WI: Despite US independence, Long Island remains in UK hands

Even though Long Island followed the fate of the rest of New York when the US won its independence, the island was a loyalist stronghold during the war; what if the British had been able to hold on to it? Some of the people that emigrated to Canada after the ARW could head for Long Island instead, depending on how many people do so several scenarios are possible:

  • Long Island joins Canada
  • Long Island becomes a separate subject realm of the Crown
  • Long Island and the Atlantic provinces of OTL Canada form their own federation
 
I think LI is so far from the rest of Canada that it will remain a separate administration to the present day, assuming it survives. Which is not that crazy, provided that the British reinforce it with serious military force in the early decades to demonstrate they mean business about keeping it--otherwise it is too irritating and tempting and proximate for the USA not to take it at some point. But let a few generations pass with it remaining the case that Britain retains it and the USA will simply accept it is British territory for some "natural" reason. It is in the short term we have to figure on the knock-ons of such an intensely irritating provocation as this, British warships docking in plain sight of the US mainland, Loyalists the people of their various home towns want to hang again strolling about in plain sight to anyone on Manhattan (or is Manhattan included, and if not, why not?--and vice versa of course, Loyalists driven from their homes gazing back across the water to whatever the Yankees attempt to make up for lost New York City...the reasons the British could have militarily and logistically (at some cost) have done this but did not attempt it seem bloody obvious. So granting some fool of a negotiator insists on it and the Americans accept, then they have to pay the dues of these costs. Britain can do it; the question is, how unstable is it politically and thus militarily. The UK does not have to fortify the whole island (or islands, again I think it is logical to include all the islands leaving the USA New York state with just the parts that are firmly mainland) since something akin to mutual assured destruction protects the New York Island protectorate, but they do have to continually demonstrate that the force to inflict heavy retribution against any Yankee attempt to seize the protectorate is ready to hand, committed to the mission, and have some fortifications to slow down any foolish Yankee invasion attempt and buy time for the reasonable safety of the inhabitants, and guarantee some footholds which the British can reach by sea securely to land their counterforce.

As I say, let this situation stand some 50 years or so, and eventually the Yankees will simply accept "this is British territory" and leave it alone, reflecting also that conquest would be just awkward and as US-British relations improve, increasingly pointless. The tricky bit is getting past that first half century or so. On one hand, it seems a dagger aimed straight at the USA's heart, on the other...it kind of is! So in particular, there is both more irritation for a crisis like 1812, and more deterrent. Whether the upshot is to prevent a second round war between USA and UK, or to postpone it (time is on the side of the survivability of the USA in an all out war with Britain, and I think the longer the protectorate exists, the more certain it will be Britain will in fact be greatly outraged by a US conquest attempt and will follow through with all available force--note people argue about whether Britain could bring the USA to its knees as late as the 1860s or even later--so Yankees who would be deterred in the 1810s might dare try something aggressive in the 1830s) is a boat race between rising US capability and falling motivation. The mere existence of the New York Islands Protectorate is of course an extended provocation which will take time for USAians to get used to.

You seem more interested in stuff like "what is this place like in modern times?" Handwaving the whole question of necessary changes in US/British relations, which I think in the long run fade out and converge with OTL patterns by the 20th century, if we can get there without something massive changed, as I said I think the NYIP remains its own thing, much as Bermuda or the Bahamas do; there will be some ties to Canada, mainly in British Empire military planning and organization, Halifax being the next port in a chain of them back to Blighty, but no particular reason I see for the Protectorate or Dominion or whatever it is called to be annexed to Canada. As US/British relations eventually improve, I suppose by late Victorian times if not earlier, the island(s) are a valuable point of contact between US and British economic systems. Even if the USA keeps Manhattan, which I think is kind of silly, though perhaps a look at the map will cause me to rethink it, the British presence right over the water there will inhibit the development of NYC as we know it; perforce the US must develop some other major port city to become the premier city, or perhaps we don't develop one at all due to a sort of tendency to scatter to avoid creating a single target for British force deploying out of the Island(s) to strike at--not saying that will be a conscious policy, but that people will instinctively get nervous and so scatter their efforts. Dangerous knock ons for the Civil War crisis era here; the South might be better able to sustain itself industrially, and God knows if the British wanted to aid the CSA they'd have a tremendous advantage over OTL in doing that--albeit the stakes are high, if the USA can prevail you can bet this is the end of the protectorate as we insist on annexing it--or at least occupying it militarily and insisting on a long term neutralization with US inspectors preventing any British military buildup ever again. But I dislike stories about US/British conflict in the 1860s particularly those associating the British Empire with propping up CSA slavery, so let's just assume that particular confrontation never happens.

