As the advertising images on the Internet and in glossy magazines remind us, the contemporary image of Bermuda is of a beautiful semi-tropical paradise that one never wants to leave. Full disclosure: Back home, following my first visit to the Rock, on dismal Canadian winter days I used to fantasise about mailing myself back to Bermuda—but wait, how many stamps would I have to paste on my forehead to get through the post? (Turns out, ironically, that the postage was more or less equivalent to the air fare.) Others dream: if only I could hide away on a ship in New York and sail away into the Sound…ah, a romantic image of stowaways worthy of the exciting novels of Robert Louis Stevenson.

By contrast, what is jarring is a long and very real history in Bermuda of stowaways secreting themselves on vessels to get off the Rock, not onto it. There is a varied and often melancholy—but always dramatic—backstory to such stowaway tales. The hideaways are from the ranks of the Rock Unhappy, one might say—those willing to break the law (for stowing away is a criminal offence) to get away from the island. In fact, the topic of stowing away out of Bermuda has featured in the international media recently, the New York Times included—all because of the death in 2016, at a ripe old age, of a distinguished New York lawyer, who in his youth had had fifteen minutes of fame as the most famous child stowaway of the 1930s.

Newspaper readers in North America, Bermuda and the United Kingdom were reminded in the recent news obituary of a tale that had everything—wealth, glamour, patriotism, intrigue and a seemingly happy ending. But the full story is darker, prompting us to realise that Bermuda can be a site of sorrow, despair and injustice as well as a bucolic “nature’s fairyland.” That proves to be the case whether the individuals involved (a varied cast of surreptitious escapees, chief among them) are unhappy expat children, fugitives from slavery, murderers trying to cover their tracks, sinister prisoners of war hightailing it out of captivity, or underemployed black Bermudians seeking a better life.

First, let us consider the case of the boy stowaway of Jazz Age Bermuda who hit the papers again last year—Carroll Wainwright Jr., nine years old in 1934, an economically privileged great-grandson of the American railway robber baron Jay Gould, and stepson of a Scottish shipping magnate, Sir Hector MacNeal. In the wake of the development of Tucker’s Town in the 1920s and of the Prohibition era in the United States, Bermuda attracted rich, pleasure-loving visitors who cherished the island’s golf, gin, bathing, bridge and mild climate as they mingled with their own kind at the likes of the Mid Ocean Golf Club and the Hamilton Princess and Castle Harbour hotels. Both Carroll’s stepfather and his mother, American tabloid darling Edith Gould Wainwright, now Lady MacNeal, were regular visitors to Bermuda.

For Carroll’s glamorous mother, whose gilded but troubled lifestyle had long been a staple of the popular press in the age of yellow journalism, the Rock usually meant relief from the glare of the kind of publicity we now call celebrity journalism. In 1934, ordinary Americans caught in the grip of a brutal depression fantasised about the gilded few, whose problems, while real, were anything but financial—for example, Gloria Vanderbilt, dubbed the “poor little rich girl,” the centre of a transatlantic custody battle during the Depression, or the tragic Lindbergh baby, kidnapped from his crib by night in 1932 from the New Jersey mansion of Charles and Anne Morrow Lindbergh, his famous aviator parents, only to be dropped to his death from a rickety ladder during the abduction.

For her part, Lady MacNeal, nee Edith Kingdon Gould—formerly Mrs. Carroll Livingston Wainwright—had been titillating New York and Philadelphia society gossip columns for nearly two decades. Born on board her father’s yacht in 1900 and an heiress to what the papers described as “a dazzling heap of the Gould millions,” she first hit the American popular press in a big way when she eloped at the age of 16 with another scion of wealth, just one day after graduating from her tony New York finishing school. She had met 21-year-old art student Carroll Wainwright at a house party a few months before. Two sons and a daughter later (Carroll, the youngest, was born on the floor of his mother’s Pierce-Arrow limousine en route to the hospital), Edith moved to Reno in January 1932 to secure a quickie divorce.

Marital life at the top had been no paradise: allegedly subject to mental breakdowns, her talented young husband had been in and out of psychiatric facilities, stays which embroiled him in lawsuits over his involuntary committal (which he ultimately won in 1932) with his Wainwright siblings. A few hours after the Reno divorce from the now-discharged Carroll was granted on the grounds of mental cruelty, Edith, amid the popping of flashbulbs, promptly wed Sir Hector Murray MacNeal, a Scottish shipping millionaire a quarter-century her senior who had been knighted during the Great War for services to the British war effort.

