Putin's massive mistake: Lawrence Freedman on Ukraine and the lessons of history

Putin made bad decisions based on "total misapprehension," says military expert. Now the whole world pays the price

By Chauncey DeVega

Senior Writer

Published November 21, 2022 5:45AM (EST)

Vladimir Putin | A destroyed tank lies in rubble, in central Mariupol (Photo illustration by Salon/Getty Images)
Vladimir Putin | A destroyed tank lies in rubble, in central Mariupol (Photo illustration by Salon/Getty Images)

Since the Russian invasion last February, the Ukrainian military has spent months trading space for time. That has proven a successful strategy: U.S. and NATO military assistance, excellent civilian and military leadership, a determined and well-trained military and a population committed to total resistance has evidently turned the tide against the Russian forces.

The Ukrainian military first pushed the Russians back from the attempted siege of Kyiv. In late August and September, the Ukrainians launched a series of bold offenses in the northeast and southeast, liberating a considerable amount of Russian-occupied territory, including the strategically important city of Kherson. But these battles have been costly for both sides. The Ukrainians have lost many thousands of soldiers and expended a large amount of their artillery supplies, particularly the precision-guided, long-range U.S.-made munitions that have been integral to interdicting Russian supplies, targeting command and control, and generally creating chaos behind the front line areas.

The Russians have suffered far worse losses: Western intelligence agencies estimate that the Russian military may have suffered more than 100,000 casualties, and has seen its most modern and elite units decimated. Russia has also lost an unexpectedly high number of its best attack helicopters and fighter aircraft, making it even more difficult to turn back the Ukrainian offensive.

With winter arriving, it would be normal for the two armies to rest, consolidate their gains and prepare to fight again in the spring, especially in terrain where snow and mud will make maneuvering difficult for several months. So far, the Ukrainian military is defying those precedents, as it continues to attack Russian forces and reclaim lost territory. In response, the Russians are launching local counterattacks, digging in and bringing forward new conscripts to replenish their demoralized frontline forces. The Russians are also using drones and missiles to attack Ukraine's infrastructure and major cities in an attempt to break the Ukrainian people's will to resist by denying them heat, clean water and electricity.   

The war in Ukraine is far from over and it would be foolish to make firm predictions about its outcome. But one thing is assured: This war will be studied for a long time as a type of lethal classroom where decades-old or centuries-old principles of strategy and tactics are being tested by the realities of the 21st-century battlefield.

Lawrence Freedman is one of the world's leading experts on foreign policy, war, strategy and international relations. He is emeritus professor of war studies at King's College London and the author of many books, including "Strategy: A History," "The Future of War" and "The Evolution of Nuclear Strategy." His new book is "Command: The Politics of Military Operations from Korea to Ukraine." Freedman's essays and other writing have been featured in such publications as Foreign Affairs, Foreign Policy, the New Statesman and the Times (U.K.).

In this conversation, he explains how the Russian military disregarded the fundamental basics of military strategy in its war against Ukraine, which is why Russia faces defeat on the battlefield. Freedman also contends that, contrary to Vladimir Putin's assumptions, in attacking Ukraine he strengthened that nation's resolve, sense of national unity and will to resist. This is especially true of the terror bombing campaign against Ukraine, which Freedman argues will do little or nothing to advance Russia's strategic goals or win the war.

Freedman also ponders counterfactual scenarios about the Ukraine war. How would a general from another time period adapt to modern warfare as seen in Ukraine? What would they do differently, or do the same? Freedman also takes on a question that has been much discussed online and in other forums: What would happen if the Russian military directly engaged in battle against U.S. or NATO forces?

Toward the end of this conversation, Freedman explains that Vladimir Putin's failures in Ukraine are an example of a larger dynamic: Authoritarian and autocratic leaders consistently make poor decisions because they are insulated from reality and accurate information.

How are you making sense of the war in Ukraine? As a military historian, how do you process these events on a human level?

I have very mixed emotions about the war. First, I always feel a bit guilty because my life gets more interesting and enthralling, in a way, whenever something awful is going on. Wars make me busy. It would be nice if peace made me quite as busy. I have Ukrainian friends, and what they are going through is awful. But on the other hand, they've shown enormous resilience and have made remarkable progress in fighting the war. In the end, I hesitate to say that I am optimistic because it is dangerous to predict the future. Yes, the Ukrainians have the initiative in the war. But even then, more people are going to die, be made into refugees, and generally life is going to be hard for the Ukrainians for the foreseeable future. 

