Saaremaa/Hiiumaa as Taiwan?

Is it feasible for these estonian isles to support separate (White) state from mainland (Red) Estonia?

No, too tiny. A better analogue would be a White Russian government surviving in Alaska. This would take place in a TL where Russia doesn't sell Alaska, but where WW I and the revolution still occur roughly the same way. It requires a bit of a butterfly net, but it's not impossible.
 
Is it feasible for these estonian isles to support separate (White) state from mainland (Red) Estonia?

I think they need to be further out from Estonia, something like in a chain with the Aland or Gortland islands ? (or you could have a Aland island itself in a Red Finland scenario)

Too near USSR and too far from any pro-USA nation. It wouldn't survive many weeks.

Not sure USA matters as its will happen in 39/40 well away from USA.

You do though need somebody to stand up for the islands, Sweden/Finland maybe ? (or Germany but that raises other problems with what happens post WW2)
 
You do though need somebody to stand up for the islands, Sweden/Finland maybe ? (or Germany but that raises other problems with what happens post WW2)

I see something like this happening if both Finland and Estonia were attacked by the Red Army simultaneously in late 1939 and Estonia, unlike IOTL, decided to fight. Finland holds the front as IOTL, but Estonian defence starts collapsing in weeks due to the conditions being more suited to the Red Army south of the Gulf of Finland. As the Estonian troops fall back towards Tallinn and the west, a contingent of the Estonian government flees Tallinn in a fleet of few navy and civilian ships supported by icebreakers.

The Estonians and Finns had defence cooperation against the Red threat in the 1930s and in the event they would at the very least coordinate their naval actions against the Soviets. It is possible Finnish Navy ships (in the main, the state icebreakers) would then help the fleeing convoy reach Saaremaa (and avoid any known minefields) and set up in Kuressaare which becomes the temporary Estonian capital when Tallinn inevitably falls.

The Finns send what help they can to the Estonians in the islands as the Red Army takes over rest of the nation's mainland, and ask others to join in. Due to the winter conditions, though, very few are able to do this, perhaps apart from the Swedish who could possibly send strictly civilian aid to the islands in an icebreaker-led convoy without endangering their neutrality.

I can't see this Estonia-in-the-islands lasting any longer than a few months, though. If the Winter War ends historically, Finland will be forced to pull back any limited support it could have offered to the Estonians and they would be left alone.

The Soviets would then have free hands to take the islands over, in an amphibious operation as soon as the ice clears a bit, or even already during the winter though it might be difficult. At the end of it, I see the USSR snuffing out the Estonian government's and military's last outposts here in, say, May-June 1940. It is likely that some of the Estonian officials would flee to Finland or Sweden and then continue further abroad to set up a government-in-exile in London, say, prior to the island's demise.

There would be a lot of small butterflies due to this all, and they would add up, but I can't immediately see any major effects to WWII being caused by the events. Further afield, the fact that Estonia actually fought (and was supported by the Finns in this), would be important for the Estonians in national terms and have an effect on their self-image.
 
Wasn't there a significant Swedish population on one of the Estonian islands, it might become a second Aland.

There was an Estonian-speaking majority in the islands, Swedish-speakers made up the majority in just a few select places. The number of Estonian Swedes did not total 10,000 or reach 1% of the national population in 1939, and even if the islands had more than average numbers of Swedish-speakers, the situation was not comparable to the essentially monolingually Swedish-speaking Åland. According to Estonian Wikipedia, for example, the biggest town on Saaremaa, Kuressaare, had in both 1922 and 1934 about 10 x the number of German- and 3-5 x Russian-speakers than Swedish-speakers.

I think that we can expect a lot of the Swedish-speakers to flee west in most scenarios where even the mainland of Estonia is taken over by the Soviets anyway.
 
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Here's a thought - in DrakonFin's scenario of a Finland+Estonia vs USSR winter war, Estonia "sells" the islands to Sweden. Could it work?
 
Here's a thought - in DrakonFin's scenario of a Finland+Estonia vs USSR winter war, Estonia "sells" the islands to Sweden. Could it work?