So, even if the USA can hold say Manhattan, I do believe the power and growth of NYC would not happen, despite the advantages of the port on the Hudson. Nor will the Island(s) grow to take the US metropolis's OTL place, since the USA will be leery of granting such a powerful role to a British protectorate. The region will be rusticated versus OTL--I imagine actually that as US-British relations relax, the economic potential will belatedly kick in on both sides of the international border, but the massive development of OTL will have a start delayed by decades, happening in inhibited slow motion early on, so that while eventually the confluence region will indeed be quite important, the role of the mighty conurbation of OTL will be either shifted elsewhere to one other US coastal location, or broken up. The upshot might be that by the middle 20th century, greater New York City area, including both US and British metropoli, will indeed be the USA's chief city anyway, but far smaller than OTL nonetheless.

Certainly once we get past US/British hostility, which in a sense in some sectors will be immediate, the very fact that the confluence region is a point of contact of the two systems will be a point in its favor. And it might for instance wind up the UN headquarters precisely for this very reason.

Other knock ons...Assuming we can antibutterfly to the extent that the overall pattern of OTL Great War remains much the same, with the USA sitting it out in the early years but eventually coming in on the Allied side, German U-boat activity much closer to US coastal waters would be more likely (assuming the U-boats have the range) since interdicting trade between the Island zone and Canadian maritimes would be plainly a "legitimate" war aim of the Germans. We see here how difficult it would be to unbutterfly actually; on one hand Yankees might resent the gun to our head preventing us from even considering favoring the Central Powers, and on the other provocations due to the Germans seeing it as their plain right to operate right off US shores would very likely draw us into the war much earlier despite the appearance of being frogmarched into it by the implicit British threat. (And if there are such perceptions, it could get very ugly because by the early 20th century at any rate, I don't think Britain would prevail in a knock out no holds barred US/British conflict--not in the immediate zone of North America anyway; they might prevail globally, but Canada and the protectorate would be toast and the resulting consolidated USA owning all of North America north of Mexico, and probably seizing all British footholds in the Atlantic and Caribbean too, would be vulnerable to damage but in no danger of being conquered or defeated in the region. Denied global reach perhaps, but such a conflict would be so costly to the British system I daresay they go under. So we have to assume that by 1900 at any rate, US/British conflict is practically unthinkable).

So--with minimal divergence from OTL, which gives us quite a job explaining how we get past the crises of 1812, USCW, and WWI, at the end of the day we have a reduced density of the Greater NYC area of OTL, with a political line cutting whatever islands are in the protectorate off but economically the two bailiwicks are one fused great urban industrial area, but lesser than OTL with other US cities taking up the slack somehow. Rather than annex the Island to Canada, considering the position of the protectorate on the major arterial communication route from US to Britain, I suppose it is more likely to politically join LI to Britain itself, with the region having its own seats in the Westminster Parliament, as a legally integral part of the UK! This can't practically happen until the 20th century I suppose, when telecommunications have advanced to the point that the colony can communicate in real time effectively. But prior to that, I don't think the situation there favors joining the Canadian federation, the concerns are all different. Heavy influence of the necessary heavy concentration of British military power there to deter Yankee adventurism will I think bind LI pretty tightly to Britain politically and culturally, and it might indeed be more practical than we might think at first to include LI as an overseas integral part of the UK more closely than most colonies.

Elsewhere I have argued strongly against the idea that if the Patriots lost the ARW and the British colonies were all retained, the post-rebellion settlement would be a happy belated adoption of the sorts of solutions that some think could have prevented the Revolution in the first place; rather Britain would double down in an authoritarian approach involving invidious creation of a noble class from the Loyalists and tight control of imperial authorities, with the majority of colonists not distinguished in their demonstrated loyalty denied rights and generally dominated. But this situation is entirely different; the migration of Loyalists from all over the USA would heavily populate the island with people of undoubted loyalty to the crown, and granting just the Long Islanders the sorts of extraterritorial integral British status the British colonial system denied Americans at large would make much more sense. So perhaps actually making LI a center of many county and borough MP seats would work even in the age of sail. Naturally the Anglo-Americans would be at a disadvantage in Westminster, but they'd not mind that too much considering how much protection they would want; they'll vote for strong imperial powers in their own vital self-interest. It would remain a special case, not a model for the British colonies in general, though actually it might work out for the Maritimes to come under a similar regime too. De facto autonomy and local government would simply be a practical necessity of course, but this need not stand in the way of being legally part of the core realms of the UK.

Honestly, I think the British trying for this would be a mistake, and it is hard to see how the arrangement survives the various crisis periods we can anticipate. Also I think that the diversion of development away from the confluence of US and British power centers, to strengthen Boston and the Chesapeake ports at the expense of central New York City, must have such important knock ons as to much transform the entire 19th century, including the conduct of a Civil War that seems inevitable; the North/South divide seems much accentuated and perhaps the secession of the South is more viable if the Chesapeake and Charleston are more developed. US/British conflict seems more provoked and either this means ultimate disaster for the USA, or perhaps instead for British North America across the board, but either way the anomaly of LI floating as a little bit of British power surrounded by Yankee holdings seems problematic, one side or the other seems likely to roll over that border.
 
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