WI: the British and French in 1920 sold Caribbean Colonies.

There were actually Congressional proposals in at least 1936 to annex European colonies in return for canceling WWI debts, but the U.S. Army was opposed to those proposals.
The question of acquiring new base facilities in the Western Hemisphere had been explored on various occasions before August 1939. In a thorough canvass of the problem in 1936, prompted by Congressional proposals to annex European possessions in return for cancellation of World War I debts, the Army came to the conclusion that no move of this sort would be wise. The Army assumed that it was against national policy to acquire new territory except for urgent strategic reasons. It also assumed that the Latin Americans would resent the territorial expansion of the United States within the Western Hemisphere, either in their own territory or in the possessions of the European powers. Any such move by the United States would be certain to raise anew the cry of "Yankee Imperialism" and undermine the friendly relations recently established through the "Good Neighbor" policy. The Army examined in turn every colonial area in North and South America and concluded that none of them had a military value sufficient to offset the disadvantages of American ownership. On the other hand in 1936, as well as later, the Army expressed its strong opposition to the transfer of any existing European possession to another Old World power.
 
What If the British and French sell their Caribbean colonies (and maybe the Falklands) to the United States in 1920 to help pay off their debt.
Britain would rather transfer (most of) its Caribbean colonies to Canada - if Ottawa was more cooperative and wasn't so hung up on racial matters - instead of selling them to the US. From there, whether or not they want to remain part of Canada or go independent would be up to the ex-colonies themselves.

Meanwhile, the South Atlantic colonies are probably still too valuable for the Royal Navy to let go, although in the case of the Falklands - if Britain wanted to dispose of it - the better option would be to wait and see for a cooperative government in Buenos Aires to negotiate. In this case, in 1920 the President of Argentina was Hipolito Yrigoyen, the "Father of the Poor", its most progressive one at that point in time; meanwhile, the Falklands was still in a feudalistic relationship with the Falkland Islands Company, which dominated not just the economy but also its society. For Yrigoyen to negotiate the peaceful handover of a British archipelago to Argentine sovereignty, at a point where British dominance was pervasive in all faces of Argentine life, would be quite a coup for the government.
 
Britain would rather transfer (most of) its Caribbean colonies to Canada - if Ottawa was more cooperative and wasn't so hung up on racial matters - instead of selling them to the US. From there, whether or not they want to remain part of Canada or go independent would be up to the ex-colonies themselves.

Meanwhile, the South Atlantic colonies are probably still too valuable for the Royal Navy to let go, although in the case of the Falklands - if Britain wanted to dispose of it - the better option would be to wait and see for a cooperative government in Buenos Aires to negotiate. In this case, in 1920 the President of Argentina was Hipolito Yrigoyen, the "Father of the Poor", its most progressive one at that point in time; meanwhile, the Falklands was still in a feudalistic relationship with the Falkland Islands Company, which dominated not just the economy but also its society. For Yrigoyen to negotiate the peaceful handover of a British archipelago to Argentine sovereignty, at a point where British dominance was pervasive in all faces of Argentine life, would be quite a coup for the government.
What does this have to do with my what if?
 
I think it might have been possible for the USA to take possession of some islands in the Caribbean or maybe the pacific we just need the worth of the islands to out way the costs of getting them. As others have pointed out, there were definitely viable proposals for the Europeans to sell the islands, but I think we would need to change to give the USA a strategic reason to buy the islands that would outway the cost in worsened relations with Latin America. Maybe there is a much more aggressive and pro german Venezuelan Dictatorship in the 30s that begins to concern the United States especially as it allows German ships to have a base in the Caribbean this leads to the US government buying the islands to once and for all secure the Caribbean for any future wars.
 
This would have been a win-win for everybody.

Britain and France offload a financial burden, not just the debt, but in economically and strategically unimportant and costly colonies that are a hangover from the 18th century. There is little need or benefit in holding on to most of these colonies.

The US gets to progress it's "Manifest Destiny", reducing European influence in the Americas, turning the Caribbean into a US lake and is able to project influence deeper into Latin America.
 
This would have been a win-win for everybody.

Britain and France offload a financial burden, not just the debt, but in economically and strategically unimportant and costly colonies that are a hangover from the 18th century. There is little need or benefit in holding on to most of these colonies.

