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In 1967, the tiny Caribbean island of Anguilla launched one of the strangest revolutions in modern history. Its people were not fighting to escape the British Empire, but to remain a part of it rather than be governed from the neighboring island of St. Kitts. What followed included the expulsion of foreign police, a short lived republic, an invasion by British troops, and a constitutional battle that lasted for several years. Learn more about the odd story of the 1967 Anguilla Revolution on this episode of Everything Everywhere Daily. This episode is sponsored by Mint Mobile. Most of you might have something that you're saving up for. Maybe it's the trip of a lifetime, your children, your retirement, or maybe even something nice for yourself. And if you're looking for some extra money, the easiest thing you can do is to cancel your current mobile plan and switch to Mint Mobile. 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Years ago I visited the island and and it's where I first heard about the anguillan Revolution. Before 1967, Anguilla was one of the poorer and most neglected islands in the British Caribbean. It was first inhabited by indigenous people from South America long before European contact, with archaeological evidence on the island dating back many centuries. When Europeans discovered the island is uncertain. But English settlement began around the year 1650, mostly by settlers from the nearby island of St. Kitts. Unlike islands such as Barbados, Antigua or St. Kitts, Anguilla was dry, rocky and poorly suited to large scale sugar plantations, and that shaped its history. It never became a major plantation colony and instead developed as a small, isolated society of farmers, fishers, sailors and small landholders. Because Anguilla was poor and strategically unimportant, Britain didn't give it much attention. In the 19th century, it was increasingly administratively tied to the island of St. Kitts, the closest British controlled island. In 1871, Anguilla was attached to St. Kitts within the British Leeward island system. And in 1882St. Kitts and Nevis were merged into a single unit, with Anguilla effectively governed as a dependency. The problem was not just pride or local identity. It it was practical. Anguilla had few roads, limited public services, poor communications and little investment. Many Anguillans had to leave the island for work, especially as sailors, laborers and migrants. Elsewhere in the Caribbean, meanwhile, political power remained concentrated in St. Kitts, whose economy, population and political leadership dominated the combined colony. A protest from that era asked whether laws meant for Anguilla could ever be enacted with any regard for its interests when they were passed by men living on a distant island with no connection to Anguilla whatsoever. Over the course of more than a century, Anguilla saw almost no investment in roads, electricity, running water, healthcare or education. The island was in every practical sense neglected. A 1958 petition sought the dissolution of Anguilla's political and administrative association with St. Kitts. It protested about the dead hand of St. Kitts and warned that a people cannot live without hope for long without erupting socially. The petition went unanswered. The Crisis came to a head in the mid-1960s after the failure of the broader west indies Federation in 1962, a topic I covered in a previous episode, Britain decided it needed a new arrangement for its remaining small Caribbean territories. Under the proposed arrangement, each state, including the new combined St. Kitts, Nevis, Anguilla, would be fully responsible for internal self government, while Britain would retain responsibility for only external affairs and defense. The Anguillan people decided that they did not want to become part of a unitary state with St. Kitts and Nevis. They had protested enough about the lack of educational and health facilities, electricity, paved roads, running water and economic activity for their people and felt that after statehood they would now have no one left to protest to. Simply put, they feared that once Britain handed over internal governance, St. Kitts would have free rein to continue ignoring Anguilla, except that now they wouldn't be able to even appeal to the British. In 1966, a new constitution for the creation of the associated state was discussed in London. One of the proposals was the establishment of local government in Anguilla. The St. Kitts delegation agreed that the 1967 Constitution should contain a provision for Anguilla to enjoy a degree of local government. The fear in Anguilla was that the St. Kitts government had never intended to permit Anguillans any real degree of internal self governance. Key figures in Anguilla emerged to lead the resistance. Ronald Webster Atland Harrigan and Peter Adams organized public opposition in the months leading up to February 1967. British government experts were expelled, political