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Caribbean Cold War: Anguilla vs the Empire

By Gary Oswald

Flag of the short-lived Republic of Anguilla

As discussed in the previous article of this series, the failure of the West Indies Federation of all of the UK's Caribbean territories to hold together long enough to gain independence as a single country was a huge headache for London. They were worried both that the UK would end up with continuing control over small islands which they wanted rid of and that once imperial power had withdrawn, local populations would turn to nationalist demagogues or communists. This distrust was aimed primarily at the small islands despite the fact that it was actually the leaders of the Big Islands, Jamaica and Trinidad, who had collapsed the federation.

The viewpoint was at least partly based on real issues, nationalism was a real factor as this article demonstrates. It was also, inevitably, partly driven by racism, there were paternal cultural assumptions that the Afro-Caribbeans were vulnerable to a combination of local extremism and insidious foreign influences. But, perhaps more than either it was driven by a political agenda. Even after the failure of both the West Indies Federation and the attempts to form a federation of the Eastern Antilles led by Barbados (which Barbados had withdrawn from on the basis that they didn't wish to be shackled to desperately poor and neglected ex colonies like Anguilla), London was against fragmentation and for the centralization of political authority. Painting the smaller islands as vulnerable to the evils of nationalism gave an excuse for that fragmentation to be avoided.

Kenneth Blackburne, who was Governor of the Leeward Islands for seven years and of Jamaica for five, came up with Whitehall's policy to counteract the influence of the "half baked rabble rousers’’ in the Leewards and Windwards Islands. He suggested that responsible West Indian leaders from the larger islands would be better placed than British administrators to counter the influence of the potential incendiarists in the smaller islands. Essentially Islands would become independent not on their own, but in groups. In terms of this article, the important polity is the Saint Christopher-Nevis-Anguilla associated state, a relatively artificial grouping of three islands.

Robert Bradshaw, the Chief Minister of St Kitts, was one of those potential ‘‘rabble rousers’’, he had come of age during the 1930s and 40s in which the British Carribean was wrecked with strikes of sugar workers as the sugar market collapsed. Bradshaw soon joined the St. Kitts and Nevis Trades and Labour Union and became President in 1944, the exact sort of man Blackburne so distrusted. However, Bradshaw redeemed himself in the eyes of London by fully supporting West Indies unification and being one of the major voices in favour of the Federation. So when that collapsed, he was deemed a responsible West Indian leader and St. Kitts was given leadership of the Saint Christopher-Nevis-Anguilla grouping, which was made an autonomous associated state as a first step towards independence.

This association was bitterly resented by the islands of Nevis and Anguilla. Both islands were desperately poor and had been horribly mismanaged by the British, Anguilla, with its poor soil, had spent much of the 1940s on the brink of famine. They had no phone network, no electrical grid, little water, only ramshackle housing and a severe lack of roads, schools and healthcare. And they were worried about that state continuing, as long as they could be outvoted by the more populous main Island. Would Bradshaw, an unashamed man of St. Kitts and dependent on voters there, invest government money into the other islands?

Anguilla and Nevis demanded some sort of local council or federated structure to ensure they could fund themselves, but Bradshaw wished to maintain centralised control. So he kept the ability to appoint and dismiss the local officials on Anguilla and Nevis, rather than have them elected. This was particularly resented in Anguilla as it was smaller and so more outnumbered, the result was that Anguilla's only elected official was one MP, Peter Adams, in a parliament where St. Kitts elected 7 and so Adams was easily overruled. This led to considerable ill feeling and worries of neglect. The early signs were also not promising, Bradshaw began his time in power by nationalising the sugar factories on St. Kitts and building infrastructure there, with revenue, investment and services being focused on the largest of the three islands. Adams also accused Bradshaw of using financial assistance from Canada which was ring fenced to build a pier on Anguilla to instead build that pier on St. Kitts. As discontent grew, the spark that lit the fire was, of all things, a beauty contest.

Robert Llewellyn Bradshaw, Premier of Saint Christopher-Nevis-Anguilla

In order to celebrate the new constitutional status of the islands, it was decided to hold a Miss Statehood competition, in which one woman would be chosen to represent all three Islands. Anguillan nationalists organised a partially successful boycott of this event, on the basis that their women should be competing for Miss Anguilla not Miss Saint Christopher-Nevis-Anguilla. On 4 February 1967, the Anguillan qualifying contest was held at the Valley Secondary School and crowds gathered at the event to throw rocks at the Kittian officials hosting it and chant anti unification slogans. The police present responded by firing tear gas at the crowd and called in for more reinforcements from St Kitts.

