, the islands hold about three quarters of all the hedge funds in the world, plus several billion dollars in disclosed deposits. Already rolling in the dough, the Caymans have come a long way from the commerce-desperate, secluded islands they used to be, and now, the islands are much more at liberty to say no to potential customers they believe to be engaged in anything untoward.

Compliance laws and enforcement in the Caymans have grown stricter and stricter as time has gone on, and the vast majority of the money coming into the Caymans now is believed to be clean. That money is spoken-for by trustworthy companies and brokers, and it can resist stringent cross-checks without fear of being snatched away after investigations. And now more than ever, the Caymans are at liberty to charge high banking fees for those looking to store wealth or incorporate companies.

When it comes to price, Belize and the Seychelles are the budget options in the 2020s, and the Emirates and Hong Kong are significantly more affordable choices as well. The Cayman Islands aren’t just a small player anymore; they run the game, and with the world of offshore finance now dominated by the three little islands south of Cuba, they can afford to be far more discerning in their clientele.

Yet, we must emphasize again, many expert financial organizations around the world simply don’t agree. The 2020 Tax Justice Network study we referenced earlier provided documentation showing that the Caymans had been blacklisted by the finance ministers of the European Union as a tax haven, and alleged that the Caymans now host over a hundred thousand companies—more companies, at that time, than people. The study, and others like it, make assertions that run directly contrary to the Caymanian government’s claims—that it cooperates with nations around the world, and has implemented meaningful transparency measures. In 2017, the prominent NGO Transparency International summed it up best with a headline on the tax haven: “Who doesn’t know the Cayman Islands is a great place to hide money? The Cayman Islands.”

The Caymans Today and Tomorrow

In the modern day, the Caymans’ improved standards for responsible offshore banking have still left some to be desired, but on balance, the situation is still a good deal better than it once was. High-revenue business still has much to gain from leveraging the Cayman system, and certainly, the islands have struggled to shed their global reputation as a nexus for dark money. Yet at least for the time being, the Caymans’ place as a leader in global finance is secure—leaving the territory’s leaders to turn their attention to the myriad other issues the Caymans have to deal with.

Unfortunately for the territory and its residents, the Caymans’ high standard of living and its global repute as a dream destination have not been enough to stamp out a range of significant problems, present and future. Perhaps the greatest among those problems, and among the least affected by buckets of Caymanian cash, are hurricanes. The storms are very, very common for much of the year in the Caribbean, and they strike the Caymans more frequently than nearly anywhere else in the Atlantic. Because hurricanes form southerly of the Caymans and tend to travel quite often in their direction, the islands frequently find themselves in the line of fire, but even worse, they’re entirely exposed. Unlike other landmasses, the Caymans don’t have the benefit of other islands that a hurricane would have to pass over first, thus taking some of the edge off.

In the last few decades, Hurricane Ivan was the worst of all. A Category 4 hurricane with sustained winds of 155 miles per hour, the eye of the storm, in Ivan’s case, didn’t hit the Caymans head-on, but it caught a hell of a shellacking anyhow. For some seven hours, the Caymans withstood winds in excess of a hundred miles per hour, and in the worst minutes, those winds accelerated to a sustained 150 miles per hour, with peak gusts passing north of 170.

Grand Cayman was completely overswept by a storm surge of some eight to ten feet, submerging everything except the island’s northeast corner, and dumping an additional foot, 308 millimeters, of rainwater. Although only a small proportion of dwellings on Grand Cayman were completely wiped out, seventy percent were severely damaged. Two people died, over four hundred were injured, power and water were knocked out for months, and the Caymans withstood damages of over five billion dollars, nearly two years’ worth of GDP.

In that case, the Caymans were able to build back within about two years to pre-hurricane status, and although 2001 saw another highly costly storm, the islands are typically at least somewhat lucky; depending on where the hurricanes form, they might wash over the Caymans before they really pick up steam. Not only that, but the Caymanian government is well aware of the threat that hurricanes pose, and the territory’s wind-resistant buildings and well-practiced anti-hurricane measures have gone a long way to save lives. In the years to come, the Caymans may not be so lucky; climate experts widely expect that hurricanes will continue to grow worse, year over year, and the next hurricane to land a direct hit on the Caymans may do far worse than what Ivan did.

