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Why Russia Can’t Seem to Win in Ukraine: Study the Winter War of 1939

Russia vs. Ukraine
Russian military drilling with artillery. Image Credit: Creative Commons.

Russia’s invasion of Ukraine has left the media grasping for parallels. Mechanized wars of maneuver spanning entire countries have, fortunately, become rather rare. But at least one conflict from the 20th century may hold some lessons as to the political nature of the conflict. The Winter War, forgotten by many as an appetizer to World War II, remains firmly in the memories of the Finnish people who bitterly resisted a vastly superior Soviet force for several months.

Russia vs. Finland: The Course of War

In the winter of 1939, the Soviet Union invaded the eastern marches of Finland. The invasion was part of the agreement between the USSR and Nazi Germany to partition Eastern Europe.  Finland had seceded from the Russian Empire in the waning days of World War I, and unlike Ukraine, the Red Army had not reconquered its territory.  However, Josef Stalin regarded the USSR’s position in the north as precarious and was particularly concerned about the proximity of Finnish territory to the city of Leningrad. Historians differ with respect to the magnitude of Soviet expectations, with some suggesting that Moscow sought regime change and others that neutralization and territorial adjustment were the goals.

The Soviet attack began on November 30. The Finns rapidly retreated to a set of prepared defenses known as the “Mannerheim Line” after a Finnish defense chief. The extreme cold took its toll on under-prepared Soviet troops. Poor Russian tactics resulted in little-to-no cooperation between infantry, armor, and artillery, just as bad weather limited air support. For their part, the Finns fought well from defensive positions and used innovative guerrilla tactics (including ski troops) to disrupt and destroy Soviet detachments. The Finns also invented (or at least coined the term for) the “Molotov cocktail,” an improvised grenade named after the Soviet defense chief that could be produced by civilians. Soviet military results were dreadful.  Poor Soviet morale even at the outset of fighting declined into absolute mutiny, with Red Army infantry refusing to advance against prepared Finnish positions. Fighting ground to a halt in late December, and the front remained quiet for most of January.

Russia Marches to Victory

Soviet forces reorganized themselves and prepared for a new offensive that would begin in February. The Soviets opened a massive artillery barrage on February 1, inflicting severe damage on Finnish fortifications.  On February 11 a combined arms offensive created a break in Finnish lines. Finnish fortresses along the Mannerheim Line had been battered and were progressively abandoned in the face of a renewed assault. Finland had hoped for assistance from abroad, making appeals to Sweden, France, Britain, and Germany, but only minimal support was forthcoming. Germany allowed the transit of weapons to Finland, but Hitler had no interest in antagonizing Stalin on Finland’s behalf. Sweden allowed several thousand volunteers to travel to Finland in order to fight, but ruled out formal participation. Britain and France expressed strong support for Finland and even developed several schemes for deploying troops (this would have put Paris and London at war with Berlin and Moscow at the same time), but the Swedes declined permission to transport troops and equipment.

Faced with an unwinnable situation, Finland sued for peace at the end of February. The war lasted another two weeks but ended with significant Finnish territorial concessions. Some 25,000 Finns died, along with something between 50,000-15,0000 Soviet troops. Finland would renew the war by joining Nazi Germany’s Operation Barbarossa in June 1941, but Finnish fortunes fell with those of their partners and Finland again sued for peace in September 1944.

Parallels to Ukraine?

As we acknowledged at the beginning, all parallels to the current war in Ukraine are inexact. Moscow’s ambitions in 1939 were not nearly as maximalist as Putin’s declared intentions with respect to Ukraine, as the USSR had no expectation that it would replace the government in Helsinki. Thus, the outlines of peace were apparent from the beginning of the conflict.

However, the conflict is interesting in the context of the performance of the Russian army. The Red Army began the Winter War disastrously, advancing with poor morale and poor training against an opponent far more enthusiastic and skilled than the Soviets had anticipated. Having been handed a devastating series of defeats, the Soviets picked themselves up, re-organized their forces, and committed to pressing forward. Russia was willing to pay huge costs for the relatively minor territories it won and began to reorganize its armed forces along the way. The Ukrainians have not handed Russia a defeat on this scale, but we still may see significant changes in how the Russian military operates over the next weeks and months.

Russia’s Winter War of 2022?

The course of the Winter War offers a hopeful lesson for Ukraine, in that it is possible for a smaller country to badly bloody Russia’s nose. Ukrainians are already preparing Molotov Cocktails in preparation for urban fighting in Kyiv and Kharkiv. Another lesson is less hopeful; Russia picked itself up off the canvas, shook off the damage, and proceeded to pound Finland until the Finns could take no more.  Given the maximalist demands of the Russian government, the pain inflicted on Russia so far, and the extent of Russian territorial success (especially in the south), Ukraine may be looking into a grim future, the optimism of the moment notwithstanding.

Now a 1945 Contributing Editor, Dr. Robert Farley is a Senior Lecturer at the Patterson School at the University of Kentucky. Dr. Farley is the author of Grounded: The Case for Abolishing the United States Air Force (University Press of Kentucky, 2014), the Battleship Book (Wildside, 2016), and Patents for Power: Intellectual Property Law and the Diffusion of Military Technology (University of Chicago, 2020).

Written By

Dr. Robert Farley has taught security and diplomacy courses at the Patterson School since 2005. He received his BS from the University of Oregon in 1997, and his Ph.D. from the University of Washington in 2004. Dr. Farley is the author of Grounded: The Case for Abolishing the United States Air Force (University Press of Kentucky, 2014), the Battleship Book (Wildside, 2016), and Patents for Power: Intellectual Property Law and the Diffusion of Military Technology (University of Chicago, 2020). He has contributed extensively to a number of journals and magazines, including the National Interest, the Diplomat: APAC, World Politics Review, and the American Prospect. Dr. Farley is also a founder and senior editor of Lawyers, Guns and Money.



