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Can Russia Still Win in Ukraine? What History Keeps Telling Us

Terminator Tanks
Terminator Tank from Russia. Image Credit: Creative Commons.

Six months into Russia’s “special military operation” in Ukraine, talking heads of all manner of political stripes and sympathies have debated ad nauseam about whether Russia can actually win the war.

My take as a lifelong student of military history, combined with my life experience in the military, is that it depends on how one defines “winning.”

It also pays to look at the historical precedence of past wars where the invading country had a clear advantage in manpower, materiel, and technology; I shall look at two such wars wherein Russia was the invader…and one involving the U.S.

Russia Should Think About The American Civil War (1861 – 1865)

We don’t have time right now to get into an acrimonious debate about whether the Union Army truly deserved to be labeled the “invader” or “aggressor.” What’s not debatable is the fact that the industrialized North had overwhelming on-paper advantages over the mostly rural South in terms of men, money, and resources.

Plus, there was Union Gen. Winfield Scott’s “Anaconda Plan” for choking off Confederate ports, not entirely unlike Russia’s current blockade of the Black Sea.

And yet, against all odds, for the first 3.5 years of the American Civil War, the South won most –though certainly not all — of the victories.

The Southrons had the “homefield advantage” so to speak, interior lines, and more. Moreover, to “win” the Civil War, the Confederacy simply had to hold out long enough and not lose; by contrast, the Union needed to attain total conquest in order to claim victory. We already know that Putin’s attempt to attain total conquest of Kyiv failed miserably.

Deadliest Guns of the US Civil War

Civil War Era Cannon Firing. Image Credit: Creative Commons.

Though we’re admittedly oversimplifying things here, that initial string of Confederate victories was due in large part to the Rebels’ more aggressive and audacious generals like Robert E. Lee and Stonewall Jackson, while the Yankees were accursed by generals with a case of “the slows” (as Abraham Lincoln himself put it), i.e., men like George B. McClellan who had impressive credentials but were unwilling to bring the total weight of the North’s numerical and industrial powers to bear. (Granted, some Civil War scholars like my personal friend Justin Mayhue and the late Prof. Joseph L. Harsh assert that McClellan has been judged too harshly by history, but that’s a debate for another time & place.)

It wasn’t until the Union promoted generals like Ulysses S. Grant, who was willing and able to match the Southrons’ aggressive fighting style, and, as cruel as this sounds to modern-day Southerners, military leaders like William Tecumseh Sherman and Philip H. Sheridan who had no qualms about waging “total war” against the South.

It should be noted that Abraham Lincoln had two distinct advantages that Vladimir Putin does not: (1) moral high ground and (2) lack of foreign intervention on behalf of the adversary. Both advantages were secured via at the Battle of Antietam in September 1862, which was enough of a strategic victory to (1) enable Lincoln to issue the Emancipation Proclamation – thus ennobling the Northern cause – and convince Britain and France not to come to the South’s aid.

Ergo, total conquest, if you’ll pardon the bad Southron-inspired pun, is a “Lost Cause” for Putin.

The Winter War (Russo-Finnish War), 1939-1940

Here’s an example I already touched upon on 21 May 2022 19FortyFive article about Finland’s Simo Häyhä, the deadliest sniper in history.

To reiterate what I stated then, this war began on November 30, 1939 (three months after the beginning of WWII, but before Hitler’s ill-advised invasion of the USSR) with the Soviet invasion of Finland, and t lasted until 13 March 1940.

Technically, the Soviets won the war, as the Finns eventually sued for peace and ceded significant territorial concessions to Josef Stalin, but it was very much a Pyrrhic victory for Moscow: somewhere between 50,000-15,0000 Soviet troops were killed in action, compared with 25,000 KIA the Finns. Of those Soviet KIAs, at least 542 were inflicted by the aforementioned Mr. Häyha AKA “The White Death.”

