What if there was an Estonian winter war?

What if there the Estonian government didn't accept the Soviet demands? Would Estonia lose or win? How would it influence the Finnish winter war?

This post was inspired by the Estonian alternate history book "Sügissõda" (Spring war) by Mart Laar
 
Depends bit would there still be war between USSR and Finland. Stalin might be bit better prepared for new war. But probably Estonia would lost badly altough Estonia has more defensible border. But such decision might affect to Latvia and Lithuania and they might come to help. Perhaps there would be some Finnish volunteers.
 
Estonia would get rolled over within a few days. Finland was extraordinarily lucky.

Finland was very lucky, namely in that Stalin sorely underestimated the Finns, and had his army attack them at one of the most inopportune times possible. The fact that Stalin believed an Allied intervention being realistic and almost imminent in early 1940 was also very lucky for the Finns as it convinced the USSR to stop the invasion and contend with a negotiated peace.

At the same time, though, Finland had a competent military, from the top leadership to the officer and NCO cadres, and down to the ordinary soldiers. It had a well-trained, large reserve. It was able to mobilize this military prior to the Soviet attack. And it could use good defensive terrain to its advantage, and prepared fortifications and defensive works besides.

The Estonian military had less advantages. The only thing in which it was roughly on the same level as the Finnish military was, I believe, weaponry and the supply situation, and even in terms of artillery and automatic weapons, it lagged behind the Finns who themselves had deficiencies in this area. While there was nothing wrong in the courage, fitness and willingness to fight of the average Estonian soldier (which many Estonians would prove fighting for the Finnish military in 1941-44 IOTL), I believe the general professionalism of the Estonian forces was lower than that of the Finns, on all levels. The top leadership was comparatively still fighting WWI in its strategic thinking, general war plans were not as good or realistic, and the field-worthiness of Estonian military formations did not reach the Finnish level.

In case of war, I think the Estonians had plans for mobilizing no more than two divisions of infantry. If I remember correctly what a young Estonian researcher told us in a recent conference, there were no actual plans for a fighting withdrawal. According to him, all the plans the Estonian military had were offensive, mind-boggling as that is. I believe there had been some 30s Estonian war games, followed by foreign observers, which had utterly failed to show the Estonian military as a competent force.

The Estonian terrain did not offer the defensive "bonuses" the Karelian Isthmus and the Karelian and Kainuu wilderness areas did. There were less natural obstacles, though Lake Peipus would still force the Red Army to use rather narrow avenues of attack at first, like north of the Gulf of Finland. This could be rectified by ferrying troops across the lake which I believe did not have serious Estonian naval forces or coastal defence. The Estonian border area had no prepared fortifications constructed before the war like there was on the Finno-Soviet border, AFAIK.

In the light of the above, I find it hard to see Estonian defence against the Red Army lasting longer than two weeks, even if the Soviets would initially underestimate their enemy. The deciding battle(s) would be fought on the isthmus between Lake Peipus in the south and the Gulf of Finland in the north. While the Estonians could maybe give a bloody nose to the first Soviet units crossing the border, their lack of the advantages the Finns had would mean that the Red Army could soon overwhelm them with their greater numbers, even if their attack would be as inept as it was during the Winter War against the Finns. Further Red Army troops attacking from the south side of the lake, or even across it, would put additional strain on the defenders who could not hold the enemy off for long. With no plans for orderly strategic withdrawal, the Estonian units would fight and die in place, or maybe even attempt a couple of suicidal (and ultimately futile) counter-attacks. Eventually they would break and flee in disarray, or be encircled.

A realistic guess might be that the Estonian frontal defences would fall in a week or at most in ten days, after which it would be a mop-up operation to put down remaining individual pockets of defence. There might be a last-ditch defence of the capital, a Battle of Tallinn, which would leave a part of the medieval town in ruins but would not cause a significant problem for the Soviet takeover of the small republic.

After organized resistance would end, there would still be various "Forest Brother" groups fighting in the countryside. The government (or parts of it), some of the military and a lot of civilians would flee south towards Latvia and by sea towards Finland and Sweden. An "Estonian People's Government" would promptly claim power in Tallinn and soon ask for the new Socialist Estonia to be incorporated into the USSR, as per "the will of the people". The Soviet crackdown against the pre-war Estonian state structures, civil society and bourgeois intelligentsia would be bloodier and more thorough than IOTL, though not catastrophically so, I believe - it was pretty bad as it was in our history.

Various butterflies would ensue. It is rather difficult to predict what this would mean for the Finnish will to resist Stalin's demands and fight. On one hand, Helsinki could see Estonia's fate in Soviet hands as a show of the hopelessness of fighting, and this might lead to the Finns accepting the upcoming Soviet territorial demands. On the other hand, the events south of the Gulf of Finland might also stiffen the Finnish resolve and create a popular reaction of "hell no, we won't give up without a fight" and lead to something like the OTL "spirit of the Winter War". Domestic Finnish issues, and things like the international (in general) and Swedish (in particular) reaction to the Estonian events might have a big effect on to which side the pendulum of national mood swings.
 
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