Kalev Stoicescu: Ukraine's future could follow Winter War scenario

Ukraine's potential fate under a modernized Winter War scenario is certainly worth considering. Whether a Continuation War will follow is another question, writes Kalev Stoicescu.
In the peace process initiated by U.S. President Donald Trump — whose latest milestones were the summits in Anchorage and Washington — two core issues are clearly at the forefront. These are territory and the separation line (the de facto border or line of control between free Ukraine and areas occupied by Russia), as well as the security guarantees to be provided to Ukraine. Of course, there are many other important matters that need to be addressed gradually.
There are indeed indirect parallels to the Winter War. If only Russia would change its attitude toward Ukraine — which, of course, takes time. Finland was part of Tsarist Russia for "just" 108 years, and even then, as a grand duchy, it enjoyed extensive autonomy. All of that ended 108 years ago when Finland gained full independence.
Ukraine was under Moscow's control for three times as long — around 330 years. The Kremlin never treated Ukrainians the way it treated Finns. Especially in recent years, thanks to Ukraine's determined resistance, the general Russian attitude toward Ukrainians has worsened significantly.
This does not mean, however, that a turning point might not come — when it becomes clearer to Russians that Ukrainians are ne naši (not one of us) and are going their own way. Westward. Spreading the narrative of the Winter War scenario may actually help Russians come to terms with the inevitable. Ukrainians, like the Finns once did, are bravely fighting for their freedom and self-determination. They have both the right and the strength to do so, along with many friends and supporters, and they will achieve their goal sooner or later — even if it means a de facto loss of territory and population.
Finland's fate after 1940
Stalin's Soviet Union attacked Finland on November 30, 1939, after Finland refused to comply with ultimatums from the aggressor — ultimatums which, much like today, were justified by "security concerns." True, World War II had already begun by then, but who helped unleash it? Naturally, Muscovy, which had signed the Molotov-Ribbentrop Pact with Nazi Germany. Just as Putin's Russia has entered into strategic partnership agreements with today's Axis of Evil states.
Moreover, Finland saw very clearly what was happening in Poland and the Baltic states. There were no illusions in Helsinki and the Finns decided to resist. The war lasted 105 days and ended on March 13, 1940.
The outcome was harsh for Finland, given that the country had fought virtually alone against an overwhelmingly powerful aggressor. The Soviet Union annexed around 35,000 square kilometers — about 9 percent of Finland's territory — including the Karelian Isthmus, areas near Lake Ladoga and the Salla and Petsamo regions, as well as (temporarily) the Hanko Peninsula and islands in the Gulf of Finland. Some 430,000 Finns had to evacuate occupied territories in haste and relocate to free Finland.
What followed was the Continuation War, which lasted from June 25, 1941, until September 19, 1944. Finland managed to reclaim its territories for about three years, as the Soviet Union was severely strained by the Nazi German offensive — including via Finland — but due to the armistice signed in 1944, Finland had to retreat to the 1940 borders.
Finland also had to comply with political conditions dictated by Moscow, a process derisively referred to as "Finlandization." Still, the country preserved its independence and — most importantly — its Western orientation. The Cold War ended, albeit only nominally, and Finland became a member of the European Union in 1995 and finally joined NATO in 2023.
The Winter War parallel to Putin's aggression against Ukraine is, in many respects, theoretical — given the differences in eras and circumstances — but from a historical standpoint, and considering the continuity of Muscovy's policies, it remains a compelling one. History has a habit of repeating itself in new forms. Ukraine's potential fate in a modernized Winter War scenario is certainly worth considering. Whether a Continuation War follows remains to be seen.
A free Ukraine belonging to both NATO and EU is possible
The conditions of the Winter War and Russia's aggression against Ukraine (February 2014–present) are, of course, in many ways different. There's no need to elaborate or analyze them at length — back in 1939, there was no NATO or European Union that could have restrained Stalin or provided Finland with widespread military and other assistance. Let alone a NATO and EU that would have included the Baltic states, Poland and other countries — and a democratic Germany that would have stood against Russian aggression.
What does merit consideration, however, are the core questions: territory, population and security guarantees. Finland was ultimately forced to retreat from the territories it ceded to Russia, despite its determined resistance. But Ukraine today is not (and likely won't be tomorrow or the day after) in a position where it must retreat further.
The issue now is factual, not legal, acceptance of territories already occupied by Russia. Roughly the same way a number of Western countries once accepted the reality of the Soviet occupation of the Baltic states — without ever giving it legal recognition. Finland, by contrast, was forced to legally accept its territorial losses in 1945.
Russia essentially took over empty lands from Finland, since nearly the entire population had been quickly evacuated to free Finnish territory. Ukraine didn't have the chance to do the same. Let's remember that in February and March 2022, the aggressor Russia managed to seize a large portion of Ukraine's border and coastal areas within a matter of weeks. Fortunately, Ukraine succeeded in pushing Russian forces out of many areas, including near Kyiv. Regrettably, Ukraine was unable to evacuate its population — some 5 to 6 million people, including those in Crimea — who were left at the mercy of brutal occupiers.
In 1945, Finland had no choice but to undergo decades of "Finlandization." Ukraine, however, has a clear perspective and real opportunities, however unpalatable that may be to Moscow. In the 1940s, Russia and Finland were more or less in a one-on-one confrontation, but the context of Russia's aggression against Ukraine and the peace process today is vastly different. Dozens of countries are involved — including the world's leading powers.
In the end, the narrative must convey to Russia — and to a much broader audience — that a modernized Winter War scenario is possible. Without a Continuation War and without Ukraine being "Finlandized." If Ukraine is prepared to accept the de facto control of occupied territories by Russia, then Russia must accept the full independence and self-determination of a free Ukraine.
If the Ukrainian people choose to join NATO and the European Union, then Moscow must accept that choice. A cease-fire and peace agreement that fails to offer Ukraine the best possible security guarantees is not acceptable. Russia's proposal of a "Budapest-2" involving China won't fly.
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Editor: Marcus Turovski










