Putin's Desperation Moves: Symbolic Strikes on Kyiv and the Latvia Gambit

Vladimir Putin is on the ropes. On the battlefields of eastern Ukraine, Kyiv has built an overwhelming short-term advantage in drone warfare, sowing chaos across the Russian back lines and severing the land bridge between Crimea and the Russian border. On the home front, Ukrainian long-range drones are striking Russian refineries, factories, and even well-defended cities at such unprecedented rates that the Kremlin is now encouraging Russian banks and businesses to buy their own private air defenses. New and deadly weapons are swelling the Ukrainian arsenal, from Swedish Gripen fighter jets to American-made Hornet drones, as some ninety billion euros are about to flow into Ukrainian coffers.

The mood inside Ukraine’s senior command reflects that momentum. In a recent interview with Reuters, the commander of Ukraine’s Third Army Corps and founder of the elite Azov Battalion laid out his nation’s case bluntly: “I believe the next six to nine months are a turning point. More precisely, I think the next six are the most critical.”

But here is the warning we have issued before and will issue again: when Vladimir Putin gets desperate, that is when he is at his most dangerous. It is not clear exactly how many of Russia’s problems are actually explained to the nation’s leader, but if the reports leaking out of Russia are accurate, then Putin is paranoid, isolated, and aware of enough to know that he has good reason to worry about the future. Russia’s standard playbook is not working—and if his past conduct is any guide, he will not admit defeat. Instead, he will reach deep into the Kremlin playbook for a pair of highly unorthodox, high-risk options that could turn the entire status quo upside down.

Key Takeaways

Ukraine has gained an overwhelming short-term advantage in drone warfare, severing the Crimea land bridge and striking Russian refineries and cities deep inside Russia at unprecedented rates.
A cornered Putin is weighing two desperation moves: a focused decapitation campaign against Kyiv’s symbolic and leadership targets, and a probing attack on Latvia designed to fracture NATO over Article 5.
Both gambits are unlikely to succeed: Ukraine’s leadership operates from fortified bunkers and decentralized command centers, while European intelligence has anticipated the Latvia threat and NATO is racing to close the window.
Germany and the Netherlands are taking joint command of NATO land forces in Estonia and Latvia within months, and NATO will assign an entire corps — potentially 40,000 to 60,000 wartime troops — to the region.
A losing Putin is a more dangerous Putin: if neither gambit works, the ultimate trajectory of the war is unchanged, but far more blood will have been spilled to reach the same outcome.

A Cornered Kremlin

The strategic picture facing Moscow in late May 2026 is grim by almost any measure. Ukrainian drones dominate the contested ground in the east, paralyzing Russian logistics and cutting the overland connection between Crimea and Russia proper. Deep strikes reach industrial and energy targets far behind the front, with enough frequency that the Kremlin has resorted to telling private institutions to fund their own air defense. Western support, far from collapsing, is intensifying: Gripen fighters, Hornet drones, and a wave of roughly ninety billion euros are inbound.

Against that backdrop, the assessment from Ukraine’s own commanders—that the next six months are the most critical of the war—reads less like wishful thinking and more like an operational forecast. The trajectory favors Kyiv.

Yet none of this guarantees safety. The central premise of this analysis is that a losing Putin is a more dangerous Putin. Reports describe a leader who is isolated and paranoid, possibly insulated from the full truth of his situation but aware enough to fear it. A man in that position, with a playbook that has stopped working, does not concede. He gambles. And two gambles in particular sit on the table.

The Symbolic Blow

It is time for foreign diplomats to evacuate Kyiv. Or so said Sergei Lavrov, Russia’s long-time Foreign Minister and a close ally of Putin himself. Addressing the world in late May, Lavrov implored foreign nationals, ambassadors, and diplomatic staff to leave the Ukrainian capital as soon as possible, then dialed his American counterpart Marco Rubio to relay essentially the same message. Ukrainian citizens, Lavrov added, should stay away from the capital’s administrative buildings, military sites, and other sensitive targets ahead of a crippling wave of Russian strikes against, in his words, “decision-making centres and command posts.”

The warning did not come from nowhere. Just days earlier, Russia had carried out one of its largest attacks on Ukraine to date—an assault that included the use of a dummy copy of Moscow’s nuclear-capable Oreshnik ballistic missile, a piece of theater calibrated to maximize dread.

But Lavrov’s threat did not inspire the fear he was counting on. European leaders made clear they had no intention of recalling their ambassadors, and even the United States proved noncompliant, despite President Donald Trump’s relative receptiveness to Russian grandstanding. As of this writing, Lavrov’s big, bad attack has not happened—though close observers of the war note early signs that Russia really could be preparing comprehensive strikes against Kyiv. Either way, the message is unmistakable: between Lavrov’s threats and a recent run of similar warnings, Moscow is openly considering a substantial escalation of its long-range strike campaign, aimed squarely at Ukraine’s symbolic and leadership targets—from the Verkhovna Rada, Ukraine’s parliament, to President Volodymyr Zelenskyy himself.