More broadly, climate change is among the most critical threats facing the Caymans. A British report published in 2023 found that the Caymans face severe climate risks in no fewer than eighteen areas, everything from devastation of coastal settlements due to rising waters, to the destruction of key infrastructure like sewage and road systems, to mass die-offs in the coral reefs around the islands. By the year 2050, just twenty-five-odd years away at the time of writing, up to a third of the Caymanian landmass could be fully and permanently underwater, with high tide washing over significantly more of the islands.

While the Caymans are three islands now, they won’t be by then; instead, the landmass known as Grand Cayman will be carved up into dozens of little islets, and the famed beaches that the Caymans are known for today, will be long gone by that time. For the Caymans, that’s not just an issue of displacement to the local population; instead, it risks disruption of the islands’ entire practice of providing residency to well-off foreigners, and will almost assuredly destroy much, if not all, of the tourist industry.

And even for the few decades in which Caymanian tourism will still be viable, it’s not nearly a stable enough industry to be relied on, year after year. That’s something the Caymans learned firsthand in 2020 and 2021, when global shutdowns amidst the COVID pandemic put a halt to the vast majority of foreign travel. The Caymans, like much of the world, closed up shop for a span of years, and as a result, tourism went down close to zero.

The Caymanian GDP shrank by five percent in 2020, matching only the impact of the 2008 financial crisis—and when we mention the financial crisis, we touch on another reason why the Caymans are so vulnerable. For a place that relies on tourism for seventy percent of its GDP and three quarters of its foreign-currency earnings, the next global shutdown, the next stock market crash, and the next disruption of a sort we can’t foresee as easily, risks delivering another massive blow. Sustain that economic deprivation for two years, or three, or four, and the Cayman economy has little means to survive.

If all that sounds bad enough, then we’ve got to deliver a major let-down, in the form of even more trouble. Over the past few years, the Caymans have sunk into a major cost-of-living crisis, brought on by record levels of inflation over the last few years. While figures have calmed down significantly by early 2024, a period of significant economic shock continues to have consequences for businesses on the islands, but especially for individuals and families that don’t enjoy the same wealth as the islands’ rich and famous. The price of essentials, from housing to fuel to food, have raised significantly in the past several years, and the islands’ public utilities are an increasing financial drain for anyone who can put a roof over their head. At the same time, wages have not kept pace, meaning that not only have ordinary Caymanians had to pay out more money, but they’ve had to do that while having significantly less to spare. Because the Caymans are so proximally dependent on the United States, they’re economically dependent too, especially for food imports—and with rising food costs in America, the situation in the Caymans just gets worse, and deteriorates faster, than it does stateside. In yet another compounding factor, the exceptionally low birth rate on the Caymans and the high proportion of new immigrants age sixty-five and older mean that workers, just like food, have to be imported from abroad. More competition from foreigners means both less housing, and fewer job opportunities for Caymanians, and as jobs and housing disappear, poverty, homelessness, and desperate emigration follow close behind. According to some Caymanian former officials, the island infrastructure and service industry will most likely falter even before the climate does, condemning the Caymans to the first phases of collapse even while its boulevards and beaches remain dry.

Snap your fingers, make all those problems go away in the Caymans tomorrow…and the territory will still have work to do. In just one example, the Caymans have criminalized the practice of obeah through the 2020s. Obeah is a broad term, encompassing a range of religious and healing traditions practiced by the African diaspora across the Caribbean, and their practice today on the Caymans traces its long and painful history to the Atlantic slave trade.

Laws against obeah have survived across the Caribbean, including in the Caymans, despite clearly enshrined rights to religious freedom, and while the issue has recently been addressed in a legal sense, Caymanian stigma against obeah will take far longer to dismantle. Elsewhere on the islands, social marginalization of non-English-speakers, a lagging minimum wage, and a subset of the population still living without power or running water all contribute to the islands’ issues, while the weight of money-laundering and tax-evasion accusations still weigh them down.