rallies were sabotaged and there was a violent disruption at the State Queen show, an event organized by the government of St. Kitts to celebrate the creation of the new state. Despite the Anguillan objections, Britain went ahead regardless. On February 26, 1967, the Colony of St. Kitts, Nevis and Anguilla became an associated state. With the constitution taking effect the following day, Anguilla rejected the arrangement almost immediately. Protests, public meetings, anti statehood demonstrations and confrontations soon followed. The local government house was burned in March and the island's warden fled to St. Kitts. On May 29, at a meeting on the island, the crowd voted by a show of hands to expel the St. Kitts policemen from the island. The crowd left the park in procession and marched to the police headquarters, where they ordered the police to leave Anguilla by 10am the following day. After the demands were made, 17 policemen from St. Kitts spent the next 24 hours searching for ships, planes or anything that could take them on the 70 mile journey back home. On May 30, the police were disarmed and flown out. The expulsion of the St. Kitts police marked the start of Anguilla's effective separation from the new associated state. Everything was bloodless, but it was a significant event in the island's history. In June 1967, Anguilla's leaders sent a delegation to St. Kitts seeking a peaceful settlement. And their position was not vague. They said Anguillans did not want to be part of St Kitt's Nevis Anguilla and wanted separation and self determination, ideally as a state associated with Britain. St. Kitts responded by declaring a state of emergency and appealing for regional help to suppress the rebellion. Fearing an invasion from St. Kitts in retaliation, the revolutionary leaders decided on an unusual preemptive move. Anguillems took the initiative and devised a rather ham fisted attack on the island of St. Kitts on the morning of June 10, 1967. They embarked upon what has to be one of the most naive failures in the history of military aggressions. And yet, oddly enough, the mission achieved its goals. The attack did almost nothing in the way of damage, but it demonstrated that Anguillans were serious and willing to act and it rattled the St Kitts government enough to pause any retaliatory plans. And here I should Note that in 1967 Anguilla had a population of just 6,000 people while St Kitts had a population of of about 36,000. After the expulsion of the St Kitts police, Anguilla effectively governed itself. Elections were held, an Anguilla council was formed and the island sought international attention. Angolan leaders appealed to the United nations for assistance, arguing that their situation was a colonial problem. Britain resisted UN involvement, arguing that Anguilla was part of an associated state and therefore not a matter for the UN's colonial committee. Britain attempted a compromise in January 1968 by sending Tony Lee, a senior British official, during an interim period. This was meant to calm the crisis while negotiations continued, but it did not solve the underlying issue. Anguillans were still adamant that they would accept nothing short of full separation from St Kitts. Britain, however, maintained that all under the West Indies act of 1967 it could not simply detach Anguilla from the associated state without the consent of St. Kitts. When the interim period ended in early 1969 and Britain refused to extend it, Anguilla's leaders moved towards unilateral independence. In February of 1969, Angola held a referendum and the result was overwhelming. 1,739 votes in favor of independence and only four were against. Ronald Webster was declared president of the new Republic of Anguilla. This republic was never internationally recognized, but it represented Anguilla's clearest declaration that it would not return to rule from St. Kitts. In March 1969, Britain sent William Whitlock, a Foreign Office minister, to Anguilla with a proposal for renewed British administration through a commissioner. Angolan leaders rejected the proposal and Whitlock was expelled from the island. This embarrassed the British government and convinced London that it needed to reassert control. On March 19, 1969, British paratroopers, Royal Engineers and London police officers landed on Anguilla in what was called Operation Sheepskin. The operation became famous partly because of its absurdity. Britain was invading a tiny island whose people largely wanted to remain linked to Britain. They just didn't want to do it through St Kitts. There was no real battle. The local defense force had already given up its weapons because resistance would have been futile and might have caused bloodshed. The rebellion ended without a shot being fired. The British troops ended the Republic of Anguilla, but perhaps more importantly, they did not restore control of Anguilla to St. Kitts. Militarily, Britain crushed the rebellion, but politically, Anguilla won the central argument. British