The US gets to progress its "Manifest Destiny", reducing European influence in the Americas, turning the Caribbean into a US lake and is able to project influence deeper into Latin America.
It also adds strategic depth to the USA.
 
Its not ASB but this would require some extraordinary changes to American politics to achieve. The conquest of the Philippines was already controversial and by the 1920s it was understood by everyone involved that the best course of action was to establish a friendly regime on the island and pull out. American imperialism post Spanish American War had entirely moved on to soft power and limited interventions only when absolutely needed to prop up their puppet states, there was no longer any real desire to expand the US’s territory further.

Most of the British and French possessions in the Caribbean at that time were small, lowly populated, impoverished, and lacking in any natural resources. Many of them rely on Tourism nowadays to make money, something that didn’t take off until the jet age and completely unknown to decision makers of the 1920s. They didn’t offer the navy ports in an area it didn’t already have ports and would’ve cost far more to administer than they would’ve returned in tax revenue. The US had no interest in annexing such land because the real world isn’t a video game and making the name USA bigger on a map for no real reason isn’t something any serious politician wanted.

And everyone has seemingly sidestepped the race matter entirely. No treaty is getting through the senate without the votes of southern senators. And no southern senator is voting for a bill that lays the groundwork to admit a half dozen majority black states into the union. Fuck, many of the northern ones wouldn’t want that either.
 
Regarding the chance of a Caribbean state, I do not see that happening. There are too many people of color for admission as a state. They probably would be come a commonwealth like PR. ie half in and half out.
Hawaii had a majority nonwhite population, and it still got admitted. I think the English-speaking Caribbean would be admitted (at least the parts with sufficient population) during the civil rights era. The non-English speaking areas (and English speaking parts with smaller populations) might end up like Puerto Rico and the Virgin Islands though.
Countries generally don't 'sell' territory like that, unless at gunpoint or in extreme circumstances of imminent risk.
Russia sold Alaska when it was a financial drain, although that also eliminated the risk of losing it to the Brits. The Danes sold the Virgin Islands because they were a financial drain.
When they expanded from the original 13 states.
The US had colonial issues before then, seeing as those 13 states started out as British colonies.
Its not ASB but this would require some extraordinary changes to American politics to achieve. The conquest of the Philippines was already controversial and by the 1920s it was understood by everyone involved that the best course of action was to establish a friendly regime on the island and pull out. American imperialism post Spanish American War had entirely moved on to soft power and limited interventions only when absolutely needed to prop up their puppet states, there was no longer any real desire to expand the US’s territory further.
More colonialism in Asia would be difficult to achieve, and having the Philippines as a US colony would probably be considered ASB if it hadn't happened. Colonies and expansion in the Americas on the other hand could easily be tied to Manifest Destiny and in this case the Monroe Doctrine.
Most of the British and French possessions in the Caribbean at that time were small, lowly populated, impoverished, and lacking in any natural resources. Many of them rely on Tourism nowadays to make money, something that didn’t take off until the jet age and completely unknown to decision makers of the 1920s. They didn’t offer the navy ports in an area it didn’t already have ports and would’ve cost far more to administer than they would’ve returned in tax revenue. The US had no interest in annexing such land because the real world isn’t a video game and making the name USA bigger on a map for no real reason isn’t something any serious politician wanted.
American businesses, especially agribusinesses were already deeply involved in the Caribbean. Also real life may not be a video game but its not an accounting spreadsheet either. Economics matter but they're not the sole factor. If there was a serious offer in the 1920s, Washington would probably take it. The general public including the political elite would be mostly in favor because it would reduce European influence in the Americas, expand the country at time when Manifest Destiny was still within living memory, and generally appeal to national pride. Those factors will win out over bureaucratic projections of tax revenue from the Treasury department.
And everyone has seemingly sidestepped the race matter entirely. No treaty is getting through the senate without the votes of southern senators. And no southern senator is voting for a bill that lays the groundwork to admit a half dozen majority black states into the union. Fuck, many of the northern ones wouldn’t want that either.
In the 1920s they'd just be becoming US territories.
 
Random thought with all of those keys could the US use them to practice amphibious assault when WW2 comes around.
 
