What if, somehow, the winter war was even worse for the Russians? What if Finland was able to win the Winter War?
Not really possible given the size and power difference between the two. OTL Finland was stretched pretty much to the limit from my understanding just holding out for as long as it did. Stalin isn’t going to take a black eye, shrug, and go ”Ok, guess you got me, time to go home”. Accepting a Finnish win is just too big of a prestige hit.What if, somehow, the winter war was even worse for the Russians? What if Finland was able to win the Winter War?
The available Finnish trained manpower was running low - at the beginning of the war theThe Finns might have been able to win in March with a better supply of artillery and ammunition. Considering the numerical disparity, this may have been one of the most important considerations. If Stalin isn't satisfied with the results of the March offensive, the Soviets really can't do anything until June, after France has fallen. I don't know if that would make a difference for Stalin, but a longer war could have important impacts on Finland's diplomatic situation, like an Anglo-French intervention in spring.
While CanKiwi's timeline has been well researched, in my opinion it still suffers from couple of problems.There's an old timeline that's sporadically updated these days that's about if Finland had done it's best to prepare for a war with Russia after independence.
You can check it out. It's a good read, even if it's a lot of text.