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Ukraine endgames 2.0: Can either side ‘win’ this war?

Russian mistakes, Ukrainian resilience and NATO support have narrowed the options for how the conflict might end.

Two of those scenarios — a complete Russian takeover of Ukraine and a division of the country in two, with a new border along the Dnieper River — are now off the table. Before the war, many predicted the Ukrainian resistance to transform into an underground insurgency against a Russian occupation. Instead, Ukraine’s military is intact and still fighting a conventional war.

The true nightmare scenario of three months ago — a direct Russia-NATO war — is still possible but looks less likely today. Given the difficulties they’ve had overcoming Ukraine, it’s hard to see what the Russians could accomplish by striking Poland, the Baltic states or any other country under NATO’s security umbrella. This is not to say that an errant missile strike or misread intelligence couldn’t still lead to a deadly miscalculation.

The other scenario in the March list — a negotiated settlement — seems a distant hope for now. Ceasefire talks between Ukraine and Russia have been on hold since revelations about the massacre of Ukrainian civilians in areas around Kyiv emerged in early April. A deal may eventually end this war — it’s arguably still the mostly likely outcome — but it doesn’t seem to be coming soon.

So how have the likely outcomes changed?

Where things stand

“We underestimated the Ukrainians and exaggerated the strength of the Russians. Now, I think we’re doing the reverse,” Thomas Graham, former Russia director of the White House National Security Council, told Grid. “Russia still has significant resources that they can throw into this conflict today.”

We know this much: The potential outcomes today are not what they appeared to be three months ago. So, with all necessary caveats and a great deal of humility, here’s an updated look at the most likely endgames for the war in Ukraine. All are long-term scenarios contingent on events on the battlefield. As Lawrence Freedman, emeritus professor of war studies at King’s College London, told Grid, “we’ll get a better idea later this month” of which scenario is most likely.

Russian victory

Kyiv may be off the table for now, but the more modest goal of taking all of Donetsk and Luhansk, the two Ukrainian provinces that make up the Donbas region, remains attainable. While progress has been slow, Russia has made gains in the Donbas. Russian forces also control the southern cities of Berdyansk and Kherson, meaning there is now a land bridge between Russian-held areas in the east and the Crimean Peninsula, which Russia annexed in 2014, cutting off Ukraine’s access to the Sea of Azov.

The final fall of Mariupol will free some Russian battalions for fighting elsewhere (though these units are not exactly in prewar condition), as will the Russian retreat from the area surrounding Kharkiv in the northeast. With these reinforcements and their advantages in firepower, the Russians could continue the slow grinding work of encircling Ukrainian forces in the Donbas, eventually forcing a retreat.

In political terms, Putin would declare that the people’s republics of Donetsk and Luhansk have been liberated from Ukrainian forces; he might even annex these areas into Russia. Russia might also either annex or support a new self-declared autonomous region in Kherson, or other areas it has taken over outside the Donbas.

Return to status quo

Politically, this would be a tough sell for both sides. There’s no “off-ramp” in this scenario for Putin: Russia will have lost thousands — perhaps tens of thousands — of lives and cratered its own economy to accomplish absolutely nothing. For Ukraine, after the horrors of Bucha, Chernihiv and Mariupol, there will be little appetite to stop fighting while Russia is still occupying parts of its territory.

For Ukraine’s Western backers, however, a return to the status quo ante that stops the killing, turns down the risk of World War III and begins the rebuilding of Ukraine is going to look a lot more appealing as the war — along with the refugee flows and billions of dollars in weapons shipments — drag on month after month. French President Emmanuel Macron is among a small group of leaders already searching very publicly for a way out.

Freedman told Grid that foreign leaders should avoid “defining Ukrainian objectives for them.” He continued: “if you look at the balance of forces, it’s not looking bad for Ukraine. The Russian morale is in decline. They’re having real problems, whereas Ukraine is getting stronger. I really don’t think it’s an impossibility that Ukraine could win.”

Full Russian collapse

A couple of breaks would have to go Ukraine’s way to make this happen. Kyiv’s Western backers would have to continue the flow of weapons, money and equipment for a long time, and the Russian state’s will to fight would have to collapse. We may get a better sense of whether this is possible in a few months, as Russian losses rise and international sanctions really start to bite into the Russian economy.

Forever war

What if the war just doesn’t end? After all, Ukraine and Russia had been in a state of low-intensity warfare from 2014 until 2022. Could that sort of violent stasis return?

Graham, now a fellow at the Council on Foreign Relations, told Grid he can envision a scenario in which Russia is able to “freeze the situation where they are, where they are in control of a substantial amount of Ukrainian territory, in the hopes that this would devolve into something similar to this situation to have had in the Donbas for the past eight years: a line of contact, periodic shelling across that line, people die on both sides, but no major military operations or significant exchanges of territory.”

Any pause likely wouldn’t last long. Cranny-Evans warns that if the Russians are able to rest and regroup, we could see “a return of Russia’s maximalist aims” — attacks beyond the Donbas aimed once again at regime change, this time with Ukraine’s most capable military units badly degraded.

This would be a stretch for Russia’s capabilities, and Ukraine has far more internationally supplied firepower at its disposal than it did when the war began, but as we consider “endgames,” it’s worth keeping in mind one grim fact: We probably haven’t yet come to this war’s final chapter.

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