The Crimea question: Why Ukraine’s final battle might be the Western alliance’s toughest test

Joshua Keating

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The official position of the Ukrainian government is clear: Its forces will continue fighting until they have recaptured all of Ukraine’s internationally recognized territory. That is, not just the areas Russian forces have captured since their February invasion, but all the territory they have occupied since 2014. This includes the Crimean Peninsula, which Moscow formally recognized as its own after staging a hasty and flawed referendum eight years ago.

In the early days of the war, a battle for Crimea seemed highly unlikely; the Ukrainians had enough to worry about simply halting the Russian advance. But now the Ukrainians are on the offensive. And now senior Ukrainian leaders are sounding optimistic about retaking the peninsula.

At the recent Halifax International Security Forum, former Ukrainian president Petro Poroshenko concluded his remarks by suggesting that next year’s edition of the annual security summit be held in “Yalta or Sevastopol,” two Crimean cities. Noting that Yalta was where Allied leaders met in 1945 for a key summit to plan the postwar international order, senior presidential adviser Mykhailo Podolyak recently proposed it as a site to try Russian war criminals. “What started in Crimea — must also end there,” he tweeted. “There is no other way to force kleptomaniacs to respect international law rather than in a trial where the modern UN was founded.”

Of course, before Ukraine can host international events in Crimea, it needs to recapture the peninsula. In a recent interview with Sky News, Deputy Defense Minister Volodymyr Havrylov suggested it was possible that Ukrainian troops would enter Crimea “by the end of December” and that the whole war might be over by spring. As of the beginning of December, that timeline looks extremely optimistic, but Ukrainian commanders have reportedly been working on plans for capturing the peninsula — plans that at least some outside observers who’ve been briefed say are credible.

For many Ukrainians, only the recapture of Crimea would bring a real end to the eight-year military conflict with Russia. Polls suggest a large majority consider it the only acceptable “victory” in this war. For Russians, the 2014 annexation righted a historical wrong done to them at the end of the Cold War, and the peninsula has taken on an almost mystical importance. Losing it now, in a war that was meant to gain territory, would be a monumental humiliation for the Kremlin. The political stakes of the battle couldn’t be higher.

The stakes are high for the U.S. and its European allies as well. Officially, the position in Washington and other Western capitals is that “Crimea is Ukraine” and that support for the Ukrainian war effort will continue for as long as it takes to end the Russian occupation. When speaking anonymously, however, Western officials are more likely to concede that Crimea may need to be treated a bit differently.

“The West has been a little more careful talking about Crimea compared to the rest of Ukraine,” said William Courtney, a former ambassador and White House Russia adviser now with the nonprofit Rand Corporation. “I think for two reasons: the military challenge and the risk of escalation.”

Earlier this month, Gen. Mark Milley, chairman of the U.S. Joint Chiefs of Staff, came closest among senior Western officials to publicly acknowledging these misgivings when he said, “The probability of a Ukrainian military victory — defined as kicking the Russians out of all of Ukraine to include what they claim as Crimea — the probability of that happening any time soon is not high, militarily.” He suggested that Ukraine’s recent military momentum made this an auspicious time to negotiate a political solution to the conflict. Reading between the lines, this would almost certainly be a solution that left Crimea in Russian hands.

So far this year, Ukraine has repeatedly surprised the world with the effectiveness of its military campaign, and its Western allies have surprised with the steadfastness and unanimity of support for that campaign. For all the doubts expressed earlier in the war, there’s been little daylight between the messages from Kyiv and from its Western supporters. Looking ahead, the question of Crimea may pose the biggest challenge to that partnership.

A tough fight ahead

It’s difficult to know exactly what sort of resistance the Ukrainians will meet in Crimea given that troop numbers have fluctuated significantly since the start of the war and that the battle — Havrylov’s optimism notwithstanding — is likely some ways off. But we do know that the peninsula, which includes the historic home of Russia’s Black Sea fleet at Sevastopol, is heavily militarized. More than 31,000 Russian troops were based there even before the massive troop buildup that preceded this year’s invasion. The peninsula’s defenses may soon be bolstered by new troops from Russia’s recent mobilization. These might not constitute the most well-prepared, equipped or trained fighting force, but they are bodies to put on the line for a military that is comfortable with a high number of casualties.