It seems pretty unlikely.

In theory, the Swedish could announce that they have just bought the islands from the legal Estonian government, move a naval squadron to Kuressaare and start ferrying troops to the islands. If they manage to look convincing in such an endeavour, and apparently committing a lot of resources and troops to it, even Stalin would think twice before actually attacking the newly Swedish islands as a full-scale war against Sweden might be in 1940 beyond his plans and might backfire expensively. In other words, purely in theory it might work.

However, I find it hard to believe any Swedish government we could realistically have in 1940 would find in itself the brinkmanship and pure cojones to pull off such a scheme, and convincingly enough with required bravado to boot. In essence, we are expecting Stockholm to blindside Stalin and make him reel in surprise, the Swedish government acting almost as ruthlessly and decisively than the Soviet leader himself. It is a pretty tall order.

Incidentally, I started thinking about writing a small vignette in line with my above scenario. If I get around to it, I'll post it here. So watch this space.:)
 
Suppose the Germans in 1944 do not defend Narva, but instead puts a larger defense on the islands instead, which makes them remaining in German control until May 1945, like Courland.

The problem then is to get another power than the Russians to take them, and there is none, but if all forces in Estonia 1944 have their equipment there, and not lose it during a defense of mainland Estonia, and all Estonian refugees move to these islands instead, and a lot more Estonians leave the mainland due to the proximity of the islands compared with Sweden, we might have a much larger population that is well armed and capable of defending itself.

In that case, say 200 000 Estonians form an independent state here in 1945, while the Soviet Union holds the rest of Estonia.
 
Couldn't RN protect the islands from the soviets.say Estonia is overrun by the Reds during the Russian civil war and the whites fled there .
 
Couldn't RN protect the islands from the soviets.say Estonia is overrun by the Reds during the Russian civil war and the whites fled there .
You'd need the RN to commit to permanently defending the islands, even in the face of WWII. The Soviet Navy was hardly the RN, but it was more than capable of crushing any Estonian defenses that could possibly be put in place locally.

Taiwan was able to survive because China had very little naval capability and the USN was backing it. The Soviets had significantly more (mostly inherited from the Tsar, but still more than capable of defeating the Estonian Navy). The UK in the aftermath of either World War was far too exhausted to start a war over some miscellaneous islands in Eastern Europe.

And even if they wanted to, they would eventually have to pull out as tensions rise with Germany; a naval deployment in the Baltic is a disaster waiting to happen should WWII break out. Don't forget OTL's WWII saw the UK refuse to declare war over the Soviet invasion of Poland, a nation they were officially fighting to protect, much less the annexation of the various Baltic states. Do you expect them to start a war with the Soviets over a few indefensible islands in the Baltic?
 
Finland itself is the Taiwan analog from 1919 to date.

Not an exact analogue but it is interesting to note that of all the nations now existing that were part of the Russian Empire prior to 1917, Finland has the most direct institutional and legal continuity from Tsarist-era systems. For example, our parliament is still essentially the same institution as was established for the Grand Duchy in 1906, many state organizations can trace their history directly back to that time (like the State Railways that were an independent Finnish "firm" since 1862) and some of the laws enacted during the Russian period are still around, though most often in amended form. On can argue that in the last 110 years, there has not been revolutionary changes here, only evolutionary ones.

One can well stretch that continuity back even to the Swedish period as in 1809 a lot of the framework from the Swedish system was retained here and never really replaced by Russian systems. Is Finland a "Taiwan" more for Tsarist Russia or to pre-1800 Sweden is then a good question...

For those interested in my above scenario on a joint Finno-Estonian Winter War, you can find the vignette I wrote here.
 
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I think that we can expect a lot of the Swedish-speakers to flee west in most scenarios where even the mainland of Estonia is taken over by the Soviets anyway.
Interestingly this fairly small populations had quite heavy contacts with Sweden, especially on religious matters. The Mission Covenant Church of Sweden had regular contacts with the Estonian Swedes, arranging meetings and summer camps on the isles. In the event of a proper war, I would guess they would be quite resourceful in saving Swedish protestants.
 
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