THE INVASION OF ANGUILLA: A Comedy Of Errors, Caribbean Style

Mortal enemies: Robert Bradshaw, leader of St. Kitts (left), and Ronald Webster, provisional leader of Anguilla (right)

Charles Doane Charlie is Cruising editor for SAIL and has been associated with the magazine since the mid-1990s. He has more than 45,000 bluewater miles under his keel, including six transatlantics and three singlehanded passages, and has owned and maintained three different cruising boats over the years.

Charles Doane
Charlie is Cruising editor for SAILMagazine



I first learned of the British invasion of Anguilla, which took place in March 1969, while studying Don Street’s Transatlantic Crossing Guideseveral years ago. In his classic tome (which I can still recommend as a great general reference if you are cruising the islands of the North Atlantic), Don mentions the event in passing and cites two books treating it. One, The Mouse That Roared, he claims is a fictionalized account of the invasion; the other, Under An English Heaven, he cites as a factual account.

The Mouse That Roared, by Leonard Wibberley, which I read as a boy, in fact was published in 1955, 14 years before the invasion of Anguilla took place. It tells the tale of a fictional European micro-nation, the Duchy of Grand Fenwick, that declares war on the United States, hoping to garner a bonanza of foreign aid after its inevitable defeat. Instead, through a series of improbable events, Grand Fenwick ends up in control of a U.S. secret weapon, the Q-Bomb, and in effect conquers the world. Though the book has nothing to do with Anguilla, its comic spirit does mirror that of the real-life improbable events that led Britain to invade Anguilla after the tiny island rebelled against independence from the British crown.

Nope, that’s not a typo. They rebelled against independence.

I finally got around to reading the second of Don’s recommended books this past winter and it was, as advertised, directly on point. Appropriately, it was written by a prolific comic crime novelist, Donald E. Westlake, and though the narrative is certainly tongue-in-cheek and also very entertaining, it is scrupulously researched and near as I can tell is still the most detailed account of both the invasion and the long series of events leading up to it.

The problem in a nutshell was that the British, as far back as 1822, had always insisted on administering its possession of Anguilla through the colonial government it  established on St. Kitts, in spite of the fact that Anguilla would much rather have been ruled directly by Britain. And when Britain granted independence to its West Indian colonies in the 1960s, it again rather negligently lumped Anguilla in together with St. Kitts (and also Nevis). It didn’t help matters that the newly independent nation was ruled by one Robert Bradshaw, an ex-sugar worker and labor leader from St. Kitts, who openly despised Anguillans.

“I will not rest,” Bradshaw once declared of Anguilla, “until I have reduced that place to a desert.”

Though the Anguillans strived mightily to alert the British to the fact that they could not abide being ruled from St. Kitts, their pleas fell on deaf ears. A few months after the associated state of St. Kitts-Nevis-Anguilla became officially independent in February 1967, the Anguillans effectively seceded by chasing 17 police officers from St. Kitts off their island. The rebel flag they hoisted after committing this heinous act of insurrection was the British Union Jack.

Police station

Flag raised after the Anguillans liberated their police station


There followed many months of comic opera. Various outsiders tried to exploit Anguilla’s new ambiguous status for their own ends. Robert Bradshaw made noises about invading Anguilla. The Anguillans formed a provisional government and launched an abortive raid on St. Kitts, hoping to kidnap Bradshaw and hold him hostage until Great Britain recognized their secession from St. Kitts. Bradshaw meanwhile insisted that Anguilla had been taken over by the American Mafia.

The British finally sent an incompetent diplomat, William Whitlock, to Anguilla to try to sort things out. Whitlock was greeted by the island’s provisional leader, Ronald Webster, and a crowd of people who were waving pro-British posters and singing God Save the Queen. Whitlock in response totally dissed Webster and the Anguillans. After his people tossed out leaflets to the crowd detailing the British proposals for ending the crisis–“as a farmer might throw corn to fowl” was how the local newspaper described it–Whitlock refused to ride in the motorcade Webster had organized to receive him. He also refused to have lunch with Webster. Afterwards, the young toughs who had styled themselves as Anguilla’s Defense Force, over whom Webster had no effective control, intimidated Whitlock and his group by brandishing the few firearms they possessed, whereupon the so-called diplomat fled the island.

Bradshaw and Webster

Mortal enemies: Robert Bradshaw, leader of St. Kitts (left), and Ronald Webster, provisional leader of Anguilla (right)


William Whitlock

William Whitlock, the man who precipitated the invasion

Believing the Queen’s anointed representative had been fired upon and forcibly ejected from Anguilla, the British immediately laid plans to invade. The invasion, code-named Operation Sheepskin, was a badly kept secret, so the Anguillans had plenty of time to prepare. These preparations consisted of a complete demilitarization, in which all guns on the island were taken over to St. Martin and buried. The invasion force, consisting of two British frigates, 135 paratroopers, and 40 Scotland Yard police officers, was greeted by a horde of foreign journalists and met no resistance from the local populace.

Goat patrol

Elements of Britain’s Red Devil parachute battalion on goat patrol

Swimming cops

London police take a swim after helping to invade the island

The world’s press was derisive in its commentary. Time magazine described the invasion as “Britain’s Bay of Piglets.” The British Spectatortermed it “The War of Whitlock’s Ear.” Newsweek’s headline was “The Lion That Meowed” (which may explain how Don Street got confused about The Mouse That Roared). Mr. Whitlock lost his job and never again worked for the British government. But in the end–here comes the happy ending–Anguilla finally got what it wanted all along: direct rule from Great Britain.

It was, I believe, the only time in history that a country has launched an insurrection in order to become a proper colony.

This is only a capsule description of the whole sordid affair, with all sorts of juicy and hilarious details left out. To enjoy the full course of absurdity you really need to digest the book. It’s the perfect thing to read while lolling about on a boat in the Caribbean. The book is out of print, alas, but you can always find a copy at my favorite used-book

Under An English Heaven, by Donald E. Westlake
Simon and Schuster, 1972 (278 pp.)

This article was syndicated from Wavetrain

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