To elaborate further, accepting an armistice from Moscow cost Finland 11% of its territory, including the country’s second city of Vyborg. Yet, needless to say, Finland is still very much a free and vibrant country today. And to elaborate further on just how Pyrrhic the victory was for Moscow, we can examine the words of Nikita Khrushchev: “All of us — and Stalin first and foremost — sensed in our victory a defeat by the Finns. It was a dangerous defeat because it encouraged our enemies’ conviction that the Soviet Union was a colossus with feet of clay.”

So then, conceivably, one could envision Volodymyr Zelensky ceding Luhansk and Donetsk to Putin – but far less likely to budge on Crimea – to preserve his country’s remaining blood and treasure while preserving Ukraine’s overall independence and the majority of its territorial integrity.

As with “gaining” Vyborg in 1940, this would definitely be a Pyrrhic “win” for Putin.

Soviet Occupation of Afghanistan (1979 – 1989)

Even if Ukraine does concede Donetsk and Luhansk –and, for argument’s sake, even Crimea — to Russia, that doesn’t guarantee that anti-Moscow elements wouldn’t continue to wage a protracted guerrilla war in those areas…as we’re witnessing already.

The USSR’s experience in Afghanistan AKA “The Soviets’ Vietnam” shows that Russian troops don’t handle insurgencies in hostile foreign countries terribly well. As is the case with the Ukrainians, the Afghan mujahedeen resistance fighters were big-time beneficiaries of Western weaponry supplies. (For an exciting fictitious account of the CIA’s material support of the mujahedeen, read Ken Follett’s bestselling 1985 novel Lie Down with Lions.) And before any nitpickers out there start carping, yes, I know, Putin eventually did defeat the Chechen insurgency, but there’s a difference: Chechnya, its high degree of autonomy notwithstanding, is still Russian sovereign territory.

Russia's Putin

Russian President Putin. Image Credit: Russian Federation.

Russia Meets History: 

To sum up, Russia could conceivably still “win” in Ukraine under sufficiently scaled-back mission parameters and objectives, but other than Moscow’s wounded national pride and bragging rights, what would Putin truly gain from such a costly “victory?”

Russia Tanks

A service member of pro-Russian troops is seen atop a tank during fighting in Ukraine-Russia conflict near the Azovstal steel plant in the southern port city of Mariupol, Ukraine May 5, 2022. Picture taken May 5, 2022. REUTERS/Alexander Ermochenko

Christian D. Orr is a former Air Force Security Forces officer, Federal law enforcement officer, and private military contractor (with assignments worked in Iraq, the United Arab Emirates, Kosovo, Japan, Germany, and the Pentagon). Chris holds a B.A. in International Relations from the University of Southern California (USC) and an M.A. in Intelligence Studies (concentration in Terrorism Studies) from American Military University (AMU). He has also been published in The Daily Torch and The Journal of Intelligence and Cyber Security. Last but not least, he is a Companion of the Order of the Naval Order of the United States (NOUS). In his spare time, he enjoys shooting, dining out, cigars, Irish and British pubs, travel, USC Trojans college football, and Washington DC professional sports.

Written By

Christian D. Orr is a former Air Force officer, Federal law enforcement officer, and private military contractor (with assignments worked in Iraq, the United Arab Emirates, Kosovo, Japan, Germany, and the Pentagon).



  1. Neil Ross Hutchings

    August 28, 2022 at 11:01 am

    Thanks, a very good article with three good examples from history. I suspect whomever controls the Dneiper River water supply aqueduct will end up controlling Crimea. The Donbas, at least the majority of the land, seems lost now to Russia. The conflict now seems to be more about the potential hidden fossil fuel reserves on land and offshore.

  2. Jacksonian Libertarian

    August 28, 2022 at 12:36 pm

    “Captains should study tactics, but Generals must study logistics.”

    Combat Power rule of thumb: 1 smart weapon = 500 dumb weapons

    In all three examples above, the winning side’s logistics were superior. Sherman’s smashing of Confederacy logistics, Russia’s resupplied front, and the CIA + Pakistani supplied Taliban/Mujahidin.