  1. Alex

    March 3, 2022 at 8:50 pm

    What does it mean to win? Russia has a clear plan: the demilitarization and denazification of Ukraine. If you look at the real map of hostilities, you can confidently say that Russia is achieving its goals. Why this stupid propaganda?

  2. William Patton

    March 3, 2022 at 11:51 pm


  3. Jacky

    March 4, 2022 at 12:05 am

    The 1939 winter war is not relevant to today’s battkefield scenario.

    In 1939, soldiers used bolt action rifles which were more like hunting rifles, not modern warfare firearms designed for mass firepower.

    Today, on the modern battlefield, soldiers need to direct mass firepower onto the enemy quickly, to secure ground.

    Even in the air, soldiers or combatants usually direct volleys of fire at opponents as seen in past middle eastern wars, with several missiles homing in on an enemy aircraft each time it comes within range.

  4. Ww2 historian

    March 4, 2022 at 1:33 am

    War, war never changes

  5. War photographer

    March 4, 2022 at 1:49 am

    Victory for russia would come at genociding the entire ukranian people…including genociding j’s

    A survivor of lenigrad in ww2 was protesting and was arrested…

    Even if russia takes over all of ukraine just like the afghanistan, it doean’t mean victory.

    Even if they kill all these “nazis” and put in a puppet…the people will rise up and kill them…

    Ukraine now hates russia as much as russia hates nazis…putin is delusional to think people whose families he has just slaughtered will love him magically…

    This will not end well for russia at all. Foriegn fighters will use bases in neighboring countries like bases in pakistan in afghanistan and flood ukraine indefinitely doing insurgency…

    There will be an endless supply of manpower this way…not even russia can beat that…also ukraine hasn’t mobilized all thier reserves and men quite yet…100s of thousands still organizing into platoons and doing quick 2 week training…

    Ukraine already within a week has 15k foriegn fighters…each week will grow in intensity…we could see 50k fighters flooding ukraine each week endlessly…

    Afghanistan only had 15% of its pop rise up qhen soviets invades…ukraine has 95%…and the foriegn fighters…

    Grandmas are driving tanks and throwing molotovs ffs…how is russia gna beat this? They can’t…it is impossible unless you genocide and do a war of annihilation…

    Nazi germany was in the exact same spot..against the entire country of russia…

    This will go for 10 years and cost russia 100k to 200k troops…trillions in munitions and equipment they’ll never replace cause thier economy is gone…

    Stock market crashed…ruble crashed..

    I notice the neo-soviets are using the same tactic as in afghanistan taking over just the roads…not going into the country side…they’re too scared to

    It is a terrible tactic that leaves them wide open for mass insurgency…

    All russia is getting are the roads here…thats not conquering…thats hiding in a den of snakes…

    Even tho tgey are in kherson…its the south port..not the entirity of it…and ita becoming ratzkrieg…urban fighting with guerilla tactics…

    Ukraine also just retook back bucha…they are able to do large offensive ops…

    Russia is doomed in the long run…ya sure they may bare thier weight down…but its gna break russia doing so…they will only end up with body bags in the end…

  6. Frej Holmberg

    March 4, 2022 at 4:05 am

    I think thqt I should point out, that the Soviets did indeed aim for a total conquest in a similar way as today. They had orders to not cross the Swedish border by mistake. A Finnish SSR was declared in the first conquered town (Terijoki). And political comissars were apparently confused why the Finns resisted so much, both countries having been peacefully together a few decades earlier.
    Also, the way in which Soviets attacked without smart dupply organization mirrors the situation today.

  7. Stefan Stackhouse

    March 4, 2022 at 10:18 am

    It is a sad and tragic reality that geography has dealt the Ukrainians an even worse hand than it did to the Finns. They live on flat and indefensible terrain, but terrain that is of much more strategic importance and economic attraction to Russia than Finland ever could be. Even trees for soldiers or partisans to hide behind are few and far between (unlike in Finland). Short of a massive and sustain effort to militarize and prepare their entire population well in advance (an effort that, unfortunately, was never attempted until too late), there never was any realistic prospect that they could successfully resist and repel a determined Russian attack.

  8. Chris Roach

    March 4, 2022 at 12:47 pm

    A very thoughtful analysis. It helps in life and in foreign policy to be able to see things through the eyes of one’s opponents. The morality play about Ukraine only makes sense if the last eight years and the last 25 are completely ignored.

  9. Alex

    March 5, 2022 at 4:59 am

    Russia’s special operation in Ukraine has not been completed. but already there are similar articles of those who are trying to predict the future. This is at least not professional, but at the maximum – just propaganda.

  10. Mr Me

    March 28, 2022 at 3:02 pm

    More propaganda as usual easily identifiable,Russia is doing exactly what they need to do and not according western intelligence or media standards.

  11. JEF

    April 14, 2022 at 10:34 am

    During the Warsaw Ghetto uprising a handful of Jews held off a well-armed German army with molotov coctails and handguns. i.e. the simplest ‘well-armed militia’ is all it takes to avert and resist the war mongers in our world. Ukraine has been a sitting duck for years doing nothing to arm itself/its people while Putin glared/awaiting his best time to make his obvious move. (Today, Taiwan does the same). Arm!: it has always been the world we live in. Humans seem to be an aggressive territorial species. see: Israel. see: The Second Amendment (US Constitution).

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