Because the police force was overwhelming Kittian and not Anguillan, it was viewed primarily as an occupying force. Policing with consent was impossible and so the Police station found itself repeatedly attacked by mobs and evacuated the Island entirely on the 30th of May over worries about the officers' safety. On the 11th of July Anguilla, then governed by a 'Peace Keeping Committee' of local notables, held a referendum on independence. 1,813 voters voted yes, compared to only 5 voting no and on the 12th of July, Peter Adams, MP and new Chairman of the Anguilla Island Council, declared Anguilla independent.

Saint Christopher-Nevis-Anguilla was at this point not yet independent itself, it was still an associated state of the UK and so Bradshaw sent repeated messages to Harold Wilson, the UK Prime Minister, asking him to restore order. If Anguilla could kick out the Kittians then would Nevis be next and if Nevis left, would Barbuda leave Antigua, would the Grenadines leave St. Vincent, would Carriacou leave Grenada, would Tobago leave Trinidad? If this domino was allowed to fall, the entire British strategy in the West Indies could collapse leaving them with dozens of small independent countries likely to call in dodgy foreign investors.

That foreign investment was the big fear that Whitehall had about Anguilla. A desperately poor island like that, which had unilaterally declared independence would need investment and London worried that the obvious options were either the Cuban Dictator, Fidel Castro or the American Criminal, Meyer Lansky, who had owned so many casinos in Batista's Cuba.

Bradshaw had more personal reasons to hate the separatists, on the 10th of June, prior to the referendum, an Anguillan rowing boat had landed on St. Kitts and armed men had attempted to storm Bradshaw's dwelling and take the man himself hostage. This came to nothing, probably fortunately for the Anguillans who would have lost a great deal of international sympathy had they killed or even kidnapped a state leader, but it was not forgotten.

And the Anguillans were actively courting that sympathy, opening their island for visits from British, American and West Indian reporters who would go home and write up sympathetic reports for the separatists, emphasising the economic neglect under British rule and the distance between St. Kitts and Anguilla. As many articles pointed out, there were actually four other islands in between the two, all owned by the Dutch, so how could they be a natural union?

In August 1967, the Anguillans even paid for a full-page advert for their cause in the New York Times. If Lyndon B. Johnson could be convinced to support Anguilla, then Wilson would be powerless.

Adams himself was also not that radical, he wanted independence, but he was happy to accept autonomy instead. As far as he was concerned union with the other two Islands was fine as long as London could guarantee him a functioning local council with certain autonomy to run affairs in Anguilla. But he could not sell that offer to his more nationalist allies and Bradshaw was not willing to compromise further with the people who had attacked his house with guns two months earlier.

The stalemate continued for eighteen months, with the British desperately trying to bring Adams and Bradshaw around the table and talks repeatedly breaking down as neither side was willing to accept the other's red lines. In December 1967, Britain had appointed a temporary administrator in Anguilla, Anthony Lee, as a compromise solution as the Kittians would not accept an Anguillan government and the Anguillans would not accept a Kittian. Lee would be there for 12 months and would be given the task to kickstart some economic development while Bradshaw and Adams agreed a long-term deal.

Lee had a decent relationship with Adams, but was hugely resented by the more radical separatists, increasingly represented by Ronald Webster, who had helped torpedo a deal in July of 1967 that Adams had been willing to accept. Webster and Lee hated each other, with the former resenting this continuing colonial control. In January 1969, after Lee's 12 months had passed, Webster redeclared independence and announced a constitution for the new Republic, with himself as President, Adams having been discredited by being willing to accept union. In February this was put up to another referendum and passed by 1,739 votes for to 4 votes against.

Ronald Webster

Lee, thoroughly rejected by the Anguillans, reported back to London that the new Anguillan constitution was ‘an instrument for establishing one man dictatorship' and that Webster was a pawn of shady American Businessmen. So advised, the British government resolved itself to remove Webster and his American allies, primarily an investor named Frank Holcomb about whom little was known but who Lee thought was linked to Meyer Lansky's Mafia. William Whitlock, MP for Nottingham North, arrived in St. Kitts in March 1969, where he managed to win the support of Bradshaw for Britain separating Anguilla from St. Kitts, as long as Webster, who Bradshaw blamed for the attack on him, would be removed from power. On the 11th of March, Whitlock arrived in Anguilla, where he was greeted with a rousing rendition of 'God Save the Queen'. Webster then invited Whitlock to meet him privately for lunch, Whitlock refused and was soon confronted by an armed mob of Webster's supporters who accused him of selling them out to St. Kitts. Whitlock at this point chose to leave the Island rather than carry out his planned negotiation on the basis that he felt unsafe. Being essentially expelled from the country at gunpoint was a humiliation and all but ended Whitlock's political career and Wilson, terrified that his government was losing face, ordered troops to move in to restore British control.