So on the one hand, the Caymans today are far richer than they’ve been for the vast majority of their history. They’re known the world over for the financial services they provide, and they’re a sought-after, even exalted vacation destination. But staring down the barrel of changes beyond the Caymans’ ability to stop, and facing an increasingly heavy crush of problems at home, it’s become crystal-clear that the best days of the Cayman Islands are either already behind them, or soon to pass.

In fifty years’ time, there may no longer be any land known as the Cayman Islands, or if there is, it’ll be that little bluff on Cayman Brac, quite possibly playing host to one single building that hosts several hundreds of thousands of international corporations. What happens to the rest of the islands, is already transparently obvious; what happens to the people there, is as-yet unknown.

If there’s anything that isn’t likely to change on the Caymans, it’s the islands’ status as a British territory, and it’s that status that may offer Caymanians their final lifeline. Conversations on leaving the protection of the Crown, and going independent, receive just as forceful push-back today as they ever have, shouted down by Cayman residents who know all too well that even if things held steady, much of the territory’s success ties directly back to the legitimacy and trust its British governors afford it. And come a time when the Caymans are no longer so stable—or, indeed, when they might not even be habitable—saying goodbye to that British territorial status today, could leave the Caymans completely without options tomorrow.

For the islands’ younger population, who will one day almost certainly watch their islands and their community sink below the waves, Great Britain might be the place they eventually call home. After all…what other options are there?

Presented by

Simon Whistler

Simon Whistler is one of YouTube's most prolific educational creators, with tens of millions of subscribers across his channels. Places is his expedition into the world's most remarkable locations — from cities carved from salt to islands nobody dares inhabit. He brings a researcher's rigour and a traveller's awe to every field note.

Frequently Asked Questions

What is the Cayman Islands’ primary economic activity?

The Cayman Islands’ primary economic activities are offshore finance and tourism. The islands are the world leader in offshore finance, attracting wealthy individuals and corporations to store wealth and establish companies due to their tax-haven status. Tourism is also significant, with the islands offering luxurious beaches, scuba diving, and other attractions.

How many islands make up the Cayman Islands?

The Cayman Islands consist of three islands: Grand Cayman, Little Cayman, and Cayman Brac.

What is the capital of the Cayman Islands?

The capital of the Cayman Islands is George Town, located on Grand Cayman.

What is the population of the Cayman Islands?

As of the information provided, the population of the Cayman Islands is approximately 85,000 people, with the majority residing on Grand Cayman.

What is the official currency of the Cayman Islands?

The official currency of the Cayman Islands is the Cayman Islands Dollar (KYD).

What are some of the unique wildlife found in the Cayman Islands?

The Cayman Islands are home to a variety of unique wildlife, including the Grand Cayman Parrot, the pygmy blue butterfly, green iguanas, and small crocodiles called caimans. The seas around the islands are rich in marine life, including coral reefs and various species of whales.

What is the historical significance of the Wreck of the Ten Sail?

The Wreck of the Ten Sail is an incident where ten vessels in a trade convoy were wrecked on a reef eastward of Grand Cayman. The Caymanian population braved the seas to rescue over 450 people, leading to a decree by King George III that Caymanians would never be called to military service or have a tax levied against them, although no official documentation supports this claim.

What role did the Cayman Islands play during the pirate age?

During the pirate age, the Cayman Islands served as a hideout and supply station for pirates. Famous pirates like Blackbeard and Ned Lowe used the islands to restock and repair their ships. The islands were also a place where retired pirates settled, bringing with them the spoils of their plunder.

What is the significance of the Financial Services Supervision Department in the Cayman Islands?

The Financial Services Supervision Department in the Cayman Islands is responsible for overseeing the financial system, ensuring that it remains a safe and attractive destination for offshore banking and financial services. This department, along with the Monetary Authority and the Stock Exchange, plays a crucial role in maintaining the islands’ status as a leading tax haven.

What are some of the environmental challenges facing the Cayman Islands?

The Cayman Islands face significant environmental challenges, including the threat of hurricanes, rising sea levels due to climate change, and the potential loss of their famous beaches. By 2050, up to a third of the Caymanian landmass could be underwater, posing a severe risk to the islands’ tourism industry and residential areas.

Sources

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