    Logistics will also determine the Ukraine war. The West is supplying Ukraine with smart weapons, and anything else it needs. Russia on the other hand has burned through decades of accumulated weapons, and is reduced to using the huge stockpiles of ancient dumb artillery and ammo the Soviets laid down decades ago. Now that Ukraine is focused on destroying Russian logistics with smart weapons. It’s only a matter of time before shortages on the Russian front force them to retreat or surrender.

  3. from Russia with love

    August 28, 2022 at 6:23 pm

    The author is very selective about the story. what he remembers conveniently, what he forgets inconveniently… but I’ll remind you?
    relatively recently, Russia fought in Chechnya. unlike Ukraine, there really was an extensive network of terrorist cells, but they were suppressed two years after the end of the second Chechen war. this is only part of the truth, which is unpleasant for the West. Chechens are now the vanguard of Russian troops in Ukraine. the same will happen with Ukraine.

  4. Richard Pontone

    August 28, 2022 at 7:56 pm

    You should remember Brezhnev, then leader of the Soviet Union, thought his Invasion of Afghanistan would only last three weeks. His Foreign Minister thought it would end the USSR.
    Hitler thought that his Invasion of the USSR would only last four months. No Winter clothes were needed for his troops.
    Napoleon thought he could conquer Russia well before Winter started, and his Grand Army paid the price.
    Hannibal thought his Invasion of Italy would spell the end of Ancient Rome. No Siege equipment for conquering Rome would be needed.
    Yes, if Russia conquers the Southern coast of Ukraine, then they won.
    But Chechnya, Georgia, and Belarus sees their “God” can be killed as the Russian Army is a joke. No common sense Russian wants to die for “The Strategy of the Grandfathers”–a new term created by Russian soldiers.
    Remember the long game. There are 40 Million Ukrainians who will fight and die for their Nation and for the next 100 years.
    The Russians can’t match this Quantity and Quality of people power.
    Hannibal, nor Hitler, nor Brezhnev nor Napoleon could not match it either.
    History does not repeat itself. It merely rhymes.

  5. Putin is a terrorist

    August 28, 2022 at 9:56 pm

    How is he going to win a war using WWII junk against Western arms?

  6. from Russia with love

    August 29, 2022 at 5:31 am

    @Richard Pontone
    stop! ? but it was Western analysts who wrote that Russia would take Kyiv for nelya and capture Ukraine in three weeks, the Russian Defense Ministry never wrote anything like that, and Putin too. you want to say that the fate of Napoleon and Hitler is destined for the Western coalition?

    “There are 40 Million Ukrainians who will fight and die for their Nation and for the next 100 years.” ie you priznaesh that the US and the EU finances and arms the Nazis? amazing revelation?? it means Russian propaganda is absolutely right – Russia is destroying Nazism in Ukraine.?
    and the question arises about 40 million. are you really going to fight with Russia to the last Ukrainian? Are you going to kill all women and even babies? you are a real sick bastard ?? for reference, about 10 million Ukrainians have already fled to the EU. you demand that they die standing in the cold in shorts drenched in red paint, somewhere on the square in front of the elf tower? how it will harm Russia?
    do you believe that all Ukrainians really want to die for YOUR Ukraine? you need to come up with an explanation why there are no queues at the recruiting offices in Ukraine. you need to figure out why the employees of the Ukrainian military registration and enlistment offices are forced to patrol the cities and catch men of military age. you need to figure out why Ukraine adopted a law on imprisonment for 10 years for refusing to mobilize. and you need to think very hard about how efficient the army will be, assembled from people who were forcibly, under the threat of prison, driven into this army.

  7. Stefan Stackhouse

    August 29, 2022 at 10:02 am

    Russia is not going to “win” by any definition in 2022.