2 Royal Navy frigates, 300 troops of the Parachute Regiment and 22 officers from the Metropolitan Police Service arrived in Anguilla on the 19th of March 1969, prepared to restore British rule to Anguilla, with force if necessary. It wasn't necessary, they encountered no resistance at all, not a single shot was fired by either side during either the invasion or during the six weeks the troops remained posted there. In fact the Anguillans generally welcomed them with open arms, having always had a much bigger problem with Basseterre than London and charmed the Army as a result. Webster himself flew to New York where he argued the Anguillan case, as a victim of invasion, to the foreign press.

Their lack of armed resistance meant that in the other battle, the PR Battle, the Anguillans had been entirely triumphant. Britain came across as not only a bully, but a stupid one, attacking a completely peaceful people. George Brown, the Labour MP, unfavourably compared Wilson's action here with his inaction against the Rhodesian UDI in a question to parliament: "Are we to say that we can do it where there is only a rusty gun, but we cannot do it elsewhere, and our principles are decided by our estimate of the strength required?"

Wilson's cabinet, forced to justify an increasingly ludicrous seeming act, complained that they had been lied to by Lee and Whitlock as the troops had found no evidence of the unruly mobs, the communist radicals or the mafia dens they had been warned about. Frank Holcomb, the much-feared American investor, turned out to have no criminal connections at all, he just wanted to get government contracts for building infrastructure.

By the end of March, the British Government were eager to make a deal with Webster, viewing him increasingly as the victim of a campaign of slander organised by Lee and Bradshaw. Bradshaw was faced with the rotten pill of not only Britain separating Anguilla from St. Kitts but his arch enemy remaining in power. He wrote a series of angry letters to London complaining about this betrayal saying, 'this is unworthy of you and shames your government and I’m terribly surprised and sad that you expected me to accept it."

The UK had burned a lot of their reputation by invading Anguilla, but they hadn't actually solved the problem. They were still unable to find a solution which both Anguilla and Bradshaw would accept, and talks collapsed again in mid-May 1969. It wasn't until 1971 that an agreement was reached, which was essentially a repeat of the Lee deal of a temporary British administration, and not until 1980 that Anguilla was formally separated from St. Kitts and Nevis, two years after Bradshaw had died in office and more conciliatory leaders had taken over on both sides. St. Kitts and Nevis finally became fully independent in 1983, and Anguilla, deemed too small to be an independent state, became a British Overseas Territory and remains such to this day. This result, and Anguillan acceptance of it, has often led the events of the 1960s to be characterised as Anguilla revolting against independence, but that isn't really true. Anguilla wanted independence, they voted overwhelmingly for it twice, they just viewed being a British Overseas Territory as a more independent state than being part of St. Kitts and Nevis.

But what if Wilson hadn't forced that compromise on them, but had simply recognised Ronald Webster's Republic as legitimate? What would the Republic of Anguilla look like? It is an island of around 91 square km with a population of less than 16 thousand in 2022 and was at the time desperately poor with no real infrastructure and would be threatened by Kittian revanchism. It almost certainly would have had to accept an essential vassal status from the USA, possibly allowing a naval base to be built there, or American companies to survive but being reliant on foreign investment and treaties to survive is something that is true of a lot of countries. There are five currently independent countries smaller than Anguilla and three with a smaller population. It would be a microstate but so is the Pacific Island of Nauru which has kept itself going by variously strip mining for phosphate, becoming a tax haven and illegal money laundering centre, selling fishing rights, getting paid to detain refugees for Australia, foreign aid from richer countries and some small amount of tourism. Some of those routes would also be open for Anguilla, it already acts as a tax haven and fishing centre in our timeline after all.

An independent Anguilla might be an interesting setting for a story, in terms of filling the crime novel staple of a Caribbean island with no extradition treaties but ultimately it would have a limited effect on the outside world due to its small size. At the most it might, as a Republic in the British Caribbean, encourage those tendencies in its neighbours or change how London dealt with the other associated states in the area.

But for the around 5,000 residents of Anguilla in 1967 the independence or not of their country was something of enough importance that, very briefly, they were willing to fight the entire British Empire to gain it.


Gary Oswald is the editor of the 'Grapeshot and Guillotines' and 'Emerald Isles' Anthologies.


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