Unlike the September offensive in the eastern Kharkiv region, where Ukrainian forces broke through thinly manned and ill-supplied Russian lines, the closer the Ukrainians get to Crimea, the better-defended the Russian positions will be. The offensive is likely to look more like the slow grinding approach to Kherson, during which the Ukrainians took heavy casualties for months, in exchange for relatively small territorial gains.

“[The Ukrainians] chewed themselves up pretty badly fighting for Kherson,” Chris Dougherty, a former Pentagon wargamer who is now a senior fellow at the Center for a New American Security, told Grid. “I know we were all kind of intoxicated by the seizure of Kharkiv and the surrounding region. But everything since then has been a lot more difficult and a lot more casualty-intensive on the Ukrainian side.”

Of course, the Russians withdrew from the city of Kherson, to the surprise of many who had expected a protracted fight for the provincial capital that the Russians had taken with great fanfare in the early days of the war, but Dougherty said this shouldn’t lull anyone into a false sense of confidence. By withdrawing from the city to the portion of Kherson Oblast between the Dnieper River and Crimea, the Russians have established a much easier position to defend. “The withdrawal from Kherson was politically humiliating but militarily the right choice, which is not something the Russians have done a lot of in this war,” Dougherty noted.

Treacherous ground

The geography doesn’t help the Ukrainian cause. Given that Ukraine is not thought to have much in the way of amphibious landing capabilities, that means any assault on Crimea would involve a ground invasion. Much of the land between the Ukrainian mainland and Crimea is an area of swampy lagoons known as the Svyash, or Rotten Sea, with relatively narrow land approaches depending on the tides.

Alina Frolova, a former Ukrainian deputy defense minister, told Grid that while she anticipates Crimea will be a realistic target for Ukrainian forces after they push the Russians out of eastern Kherson, these on-the-ground realities will make any advance very difficult. “Obviously the problem is with access to Crimea,” she told Grid. “We have very narrow access, and that’s obviously not the best position with high force rates.”

Adding to the difficulties are the coming winter cold, which is already slowing down offensive operations everywhere in Ukraine, as well as the spring thaw that will follow and turn terrain in some areas into impassable mud.

Frolova, now with the Kyiv-based Center for Defence Strategies, also noted that while the October explosion on the Kerch Bridge connecting Crimea to Russia hurt the Russian ability to resupply its forces there, the bridge is still partly operational and Russian forces in Crimea are better supplied than their counterparts in much of eastern Ukraine.

She anticipated that Russia’s naval forces in Crimea would need to be “dramatically decreased” before a major offensive could begin. Otherwise, she said, “we will face quite substantial capabilities.”

In a sign that this effort to degrade Russian strength may have begun, authorities in Sevastopol last week reported another drone attack on the port city, following a series of similar attacks over the summer. The Ukrainians have also been pushing the U.S. to supply them with longer-range missiles like the ATACMS, which can be mounted on their highly effective HIMARS launchers and would make it easier to strike targets within Crimea from Ukraine.

Tricky politics

Ukraine’s challenges when it comes to Crimea aren’t just the military variety. While there are certainly pockets of pro-Russian sentiment in mainland Ukraine, it’s likely far higher in Crimea. The region has always had a higher proportion of ethnic Russians than the rest of Ukraine, and as observers often point out — including most prominently Elon Musk in his now infamous “peace plan” tweet — it became part of Ukraine only when it was transferred from Russia by Soviet Premier Nikita Khrushchev in 1954, at a time when both were part of the Soviet Union.

None of this makes Russia’s annexation of the territory legal or legitimate under international law. As Ukrainians often point out, a majority of Crimeans — albeit a very slim majority — voted for independence in 1991 along with the rest of Ukraine, and Moscow agreed to respect newly independent Ukraine’s borders.

Frolova has little patience for the argument that Crimea has historical links to Russia. “Many regions have historical links with other countries, not only in Ukraine,” she said, pointing out Trieste, an Italian city that was historically part of the Austro-Hungarian Empire, as an example. “That doesn’t mean Germany or Austria have rights to it. Crimea also has historical links with Turkey. I don’t understand how this argument can be used seriously in political life.”