Why Russia Has Mostly Spared Kyiv’s Symbols

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Watch the full video analysis on the WarFronts YouTube channel, presented by Simon Whistler.

After more than four years of full-scale war, it is genuinely strange that Russia has not been pummeling Kyiv with decapitation strikes. Moscow is trying to conquer Ukraine by any means necessary and has shown itself entirely willing to target Ukrainian leadership—including in the earliest days of the invasion, when Zelenskyy was hunted for assassination by large units of the mercenary Wagner Group and the Chechen Kadyrovites. Ukraine’s presidential and parliamentary buildings, its courts, and its ministry headquarters are all known, fixed targets. Given the atrocities Russian forces routinely commit, sparing high-profile sites in Kyiv would be a bizarre line for Moscow to draw.

And yet, apart from isolated incidents, Russia’s High Command has largely avoided those symbolic targets—partly because it has not seemed to try very hard to hit them. The reason ties back to a story Russia tells its own people. As strange as it sounds outside the propaganda bubble, Moscow frequently promotes the idea that it has exercised restraint throughout the invasion.

The justification shifts by the day. Sometimes Russia says it does not want to provoke escalation from NATO. Sometimes it claims it would never wage the kind of barbaric war NATO would. And sometimes it insists it is only conducting a “special military operation,” whereas such strikes would belong to a full-scale war it has not formally declared.

Restraint as Liability: The Hardliner Case for Escalation

As the war has dragged on and reports of imminent Russian victory have lost credibility, that posture of restraint has become a target of fierce internal criticism. According to the critics, Moscow’s supposedly puny enemy has held out this long only because Russia refuses to do what is necessary—because Ukrainians have not been properly reminded to fear Russian military might. The implied solution: demonstrate Russia’s willingness to carry out such strikes, and Ukraine will supposedly raise the white flag, making whatever concessions it can to avoid further destruction.

From Putin’s vantage point, looking for any way to turn the tide, symbolic strikes are tempting. They could stir support on the home front and reclaim the nationalist fervor of the war’s earlier years. They might drive a new wave of Russian volunteers, or sow paralysis in Ukraine’s chain of command that lets existing units press forward.

There are anticipated morale effects too—Ukrainian troops at the front forced to watch their capital burn, reminded that they are fighting an inevitable war against a great global power. And there is the possibility that the milbloggers and hardliners are right: that if Ukraine were shown the full scope of Russian capability, Kyiv and its Western allies would conclude it was past time to back down.

Why the Symbolic Blow Probably Fails

The trouble with this gambit is the same flaw that runs through every desperation move on the list: it is unlikely to work.

Historically, Russia—and Putin especially—has had a reliably good read on the threats that make Europe back down. Lately, that calculus has broken down. Overt displays of Russian military might have become far less credible, and Europe seems to know it. Nor is it even accurate to say Russia has been avoiding these targets.

In the wave of strikes on May 24, impacts did damage the Verkhovna Rada and caused significantly greater damage at the Kyiv Opera, the National Academy of Music, and the National Art Museum. Kyiv, Washington, and Brussels all saw those impacts—and none felt moved to change course when Lavrov threatened to go further. Russia can bomb an opera house. It changes nothing.

Just as important, such strikes would do little to alter the front, where Ukrainian drones hold a clear advantage regardless of what happens back in Kyiv. Worse for Moscow, it is not even clear Russia has the capability to hit what it wants. Even against fixed, open structures like the Verkhovna Rada, Russian projectiles struggle to break through Ukrainian air defenses, making real progress only when Russia launches a thousand or more projectiles nationwide at once—a feat it can manage only intermittently given the preparation and resource cost.

A Leadership That Cannot Be Killed

Ukraine’s actual leadership structure compounds the problem. It works mostly out of fortified underground bunkers, hidden meeting spots, and decentralized command centers scattered across the country. Zelenskyy and his inner circle have been so hard to kill not because Russia has not tried, but because they move constantly, protect their communications, and reveal a location only after they have already left it.

So Russia can attempt a massive attack on Kyiv—but if it cannot destroy any meaningful element of Ukraine’s leadership, or worse, cannot even hit the static targets in its crosshairs, Ukraine emerges from the affair looking stronger, not weaker.

There is one more reality that might stay Putin’s hand: by attacking symbolic and leadership targets, Russia implicitly grants Ukraine permission to do the same in return. Ukrainian drones can strike deep into Russian territory; Ukrainian intelligence can track and kill Russian commanders regularly. At this phase of the war, who is to say Ukraine is not the one holding back?

That argument is more credible for Kyiv than for Moscow—Ukraine was denied long-range strike weapons for years precisely because its NATO friends feared deep strikes into Russia would escalate things. Kyiv can deduce what might follow if it killed a Russian minister, launched a drone barrage at the Kremlin, or took out Putin himself. But if Russia sets the precedent first, Ukraine might declare open season.

