Wars are complicated matters, and whatever one thinks of Donald Trump’s strategy in Iran, one thing is certain; he is not going to make Putin-style mistakes. History has shown us repeatedly that while one nation can conquer and occupy another nation’s land, it is far more difficult to conquer the people who live on it.

And that’s precisely the situation Trump wants to avoid in Iran.

Meanwhile, with Putin’s handling of the Ukraine situation, the die is cast.  Before he invaded, Russia retained considerable cultural, political and economic influence among Ukrainians. But after more than four years of carnage, an entire generation of Ukrainians now includes opposition to Russia in general, and Putin in particular, as part of its national identity.

There are sound historical arguments on both sides of the Russia-Ukraine question.  The two countries share centuries of history, religion, culture and political association.  However, Russia has a particularly keen strategic interest in what happens along its borders and views potential NATO expansion into the area as threatening and a significant part of the overall equation.

Putin expected the Ukrainian government to collapse shortly after he invaded. Instead, the invasion strengthened Ukrainian national identity, increased Ukrainian hostility toward Russia, brought Finland and Sweden into NATO and precipitated increased defense spending across Western Europe – exactly the opposite of what Putin presumably wanted in the first place.

~ Putin’s Problems ~

Putin has invested enormous amounts of Russian blood, money and prestige into the Ukraine War and occupies roughly 20% of the country.  Meanwhile, Moscow insists that negotiations recognize the “realities on the ground.”

But that creates a different problem.  The lives already lost cannot be recovered regardless of what Putin does moving forward.  And from a purely rational standpoint the question should be: From this day forward, will another year of fighting produce benefits worth another year of lost blood and treasure?

Unfortunately, authoritarian rulers don’t necessarily think that way.

Putin would still have to explain why Russia endured years of casualties, sanctions and economic disruption if the eventual settlement looks substantially like something he might have obtained without invading.  But he has an even deeper problem: Putin sees himself as an historic figure and cannot easily admit that his original calculation was wrong – and that may be the single biggest stumbling block to ending the war.  Losing Ukraine permanently to the Western political and economic orbit would represent an historic Russian defeat, leaving an indelible stain on Putin’s legacy.

Meanwhile, there’s a hidden irony in the matter.  Even if Putin finishes the war controlling substantially more Ukrainian territory than Russia possessed in 2022, by acquiring its territory he will have lost the very people he claimed were inseparable from Russia.

Consequently, Putin’s calculation today may be less about conquering Ukraine than finding an outcome that preserves Russia’s status as a great power, avoids an obvious strategic defeat, validates the enormous sacrifices already made, and protects his authority and historical legacy. But that’s a tall order. The world has had a front-row seat watching the once-vaunted Russian military devolve from a force widely feared into one whose limitations have been exposed for all to see.

Zelenskyy faces a different situation.  His objective is to end the fighting, preserve an independent Ukraine, obtain Western security guarantees to deter another Russian invasion in the future and leave the territorial questions for another day.

However, Putin and Zelensky do have one thing in common: public perception. If Putin simply withdraws, he’ll have to explain to the Russian people what four and a half years of war and enormous sacrifice accomplished. Conversely, if Zelensky simply hands Russia the territory it has seized, he’ll have to explain to Ukrainians why they endured four and a half years of death and destruction only to surrender much of what they fought to defend.

But anything is possible.  Korea has demonstrated for more than 70 years that warring factions can stop the shooting, establish a defensible line, provide credible security guarantees and postpone the question of ultimate sovereignty—an endgame that strikes me as considerably more achievable than expecting either Putin or Zelenskyy to formally concede everything the other side demands.

Whatever the eventual agreement, there’s one consequence of Putin’s invasion that he cannot undo.  Millions of Ukrainians have endured years of death, displacement and destruction. Borders can eventually be negotiated and territory can change hands, but the enmity Putin has created will remain.

So, while Putin may ultimately gain Ukrainian territory, he has almost certainly lost Ukraine.  And that may prove to be his greatest strategic miscalculation and the most enduring part of his legacy.  Lastly, I’ll bookend this post by stating with a good degree of confidence that you can be sure, Donald Trump will not repeat Putin’s mistake.