    Will Ukraine continue to exist as an independent entity in 50 or 100 years time, though? That is the thing about Russia: they are there, they are big, and they will keep at it, year-after-year and decade-after-decade. Many are the nations that were initially successful in their defiance, but are now former nations, lost to the dustbin of history. The jury will be out for quite a long time on whether Ukraine will ultimately join them.

  8. mawendt

    August 29, 2022 at 1:14 pm

    It’s not a question of Russia ‘losing’ – now, it’s a measure of by how much they will lose.

    1. Ukraine showed the world the the incompetent Russian military sucks royal balls in warfare. Even before Western equipment arrived.

    2. The war emptied Russia’s treasury so that they are reduced to selling oil at a huge discount and making very painful long term deals. It’s never a good thing to create that dependency with… China.

    3. Europe has solid reference regarding Russian energy supply, and is weaning themselves off it.

    4. It’s not the war, and not even the ‘victory’. Russian soldiers will return bitter, families of Russian casualties will hate, and Russian governance will be difficult. Many Russian soldiers, and prolly a good portion of the Russian civilians, don’t want to be a part of this war. It shows on the battlefield.

    5. If the conflict continues in the same manner as present, Russia will lose, slowly and painfully for both sides. But lose they shall – militarily, in domestic politics and economics, and in international relations. For at least a decade.

    6. I’d guess nearly all of Russia’s Western border nations, and NATO members, will be improving their military manpower, equipment and ordnance based on what they analyze of Russian tactics and equipment. Plus, NATO new member states. Yep. Just what Russia wanted – to stop that NATO expansion, and keep it weak. Fail.

    7. If Russia takes the land, Russian-speaking Russian-looking Russian-acting insurgents will take the war to Moscow city for 20 years. Tell me that’s a trade off.

    8. If the war ends tomorrow, Russian will need at least a decade and maybe two to resupply the material, weapons, and equipment that has been destroyed. Russian military has been crippled.

    9. To win, Russian needs a combat factor of about 10 times Ukraine’s combat power. It has about three on the line. Russia cannot win like this. To win, Russia needs about 1 million soldiers with their equipment, and AIR POWER (something not yet risked so much yet). Russia has about 200,000 on line now. That is a defensive-attrition line, not a serious army of victory. Let’s just say the politics of forcibly calling up and arming a million unhappy soldiers in the present Russian political environment would not be… good.

    Time does not favor the Russian.

  9. OIF Combat Vet

    August 29, 2022 at 2:25 pm

    Ukraine is a money pit, and the sooner it is over the better.

  10. Putin is a terrorist

    August 29, 2022 at 5:53 pm

    Ukraine Army has shown remarkable strength, versatility and creativeness. Couple their commitment to their country with Western weapons and Putin is in deep shit. Russian soldiers don’t want to be there and many have refused to fight. Perhaps they don’t like having rusty WWI rifles that jam? Jack in the box tanks are a nice touch, though. Gives them confidence they’ll return to the shithole Russia…in a body bag.

  11. iGreg

    August 29, 2022 at 11:59 pm

    “what would Putin truly gain from such a costly “victory?”

    Russia is winning: 1. The west has been weakened substantially with European countries suffering a major energy crises, which could lead to major instability come winter. 2. Russia holds more territory in Ukraine than it did prior to the invasion. 3. Former Soviet satellite states are scared. 4. Everybody has been predicting that Putin is dying, and he is not dead, making Western news and intelligence sources look stupid (which they are).

  12. Len Mullen

    August 30, 2022 at 2:13 am

    No ‘Super Power’ has won a war since WWII. You cannot win unpopular wars — especially when leadership lacks the will to do ‘whatever it takes’ to win. Time to end the endless wars.

  13. Ukraine

    August 30, 2022 at 5:12 am

    Define: “Win”

    The most likely result at this point is a negotiated peace in which Russia keeps virtually all of the territory it is currently occupying. That includes all of Crimea.

    So, Russia gets about 20% of what used to be Ukraine.

    Its a lot less than what Putin thought he might get when he invaded, but that’s still a WIN for Russia.

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