leaflet supportedly reassured residents that Britain did not intend to force them back under a St. Kitts administration they did not want. Soon afterward, Britain installed a commissioner and began direct administration of Anguilla. After the invasion, Anguilla didn't quietly accept direct British rule either. There were demonstrations demanding the withdrawal of British forces, and Angolan leaders initially refused to cooperate. Britain sent Lord Caridon to negotiate, producing the Caridon Declaration, which promised that Anguilla's administration would be carried out in consultation with the island's elected representatives. Ronald Webster was recognized as the leader of the Anguilla Council. The next few years were a period of constitutional experimentation. Britain appointed the Wooding Commission to seek a durable solution, but its recommendations were rejected by the Anguillans because they still didn't provide the complete break from St Kitts that the island demanded. By 1971, Britain concluded that the dispute was irreconcilable and passed the Anguilla act, which allowed it to administer Anguilla directly. The arrangement was technically awkward because Anguilla still remained part of the associated state with St Kitts on paper, but in practice it was now separately administered. Formal separation finally came in 1980. By then, the leader of St Kitts, Robert Bradshaw, had died. And the political climate had changed. The anguilla act of 1980 empowered the Crown to separate Anguilla, and on December 19, 1980, Anguilla finally ceased to have anything whatsoever to do with St. Kitts. St. Kitts and Nevis became independent in 1983 and Anguilla did not join them. Instead, it remained under British control, eventually becoming a British overseas territory, which remains Anguilla's status today. For the most part, Anguilla has been content with its current status as a British overseas territory. They are largely autonomous, with democratically elected representatives who make decisions for all internal affairs on the island. The British, however, are responsible for foreign affairs and defense. The British have stated that they will neither force independence nor stand in the way. The general consensus on Anguilla is that independence is a long term aspiration but not an immediate priority. Most people think that they're not yet ready for independence and if they did become independent. With a population of under 16,000 people, they would be the third smallest country in the world, just ahead of Nauru and Tuvalu in the Pacific. May 30, the day the St. Kitts police were removed, is celebrated as Anguilla Day and the leader of the revolution, Ronald Webster, has been recognized as the father of the nation. The Anguillan revolution remains one of the oddest revolutions in history. Nobody was killed, although there were two minor injuries. Unlike other revolutions, this wasn't about breaking away from a colonial power. It was about remaining a British territory just because they didn't want to be ruled by a nearby island. The executive producer of Everything Everywhere Daily is Charles Daniel. The associate producers are Austin Otkin and Cameron Kiefer. My big thanks go to everyone who supports the show over on Patreon. Your support helps make this podcast possible and I also want to remind everyone about the community groups on Facebook and Discord. That's where everything happens that's outside the podcast, and links to those are available in the show Notes. As always, if you leave a review on any major podcast app or in the above community groups, you too can have it read on the show.
Host: Gary Arndt
Date: May 21, 2026
Episode Theme:
A detailed look at the unique and largely bloodless Anguilla Revolution of 1967, when residents of Anguilla rebelled—not to gain independence from Britain but to remain directly under British governance rather than succumb to rule from neighboring St. Kitts. The episode traces Anguilla’s colonial neglect, the dramatic events of the revolution, its aftermath, and the island’s modern status.
Gary Arndt explores the little-known 1967 Anguilla Revolution, a uniquely peaceful and paradoxical uprising where the people of Anguilla sought to remain under British rule rather than be managed by the government of St. Kitts. The episode walks through the historical backdrop, key events, and the quirky, sometimes absurd, nature of the "revolution"—culminating in Anguilla's status as a British Overseas Territory.
On colonial neglect:
On Anguillan motivation:
On British intervention:
On the revolution’s uniqueness:
Gary Arndt maintains an engaging, relatable, and lightly humorous style throughout:
This episode highlights the fascinating case of Anguilla—a tiny island where revolution meant seeking closer ties to their colonial ruler rather than independence, and where almost nobody was hurt in the process. The Anguilla Revolution stands as a case study in the unpredictability and nuance of colonial legacies, local identity, and self-determination.