Vladimir Putin fancies himself a great student of Russian history. He couched his justification for the invasion of Ukraine in a vision of Russia and the Soviet Union’s history that was paranoid, grandiose and incoherent, all at the same time. Ukraine needed to be subjugated by Russia because it was acting as a stalking horse for NATO and the West. At the same time, the West was declining and Russia had the strength to, in Putin’s mind, reincorporate Ukraine into its natural place within a Russian empire. Clearly, Putin has decided that this was the right moment to establish himself as one of the greatest Russian leaders of all time — an equal to Peter the Great, or Joseph Stalin.

Putin is fast identifying himself with the greatest despot in Russian history

As an obsessive student of Russian history, Putin has had an evolving view of Joseph Stalin over the years. Early in his authoritarian rule Putin kept Stalin somewhat at arm’s length, both praising and criticising Stalin’s record. More recently, as Putin has transitioned from autocrat to dictator, he has moved further and faster to identify himself with the greatest despot in Russian history. Stalin statues are now appearing in different places around the country, and respect for Stalin as a historical figure has risen strongly across Russia.

In the last few weeks, Putin has put this trend into overdrive and started behaving in a manner that apes Stalin almost perfectly. As Stalin in 1939 decided to invade the Soviet Union’s neighbour Finland, so has Putin today invaded his neighbour Ukraine. In both cases the decision for war was made by the dictator talking to a very small group of cronies, and in both cases the mass of the Russian people seemed indifferent or even hostile. Also, both invasions were disasters that revealed massive shortcomings in the Russian armed forces. In Stalin’s case, however, he was allowed time to rectify the problems, and his regime survived. It’s not clear that this will be the case for Putin.

The public meeting where Putin both embarrassed the other leaders in the Russian state security hierarchy, and forced them to publicly associate themselves with his decision to invade, was pure Stalin — if Stalin were alive today and could do it on television. As his rule became more bloody and despotic, Stalin increasingly forced his inner circle to endorse in writing his worst depredations, from signing the execution warrants of those slated for destruction, to publicly speaking in favour of policies that would force millions to starve. It both served his interest to humiliate his inner circle by reinforcing that they had to do his bidding no matter how onerous, and at the same time gave the impression to the outside world that his policies were strongly supported by the ruling circle. Putin is evidently doing the same, which is why he was so withering to the head of Russian intelligence, Sergey Naryshkin, when the latter seemed to waffle on the policy of recognizing the Russia puppet regimes in Donetsk and Luhansk.

Many Russian soldiers froze to death in the deep Finnish forests, with no idea why

If this is a great scheme to emasculate those around him, it does present a problem for a dictator desperately in need of sound advice — which both Stalin was and Putin urgently is. By 1939, Stalin had created such an inert echo chamber of advisers, that when he suggested a dangerous move such as the invasion of Finland, he only received choruses of support.

The invasion revealed huge shortcomings in his strategic vision and the military force he had built up in concert with it. Stalin decided to move on Finland in 1939, based on the assumption that with the rest of Europe distracted by the great war that had just started between Nazi Germany and Britain and France, he could militarily overwhelm tiny Finland in a week or two and dictate whatever peace treaty he wanted. Indeed, he told himself, many Finns would welcome Red Army soldiers as liberators, and he might even take Finland back under direct political rule of Moscow, as it had existed under the Russian Empire. He amassed a large number of ill-prepared troops on the border and ordered them to attack on 30 November.

The results of this Winter War were a shock and a humiliation for Stalin. Red Army forces were stopped almost immediately by determined, well-planned Finnish defenders, fighting on land they knew well. Red Army soldiers were poorly led, had almost no useful information about the army they were attacking, and were often disorganised, leading them to be massacred in huge numbers during the opening weeks of the fighting. Many Russian soldiers froze to death in the deep Finnish forests, poorly equipped and with no idea why they were there.

It’s not clear that Putin will be allowed as much latitude as Stalin to recover

This has eerie parallels with what has happened during the Russian invasion of Ukraine. Putin clearly believed that this would be an easy campaign, with Kyiv seized in a few days and fighting lasting at most a few weeks. Moreover, he must have been convinced that the Ukrainian people would be accepting of his rule. It’s the only way to explain the half-assed and amateurish way the campaign started. Daytime airdrops at easily reinforceable airfields (which were quickly recaptured by the Ukrainians), an inability to assert control of the air against a relatively small Ukrainian Air Force, and basic supply problems which has led to Russian soldiers regularly abandoning some of the most advanced equipment in the Russian Army, all reveal the chaos. Moreover, many Russian soldiers admit to having no idea what they are doing in Ukraine, expressing their shock that instead of being viewed as friends, they have been met by a violent and determined resistance that sees them as invading oppressors. Except for the fact that they are not freezing to death in the forest, the parallels between the two operations are noticeable.

Here is where they might end: Stalin was able to recover from his initial disaster. Though there was a great deal of international sympathy for the Finns, there was little desire to come to their aid in the midst of the European war. Stalin was thus given time to recover, to build up a new, massive army and equip it with overwhelming artillery firepower. In March 1940, he launched this new force against the Finns, cracking their defensive lines and forcing them to sign a peace which he dictated. It’s worth noting, however, that Stalin had been so burned by the power of Finnish resistance that even though he took a large slice of Finnish territory, he allowed Finland to remain politically independent.

It’s not clear that Putin will be allowed as much latitude as Stalin to recover from the disaster he has unleashed. International economic sanctions, led by the USA and the EU, are far more crippling than anyone had predicted, and the Russian economy is teetering. It’s not clear that the money will be there to sustain advanced military operations over time, and from the strength of Ukrainian resistance, it looks like the only way to hold any part of Ukraine would be through long-term occupation. He finds himself in a much worse position than Stalin when things started going wrong with the Winter War in late 1939.

Putin might have chosen a better role model.