Fast forward to Hamilton Harbour on the eve of American Thanksgiving, 1934. Lady MacNeal and Sir Hector, peripatetic travellers, were sojourning in Bermuda, with two of her children in tow. Nine-year-old Carroll had been enrolled in Saltus upon the family’s arrival some three weeks earlier. But he was having none of it. In school uniform, he rode his bike down to the harbour one November afternoon just before the American holiday and simply walked aboard the liner Queen of Bermuda, just about to sail for New York. Who, after all, was likely to challenge a privileged white visitor lad among the throngs of the well-heeled white folks going up the gangplank, when the boy stoutly declared to the crew that his relatives were already aboard and that he wanted to wish them bon voyage?

Dockside security was lax in those days. Bermuda officials were more interested in vetting those arriving in Bermuda, rather than those sailing out of port. Not until the ship was well out at sea, did young Carroll, now hungry for dinner, emerge from the first-class cabin where he had hidden to tell a steward what he had done. He declared that he had stowed away in order to go back to his paternal grandmother’s in New York for Thanksgiving and to attend an all-American boys’ school like his brother’s.


Young stowaway Carroll Wainwright Jr. and the Queen of Bermuda – the ship he so boldly stowed away on to return to the US without his mother’s permission


Meanwhile, back in Bermuda, there was consternation over the missing boy—was this another Lindbergh kidnapping? The police were called in by his frantic mother well before the Queen radioed back to Bermuda that the “bright, sturdy lad” (as the captain described him) was aboard and safe. The Bermuda and international press had a field day—Carroll was depicted as a kind of Jazz Age Huckleberry Finn, a fearless, true-blue, little Yankee adventurer who had simply wanted to get back to the turkey and pumpkin pie of a big, extended-family American Thanksgiving, a holiday not observed on the Rock. The papers dubbed him “The Silk-Stockinged Stowaway.” The headlines insisted that “He Was Game To Be A Huck Finn—But Not A Little Lord Fauntleroy.” His paternal grandmother met him in New York, assured him that she was “not mad” at him when he plaintively asked, and retroactively paid his passage (first class). Trying to dodge all the reporters, she whisked him off to her big estate to ready him for enrolment in an American boarding school, an arrangement already in place for his older brother, Stuyvesant. Lady MacNeal, avid readers were assured, intended to sail shortly for New York, to be speedily reunited with her adventurous son.

If only that were the whole story. Research uncovers hints of a sadder tale. The Royal Gazette society columns in the aftermath of the incident record frequent solo appearances at golf and bridge tournaments by Sir Hector—yet only in January, months after young Carroll stowed away, do we read that Lady MacNeal was finally sailing back to New York to see her son. But when she did arrive in New York, she was in a state of collapse. An ambulance was needed to take her from the pier to her home. Three years later, with Sir Hector apparently occupied elsewhere, Lady MacNeal died on her Long Island estate at the age of 36. The reported cause of death? Alcohol-precipitated liver disease. Her considerable estate (over 1.5 million dollars, a fortune in those days) was divided among her three orphaned children, who were still being overseen by their grandmother—not their father. All in all, this stowaway story no longer smacks of the antics of Mark Twain’s Huckleberry Finn; instead, it is shot through with sadness and excess out of an F. Scott Fitzgerald novel.

Carroll Wainwright never returned to Bermuda, despite a long family tradition of holidaying there—and no wonder. No sentimental memories here. This stowaway saga suggests the sad fact that the life of the international rich who come to Bermuda is at times no fairy tale. To underline the lesson, we know that there was yet another young, upper-class American stowaway on the Queen of Bermuda that day—16-year-old William Hines, whose family fortune was made in root beer.

It is not only moneyed expats who have stowed away to get off the Rock, however. Earlier, those caught in the era of slavery in Bermuda sought another kind of transformation—from captivity to freedom. In fact, throughout Bermuda’s history, slaves, spies, the un- and under-employed and others have attempted to leave by ship and by stealth. In Chained on the Rock, his pioneering history of slavery in Bermuda, historian Cyril Packwood wrote that Bermuda slaves, who were often skilled sailors, looked to sneaking aboard departing vessels, especially out of St George’s, as one way to find freedom. Not an easy feat, given the relative smallness of most sailing vessels in the seventeenth, eighteenth and early nineteenth centuries and the pangs of hunger that would soon assail a stowaway—as would fears of reprisals against the slave families left behind. Advertisements, Packwood tells us, warned foreign captains not to employ runaways as crewmen. Even after Emancipation in 1834, during the 1879 Skeeters murder case, the soon-to-be-convicted murderer, Edward Skeeters, initially claimed that his victim, his wife Anna, long known to many as a battered woman, had stowed away on the famous Bermuda sailing vessel, the Eliza Barrs, which had just left port, to escape her troubled marriage. Fisherman Skeeters had in fact stowed Anna’s battered corpse on the ocean floor off their waterside Somerset cottage with the aid of a large rock.