Legitimate or not, it’s still likely that Crimea’s population is more “Russian” today than it was in 2014. According to Russian statistics, around 150,000 presumably pro-Ukrainian residents left the peninsula for other Ukrainian areas in the three years after 2014. Roughly the same number of people moved from Russia to the region, encouraged by government incentives.

“When we’re talking about the people living in Crimea, that’s absolutely different than what we had eight years ago,” Ukrainian Deputy Prime Minister Olha Stefanishyna told Grid during a reporter’s roundtable at the Halifax forum.

Add to this the fact that residents have been under de facto Russian rule and consuming Russian media for the past eight years, and it’s reasonable to ask whether a Ukrainian recapture of Crimea would be greeted with the same scenes of public jubilation that have broken out in other liberated Ukrainian cities.

Still, Stefanishyna said she was “sure that our path toward the European Union and our successes on the battlefield will play a game-changing role in the transformation of thinking in Crimea. I think that Crimea will soon be back to Ukraine.”

Will the West support an offensive?

So far, despite some tense moments, the U.S.-led Western alliance has been able to pursue its sometimes contradictory goals in Ukraine: giving the Ukrainians what they need to counter the Russian invasion and avoiding an all-out war between nuclear-armed superpowers. Crimea, some suggest, could change that.

Russian President Vladimir Putin’s annexation of Crimea — a territory Russians long viewed as unjustly severed by the collapse of the Soviet Union — was enormously popular with the Russian public. Because of the territory’s role in the birthplace of Russian Orthodox Christianity, Putin has even referred to it as “holy land.” Russians may view Ukraine as a whole as “spiritually” part of Russia, to put it in Putinesque terms, but they view Crimea as literally part of Russia. Losing it would be a far greater political blow than any of the captured territory Russia has abandoned so far in this war.

“I think the discussion of acceptable risks and escalation risks would become much more acute if it actually looks like the Ukrainians were positioning to actually take back Crimea,” Jeffrey Edmonds, a former Russia director for the U.S. National Security Council now with the Center for Naval Analyses, told Grid.

For obvious reasons, the question of whether Putin would order the use of a nuclear weapon to prevent the loss of Crimea has gotten the most attention, but Edmonds noted, “There are many capabilities the Russian military has that it has not used in this conflict: undersea capabilities, anti-space capabilities. There’s a whole toolbox of things they have that could raise the stakes.”

Beyond these risks, a Ukrainian campaign to retake Crimea would no doubt extend the war. With growing questions over the West’s political will as well as its physical stocks of ammunition and other supplies, it’s possible policymakers in some capitals will wonder if it’s worth continuing to fight to retake an area they weren’t willing to fight for in 2014.

The most painful bargaining chip

In making the case to supporters for why Crimea may be worth the fight, Ukrainian officials have increasingly referred to international law and the U.N. Charter, which enshrines the inviolability of territorial integrity. The argument goes like this: Recognizing Russian control of Crimea would legitimize the kind of forceful land grabs that have been mercifully rare in the post-World War II era.

Then again, wars often end with messy and unsatisfactory compromises. To take one timely example: This week marks the anniversary of the Soviet Union’s 1939 invasion of Finland, a conflict during which the Finns showed surprising resilience and embarrassed the much larger Soviet military but were eventually ground down by superior numbers and ceded 10 percent of their territory. Even as they insist full liberation of Ukrainian territory — including Crimea — is possible, Ukrainian officials often concede that painful compromises may be necessary.

In any event, international recognition of Crimea as Russian territory remains highly unlikely. Courtney, the former ambassador, suggested a more likely scenario would be something like the Baltic countries during the Cold War: From the time the countries were occupied by the Soviet Union in 1940 until they achieved de facto independence in 1991, the U.S. continued to officially recognize them as independent states. Crimea would remain an anomaly and a kind of geopolitical black hole.

For now, Ukraine has the battlefield momentum, and as long as it can maintain that momentum, Western governments are likely to continue publicly backing Kyiv, whatever their private misgivings. The fact that Crimea’s status is even a matter for discussion is a testament to how surprisingly effective the Ukrainian resistance and counteroffensives have been. The arguments between Ukraine and the West will come if and when the Ukrainians feel ready to make their move.