What does it mean to be Ukrainian right now?

I have spoken to a number of Ukrainians about this question. My feeling is that they are experiencing a much stronger sense of national identity than before the war. The idea that the Ukrainians were distinct from Russia is not that new. But I think what's striking about their sentiments now, and we see it in all the polling, is that there is a much clearer sense of solidarity with each other and a belief in the state and in Ukraine's leaders.

How do you balance your intellectual interests and curiosity about war and armed conflict with seeing the human cost and reality of it?

I have followed a number of wars pretty closely throughout my long career. I try not to look at wars as some type of spectator sport: War is about violence. The war in Ukraine is different in several ways. First, the Russian tactics are clearly very brutal, as they were in Syria. The amount of information about what is happening day to day in Ukraine is much more, as compared to previous wars. What we can see about war is just much more immediate and intimate.

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I started paying close attention to wars with the Falklands in 1982. The amount of information that was coming back at any time was very small. There was radio commentary and very little television coverage of the Falklands — and even that was out of date. With social media today and the internet I can see tanks being blown up and actually watch the soldiers scurrying away, trying not to die. This is unprecedented in many ways. It is all so much closer than before.

A person can literally watch the war in Ukraine in real time. It is dystopian, it feels like a science fiction movie. To me, it's very unsettling. Our culture is already violent enough without that level of desensitization.

Vietnam was described as the first television war. I remember the Tet Offensive in 1968, for example. There was an immediacy in the coverage of the war as long as the TV crews were there to transmit images in near-real time, which meant, as in Tet, that fighting was taking place in cities. For a lot of the time this was about counterinsurgency, as also in Iraq and Afghanistan. What is unusual about the war in Ukraine is that this is a conventional war, and one fought at high intensity This isn't a walkover. This is a very serious fight for both sides. Yes, there was all the media coverage of the Gulf War in 1991, but no one really thought the United States was going to lose.

But we should still be careful in how we understand all this footage coming back from the war in Ukraine because we are not seeing everything, and the coverage is inevitably selective by nature.

When you look at the war in Ukraine, what is the simple story, and what is the more complicated one?

The initial assaults by Russia failed because of arrogance and an underestimation of the Ukrainians. The first moves by Russia failed, and they never really recovered from that.

The simple story is quite straightforward: Putin ordered his military to invade Ukraine on the basis of a total misapprehension of the country he was taking on. It was that error — presuming the country to be an ineffectual non-state ruled by an illegitimate government — which was used to justify the invasion in the first place. The reason the initial assaults by Russia failed was because of arrogance and an underestimation of the Ukrainians. The first moves by Russia failed, and they never really recovered from that. The Russians could not take Kyiv, and then we had the stage where they moved to the Donbas region. Western support started to come in and that moved us to the next stage of the war, from late July and August to the present, where the Ukrainians are taking the initiative because they have better equipment and supplies from America and NATO.

What is happening now in the war is very much the consequence of the Russians suffering shortages in manpower because they expended them — quite carelessly, in my opinion — early on. The Russians are pretty thinly defended now and are trying to bolster their ranks through mobilizing reserves and a de facto draft. The Russians have gradually become a 20th-century army, while the Ukrainians are gradually becoming a 21st-century one.

On another level, we are seeing a coercive Russian strategy against Ukrainian society. This involves a wide range of war crimes. Russia is also trying to turn off the power and electricity in Ukraine. The Ukrainians cannot do the same against the Russians in terms of targeting infrastructure. The Ukrainians are winning on the battlefield, but they cannot hit back against the Russians on that strategic level.

The Russian military has been exposed as a hollow force. Before the war in Ukraine, it had a fearsome reputation. Now the Russian military looks like it may collapse in Ukraine. Are there other historical examples of such a thing?

It does happen that armies, when they are properly tested, just collapse. It's not wholly unusual. That can happen because of a lack of supplies or from poor leadership. The Iraqi army in Desert Storm is an example of this. Before Desert Storm, the Iraqi army was talked about as the fourth-largest in the world, battle-hardened from their war against the Iranians. The Iraqis believed their own reputation. But in the end the Iraqi military could not oppose the combat power of the United States.