The Eliza Barss, painted by Stephen J. Card


One fabled stowaway was also a sinister (if superficially charming) psychopath. In the early 1900s, at a time when thousands of Boer War prisoners captured in the hostilities in South Africa between the British and the defiant Boer settlers there were held captive on islands in Hamilton Harbour, one particularly devious prisoner did escape. The Boer War had formally ended in June 1902, but Boer prisoners were forbidden to leave Bermuda and return to the far-off colony in South Africa without first swearing an oath of loyalty to the British Crown. One particularly defiant captive, Fritz Duquesne, an Anglophobe to the end, joined the ranks of the few so-called “Irreconcilables,” who refused to take the oath. Instead, Duquesne snuck out of the reach of British officialdom in the company of another Boer resister. In hiding, he sought the aid of some of the Rock’s Boer sympathisers, prominent white Bermudians who had been aiding the prisoners throughout their captivity with supplies of food, clothing, carving tools to make their famous wooden souvenirs and other comforts. The young, curly-haired Duquesne, as charismatic and handsome as he was malignant, implored the genteel and wilful Anna Maria Outerbridge of Bailey’s Bay to aid his escape from the island. She needed little persuasion: naively, Miss Outerbridge even persuaded Duquesne’s fellow Boer escapee to turn himself in, in order to give the devilish Fritz a better chance at evading capture.


Devious Boer War prisoner and stowaway, Fritz Duquesne


St George’s shipping line owner Captain Meyer, another Boer sympathiser, was also in on the plot. After hiding out in a Hamilton brothel (did they tell Miss Outerbridge that?), Duquesne was able to stow away on one of Meyer’s vessels, landing free and insolent in an American port, en route to a long life of more skullduggery. It might have been better for the world if Duquesne had been caught, to rot in irons on the Rock: he went on to be an arch-spy and saboteur for the Germans in both world wars. For example, Bermuda historian Colin Benbow records that Duquesne’s espionage has been blamed by some for the disastrous loss of British military commander Lord Kitchener in the 1916 sinking of HMS Hampshire off the Orkneys.

But good men stow away, too. Such a feat dating from more recent times has once again been in the news, in a very different way than Carroll Wainwright’s or Fritz Duquesne’s cases. Historically, racism in Bermuda society, rooted in slavery until 1834, has meant unequal employment opportunities for blacks, just as it has to an even greater degree in the Caribbean. In the post-Second World War world, blacks in the Caribbean needed work, whereas post-war Britain, trying to rebuild after the war, needed workers. In June 1948, a dilapidated former German troopship, the Empire Windrush, set sail from Jamaica for England with 500 Jamaican workers and other West Indians aboard—including two soon-to-be famous Trinidadian calypso musicians.

What is less well-known is that when the aging ship had to repeatedly divert due to engine trouble, one of her unexpected ports of call for repairs was Grassy Bay, Bermuda. As a result, some black Bermudians, spearheaded by politician and labour leader Dr. E. F. Gordon, offered hospitality to the passengers, many of whom were military veterans who sought to be guest workers in Britain. And, while Bermuda was better than Jamaica as a home for young black males, it was decidedly no economic or social paradise for its black citizens. A few adventurous young Bermudian men accordingly snuck aboard the ship to try their luck on the other side of the Atlantic. Several were caught boarding and hustled back down the gangplank. Even so, some seven successful Bermudian stowaways were aboard when the ship docked in Tilbury, at the mouth of the Thames. One intrepid Bermudian stowaway jumped off the ship as it entered the harbour and swam to shore undetected in the frigid northern waters. A few of the handful of Bermudian stowaways made their lives in England, one becoming a prominent Brixton citizen, entertainer and social activist. In 2018, six decades later, the plight of the surviving passengers of Empire Windrush has again made front page news in the British papers. The black guest workers from this era, stowaways included, are currently fighting to have their full rights of UK citizenship for themselves and their descendants recognised. Why? Shockingly, despite the British government’s active recruiting of black guest workers in the era of the Empire Windrush’s sailing, no records of arrival were preserved by the British authorities in many instances—not even of the listed passengers, much less stowaways.

The illicit glamour of the stowaway story painted by writers like Robert Louis Stevenson thus fades fast when one looks into the Bermuda record. A recent review article in the New York Times Book Review by Michael Paterniti points out that choosing to become a stowaway, far from being a romantic quest, is often a desperate bid for transformation, with “something aspirational in such desperation.” I suspect that Carroll Wainwright Jr., looking back on his bewildered but determined boyish self on the Hamilton pier on that November day in 1934, might have agreed. So might many a Bermuda slave stowaway of yore.