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

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

One week after the war in Ukraine began, Grid laid out five scenarios for how it might end. It was already apparent then that the war would not be the quick and decisive Russian rout that many had expected, but two months later, it’s clear that the article still gave the Russian military too much credit.

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.

A palace coup in the Kremlin — another scenario from the article — remains a possibility, and a cottage industry of speculation about the state of Vladimir Putin’s health has emerged, but so far, there have been few signs of cracks within the Russian president’s inner circle. While there have been some scattered moments of high-level dissent, we haven’t yet seen the kind of fracturing among Putin’s top aides or mass public opposition that would force the Kremlin to change its strategy. Anything is possible, but it’s probably not a good idea to count on a deus ex machina emerging in Moscow to bring the killing to a close.

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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.

One scenario that notably did not make Grid’s initial list was an outright Russian defeat. Today, an increasing number of Western lawmakers and prominent commentators say that Ukrainian victory is the only acceptable outcome and that international support must continue until it is achieved. “Victory” for Ukraine is no longer inconceivable after the Russian retreats from Kyiv and the country’s second-largest city, Kharkiv, though those calling for victory often don’t define what exactly it would mean.

So how have the likely outcomes changed?

Where things stand

The current state of play is that Russia and Ukraine are locked in a brutal and artillery-heavy war of attrition in the Donbas region in the east. Russian forces have failed at their initial goals of capturing all of Ukraine and are having difficulty with even the more limited goals they’ve been pursuing since April. Ukrainian forces have mounted successful counterattacks and forced Russian troops to withdraw from the city of Kharkiv but haven’t been able to disrupt Russian supply lines, and the Ukrainian troops in the besieged city of Mariupol surrendered this week. The situation is approaching a stalemate, though not yet to the point that either side is ready to negotiate concessions.

“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.”

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While Russian forces have been losing troops and equipment at a prodigious rate, they seem to have no shortage of artillery systems and ammunition — which could prove decisive in this next phase of the war. And there’s been comparatively little coverage of Ukrainian casualties compared with Russian losses; Ukrainian forces may be in worse shape than we think. But they clearly have advantages in morale, cohesion and international support.

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.

This might just be enough for Putin to declare victory in his “special military operation.” But Russian forces’ battlefield performance is going to have to improve dramatically to allow him to do so, and it may only be a matter of weeks until personnel losses make even this smaller-scale “victory” impossible.

Return to status quo

Russia’s quick and bloodless annexation of Crimea in 2014 was an exception to the rule. Generally speaking, in recent decades, most attempts at territorial conquest have failed, and the most common outcome — think Iraq and Kuwait in the 1990s, Argentina and the Falklands in the 1980s, or North and South Korea in the 1950s — has been a restoration of the borders that existed before the invasion. In the Ukraine case, this would mean Russian forces retreating to the areas of Ukraine they controlled as of Feb. 23: Crimea, and parts of Donetsk and Luhansk.

Ukrainian counteroffensives have already forced Russian forces to withdraw from Kyiv and Kharkiv. Another counteroffensive was recently launched on the Russian-held town of Izyum, a key supply node in Russia’s efforts to encircle Ukrainian forces in the Donbas. Still, says Sam Cranny-Evans, a research analyst at the Royal United Services Institute in London, to achieve a return to the pre-February borders, “Ukrainians have to be able to not just withstand what the Russians are currently doing, but actually push it back as well. And I think that may be quite a big ask.”

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.


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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

Officially, at least, when Ukraine says it wants Russian forces out of its territory, it means all of its territory. Foreign Minister Dmytro Kuleba recently told the Financial Times that while the original Ukrainian goal had been to force Russian forces back to their pre-Feb. 24 positions, battlefield success had caused his government to upgrade its goals, and that “victory for us in this war will be the liberation of the rest of our territories.”

As Kuleba himself acknowledged, this will be tough. The general rule of thumb in warfare, which Russia has been reminded of the hard way, is that in a fight over territory, the defender holds a 3-to-1 advantage over the attacker. If Ukraine attacks Russian-held areas of the Donbas, that advantage will flip to the Russians. After months of bruising battle, the Ukrainians will be moving against heavily fortified Russian positions with stretched supply lines. Taking Crimea seems very unlikely: It’s a well-fortified peninsula, the Ukrainians may face a hostile civilian population, and given that Moscow considers it Russian territory rather than just a Russian-backed separatist region, an attack on Crimea is arguably the sort of threat to the “very existence” of the state that would justify nuclear weapons use under Russia’s official doctrine.

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?

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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.”

Russia likely does not have the ability to continue fighting at the current level of intensity deep into this summer. Some sort of operational pause will be required, at which point it may push for a ceasefire deal. The Ukrainians are likely to be skeptical of any deal that gives Russia time to replenish its reserves, but depending on the state of its own forces, Kyiv may have to agree. As Kuleba acknowledged in the same Financial Times interview, Ukraine may be forced to eventually negotiate a settlement but wants to “approach the unavoidable moment with the strongest cards possible.”

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.

Thanks to Lillian Barkley for copy editing this article.

  • Joshua Keating
    Joshua Keating

    Global Security Reporter

    Joshua Keating is a global security reporter for Grid focused on conflict, diplomacy and foreign policy.

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Ukraine