As for Russia, they did quite poorly in the first Chechen war. They went in arrogantly and got hammered by the Chechens. But that was explained as being caused by the end of the Cold War and a lack of funding for the Russian military, which was demoralized. Russia had time to rebuild its military afterwards, and it was assumed they had used the money from oil to modernize their forces.

Putin was misled by the fact that their recent military operations were successful, such as in Chechnya, Georgia and in particular in Crimea. That led him to believe the Russian military was competent and professional.

I believe that Putin was misled by the fact that their recent military operations were successful, such as the second Chechen war, their intervention in Georgia and, in particular, taking Crimea and bullying the Ukrainians in 2014, followed by their actions in Syria. This led Putin to believe that the Russian military was competent and professional. Of course, that turned out to be incorrect. Moreover, the war in Ukraine is on a different scale. The Ukrainians are professional, motivated, well-trained, determined and are fighting back in a sophisticated and effective way. The Russian military was not prepared for such opposition.

What is new about what we are seeing, in terms of the operational art of war in Ukraine? What is old? 

Much of what is taking place in Ukraine would make perfect sense to a World War II commander. Drones, the communications technology, the intelligence-gathering technology and the satellites would be quite awesome to them. But the basics of attrition and maneuver and of where you hold the line and where you don't hold the line, especially the importance of logistics, are timeless. On that point, the Russians have really encountered problems with the basics of logistics. Keeping supply lines open is just fundamental to war.

The war in Ukraine is on a much smaller scale than what we saw in World War II. But the fundamentals are much the same. What is different from previous decades, and World War II in particular, is the precision of modern weapons. The Russians had a number of precision-guided weapons, but they did not use them effectively in the early stages of the war. Instead of hitting military targets, the Russians used them against civilian targets. That was painful for the Ukrainians, but it did not actually help Russia on the battlefield.  By comparison, the Ukrainians have used the American HIMARS system and other long-range weapons to focus on specific targets of value, as opposed to the Russians. The Ukrainians have learned to use drones and other intelligence assets and specific targeting information very effectively. It really is quite impressive.

Many different narratives are being imposed on the war in Ukraine. Many of them are premature. One I have been following closely in the mainstream media is that Javelin and other ATGMs have somehow made the tank obsolete. That is an old and repeatedly disproved claim. What are your thoughts?

The tank has always been a subject of debate. For example, in the Arab-Israeli war in October 1973, many tanks were lost. How? From other tanks. The main anti-tank weapon is often another tank. The fact is, if you want to move a distance with firepower and have a degree of protection over difficult terrain, it is going to end up looking like a tank. Anything can be vulnerable on the modern battlefield, because if you can be seen you can be hit. That having been said, you still need to move people and firepower on the battlefield. Of course there are forms of deception and finding cover and using artillery and infantry to screen and protect your forces from short-range anti-tank systems. 

This is why combined arms is critical on the modern battlefield; every system has a role to play. You can't isolate the tank and say that it's gone and everything else stays. There is always going to be a role for tanks. Will the balance of systems on the battlefield change in the future? Of course. UAVs [unmanned aerial vehicles] are now being used instead of manned aircraft for certain missions. But that doesn't mean you get rid of manned aircraft, because they can do things that a UAV can't. You use the best system for the mission.  

Russia is waging a terror campaign using drones, missiles and artillery against Ukrainian cities and infrastructure. What do we actually know about the effectiveness of targeting civilians as part of a larger strategy to win a war?

Unfortunately, we know a great deal about this. This is a political question about terrorizing populations and whether to do so or not. The question is: Does targeting civilians and population centers actually make the public turn on their own government?

The Allies during the Second World War did terrible things against German cities, especially toward the end. But there wasn't much that the German people could do about it. They lacked the means to change their government. In the case of Ukraine, there's absolutely no evidence that the attacks on civil society have made a difference to popular support, if anything, the Russian attacks have encouraged popular support for the war. Attacking civilian populations can backfire in that way. Terror bombing and attacking civil society does not necessarily gain the attacker a political victory.

What are some of the main things the Russian military has done incorrectly in the execution of their war in Ukraine? By comparison, what have the Ukrainians done right?

The Russians' main error is that they strategically underestimated their opponent. That is always a basic mistake: Never underestimate your enemy. The Russians also did not have enough infantry and manpower, more generally. They do not give enough autonomy and flexibility to junior officers and others lower down the chain of command to make decisions, improvise and address problems.