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The 1980 GOP presidential ticket (Ronald Reagan-Eugenia Charles):

reagan-charles.jpg
 
I don't see the U.S. ending up getting all of these islands, maybe except for the Bahamas or the Turks and Caicos since it is close to Florida and Puerto Rico. This would probably mean a faster expansion of the United States Navy inorder to cover all those areas.

I'm curious how it would look like if Belize and Guyana are U.S. protectorates/territories/insular areas.
 
I know that we are focus on the Caribbean but, I also wonder about the following:

Saint Pierre and Miquelon (/ˈmɪkəlɒn/),[3] officially the Territorial Collectivity of Saint-Pierre and Miquelon (French: Collectivité territoriale de Saint-Pierre et Miquelon [sɛ̃ pjɛʁ e miklɔ̃]), is a self-governing territorial overseas collectivity of France in the northwestern Atlantic Ocean near the Canadian province of Newfoundland and Labrador.[4][5] An archipelago of eight islands, Saint Pierre and Miquelon is a remaining vestige of the once-vast territory of New France.[4] Its residents are French citizens; the collectivity elects its own deputy to the National Assembly and participates in senatorial and presidential elections. It covers 242 km2 (93 sq mi) of land and had a population of 6,008 as of the March 2016 census.[note 1][1]

I wonder if they could be included in the deal?

In my personal opinion, I think that the USA would do it. When I was young, my older relatives felt that the Europeans conned us into coming into WW1 to save them and their empires. They then stiffed us on the debt. They often said the European countries should get out of our part of the world. Furthermore, they really felt that we should stay on our side of the Atlantic and the Europeans stay on theirs. So I can see the USA doing this to get something in exchange for our loans and to remove the European influence from "our area". I suspect that my older relatives would want to buy Greenland from the Denmark and the Dutch colonies. They were ordinary middle class educated people so, I am assuming that many other Americans of that time thought the same.

I am enjoying reading the comments on this idea and hope that people keep sharing their thoughts and opinions.
 
I know that we are focus on the Caribbean but, I also wonder about the following:

Saint Pierre and Miquelon (/ˈmɪkəlɒn/),[3] officially the Territorial Collectivity of Saint-Pierre and Miquelon (French: Collectivité territoriale de Saint-Pierre et Miquelon [sɛ̃ pjɛʁ e miklɔ̃]), is a self-governing territorial overseas collectivity of France in the northwestern Atlantic Ocean near the Canadian province of Newfoundland and Labrador.[4][5] An archipelago of eight islands, Saint Pierre and Miquelon is a remaining vestige of the once-vast territory of New France.[4] Its residents are French citizens; the collectivity elects its own deputy to the National Assembly and participates in senatorial and presidential elections. It covers 242 km2 (93 sq mi) of land and had a population of 6,008 as of the March 2016 census.[note 1][1]

I wonder if they could be included in the deal?

In my personal opinion, I think that the USA would do it. When I was young, my older relatives felt that the Europeans conned us into coming into WW1 to save them and their empires. They then stiffed us on the debt. They often said the European countries should get out of our part of the world. Furthermore, they really felt that we should stay on our side of the Atlantic and the Europeans stay on theirs. So I can see the USA doing this to get something in exchange for our loans and to remove the European influence from "our area". I suspect that my older relatives would want to buy Greenland from the Denmark and the Dutch colonies. They were ordinary middle class educated people so, I am assuming that many other Americans of that time thought the same.

I am enjoying reading the comments on this idea and hope that people keep sharing their thoughts and opinions.
I’m gonna say yes Miquelon, Saint Pierre and Bermuda are included. I’m guessing that the area is going to have an economy very similar to Hawaii, and that the United States Navy’s going to take interest in the outlying island. To help with elicitation here’s a detailed map of the area in question.
19C24E6C-8914-467C-9313-A7C6D0E35990.jpeg
 
In any case, think the British would at least keep Jamaica and maybe also the Caymans? And I feel like Miquelon and St. Pierre would be given to Canada in exchange for a small reduction in French denbts owed to the UK.
 
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In any case, think the British would at least keep Jamaica and maybe also the Caymans? And I feel like Miquelon and St. Pierre would be given to Canada in exchange for a small reduction in French denbts owed to the UK.
The basic perception of this thread is that the British empire sells these things to the United States for a reduction in debt. Let’s say 2/3. Why on earth with the United States cancel debt for sale to Canada?
 
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