The Ukrainians have not wasted weaponry. They have thought hard about the targets they need to hit. Their ability to maneuver and encircle the Russians has caused them to panic.

The Russians also failed to anticipate what the Ukrainians could do with accurate artillery. The Russians didn't disperse their ammunition enough. The Russian logistics system was too rigid, which makes it an easy target. What did the Ukrainians do right? They delegated initiative to quite small groups of forces and junior officers. The Ukrainians had to rely on taking the initiative against the Russians; that was central to their strategy and tactics.

The Ukrainians have not wasted their weaponry. They have thought hard about the targets that they most need to hit. When possible and where it made sense, the Ukrainians have used maneuver warfare to encircle the Russians rather than go directly at them in frontal assaults. The Ukrainians' ability to maneuver and encircle the Russians has caused them to panic — it'a demoralizing. In total, the Ukrainians have waged a very astute campaign against the Russians.

Armchair generals and other students of military history love counterfactuals and "what if" scenarios. One of those scenarios we see in response to the war in Ukraine is that the U.S. military and NATO would easily destroy the Russians in a conventional war. I am suspicious of such a conclusion, because in my opinion the Russian military and its leadership would approach such a scenario much differently than they did with Ukraine. How do you assess that counterfactual?

We just don't know. Counterfactuals are useful for testing theories of causation. What variable made the difference? If the Russians genuinely thought they were protecting their homeland, what we are seeing with Ukraine might have turned out differently. The Ukrainians are much more motivated in this fight than the Russians. Nuclear weapons are a variable here too. If the Russians really did think they were fighting for their own territory, they'd be much more likely to use nuclear weapons if they were losing. I am of the mind that the Russians still won't do such a thing in this conflict. Those types of questions can be explored using counterfactuals.

Autocrats tend to make bad decisions. They believe in the possibility of big, bold, decisive moves, and they don't have people who dare to warn them about all that can go wrong.

To answer your question, in a straight fight between the Americans and the Russians, the Americans would have won. American equipment, supplies and overall forces are just that much better. One of the surprising things about the war in Ukraine is the limited impact of Russian airpower. By comparison, the Americans would dominate the battlefield with their airpower — or at least would try to do so. We reasonably assumed that the Russians would do this in Ukraine. They weren't able to do it. If the Russians cannot dominate the Ukrainians with airpower, they would not be able to do it against the Americans.

The United States does not lose conventional battles very often. The United States does have difficulty with insurgencies, because in the end it is not worth the effort. Americans get impatient. In the end, the Americans would not have had much trouble with the Russian military that we are seeing in Ukraine.

What are some of the lessons from the war in Ukraine for NATO members and European militaries?

The Americans are going to fight in all domains. The British, the Germans and the French, for example, are not going to fight in all domains in the same way. They must think as an alliance: The European countries are not able to do everything on their own. A huge lesson from the war in Ukraine is that the intensity of modern warfare means you go through material and supplies very quickly. The stockpiles are never sufficient. The NATO countries have greatly depleted their supplies supporting Ukraine. 

That means more resources are going to be put into building back up supplies. This means more ammunition, shells, rockets, missiles and the like for the future. This is not a new lesson, but it has to be relearned. Logistics are critical because even if you are making more ammunition and other supplies, you still have to get it all to the front. 

Your new book focuses on command and leadership. What does the war in Ukraine tell us about Vladimir Putin?

Autocrats tend to make very bad decisions. Democracies make bad decisions too, but the difference is that autocracies believe in the possibility of big, bold, decisive moves, and they don't have people who dare to warn them about all that can go wrong. There are sycophantic advisers who don't dare to criticize the autocratic leader. This can cause horrible outcomes. 

What's happened in Ukraine is a good example of how autocrats make mistakes. This war was Putin's decision. Putin had a theory about Ukraine, and did not confirm that theory with real experts who would tell him that he was wrong. Putin believed that Ukraine would crumble if pushed hard enough, and that turned out to be very wrong. 

By Chauncey DeVega

Chauncey DeVega is a senior politics writer for Salon. His essays can also be found at He also hosts a weekly podcast, The Chauncey DeVega Show. Chauncey can be followed on Twitter and Facebook.

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