The Lateral Expansion

Beyond a more focused air campaign against Kyiv lies a second, more alarming possibility: a lateral expansion of the war through a strike against a vulnerable NATO nation—probably Latvia. This is a scenario the WarFronts team explored in detail with Illya Sekirin, a strategic advisor to Ukrainian High Command, in an interview published a couple of weeks earlier. The response in the comments at the time was predictable: even if Russia had the army to do it, there is absolutely no way Putin would do something that stupid.

A few weeks later, the picture has changed. Since that interview, several major outlets have confirmed that European intelligence is now deeply concerned about a Russian probing attack on a NATO member—and they agree Latvia is probably in the crosshairs. On Friday, May 29, Swedish defense chief Michael Claesson told Politico that a Russian threat to the Baltic states “could happen anytime.”

Russia, for its part, has been building its case against Latvia. On May 19, Russia’s ambassador to the United Nations warned: “the coordinates of decision-making centers in Latvia are well known, and membership in NATO will not protect you from retaliation.” Specifically, Russia has alleged that Ukraine planned to launch military drones from Latvian soil and that of the other Baltic states—though Latvia in particular seems to have drawn Moscow’s ire.

Why Latvia Looks Like the Perfect Target

Several factors make Latvia an unusually attractive candidate for a Russian provocation. Over recent weeks, Latvia’s government collapsed and was replaced amid a scandal in which Latvian air defenses failed to deal with two stray Ukrainian drones that veered off course and struck an empty oil storage site—an embarrassing demonstration of vulnerability. In Moscow, meanwhile, the Russian State Duma approved a law allowing Russia to use military force to protect Russians abroad, deploying soldiers in defense of those who face “arrest, imprisonment, or trial overseas, including in international courts.”

That law dovetails ominously with Latvia’s demographics. Nearly one-quarter of Latvia’s population is ethnic Russian, mostly living near the Russian and Belarusian border, and up to thirty-five percent of Latvians speak Russian as a first or primary home language. Russia would not lack a pretext.

Then there is the broader pattern of incursions. Friday, May 29 also saw the latest incident in which Russian drones entered NATO-member territory—this time Romania, where a drone crashed into an apartment building in what appeared to be an interception attempt gone wrong. The airspace around the alliance’s eastern edge is already being tested.

The Logic of Fracturing the Alliance

It may still seem ludicrous that Russia would attack a NATO member. But escalatory brinkmanship is exactly how Putin has approached the alliance for decades—and usually he gets NATO to back down. The logic here is straightforward: by challenging NATO directly, Russia stands a chance of forcing the alliance to fracture and to renege on its collective-defense obligations at the moment of truth.

The cracks are visible. Western European nations like Spain have shown how unwilling they are to remilitarize. Capitals like London and Paris struggle to keep pace with more war-ready eastern countries like Poland and Finland. And under the Trump administration, it is entirely possible that America could simply decline to come to NATO’s defense, citing European spending failures, recent diplomatic disputes, or whatever else the White House might choose.

If Putin can fracture the alliance, he can fracture the very foundation Ukraine stands on. Aid stops flowing, support dries up, and maybe—just maybe—Kyiv collapses under its own weight.

Crucially, Putin would not need to conquer the entire Baltic region to achieve this. It is a failure of understanding to assume he would have to overrun Latvia and Estonia, break through the Suwalki Gap in Lithuania, and bring three NATO members to heel at once. He almost certainly lacks the resources for that. But he does not need them. A NATO crisis requires only a limited, probing offensive—localized to an area with a friendly population, weak local defenses, and minimal strategic value to the alliance.

The Article 5 Trap

That is precisely why Latvia sits in the crosshairs. It has an eastern corner populated largely by Russian-speakers, where NATO defenses are underwhelming at best, and where Russia can cut in from its own territory and from Belarus with as few as a couple of thousand troops—parking themselves on that ground and daring NATO to respond.

For the alliance in its current state, that is the worst-case scenario: an invasion engineered to create a make-or-break situation on Article 5, where NATO is absolutely obligated to defend itself collectively, but where the target is not actually important and might even be Russia-friendly. In that situation, it becomes all too easy for French or Italian leaders to insist their troops will not die over a tiny patch of Latvian soil, or for Donald Trump to accept Putin’s claim that Russia is merely defending Russian-speakers on foreign ground.

It is a trap built not around territory but around political will—an attempt to make the alliance’s central promise look not worth keeping.

Why the Latvia Gambit Is Closing Fast

There are two very serious problems with this approach if Russia actually tries it.

The first is timing. This kind of attack might have worked on the NATO of two years ago, or even a year ago. But the alliance has likely come just far enough to handle it.

European leaders have been preparing for a coalition deployment into Ukraine outside the NATO framework and without US leadership for some time. The continent is drawing up plans to manage its own defense rather than rely on Washington if it comes to that. Countries on or near NATO’s eastern front—especially Finland, Poland, and Germany—are demonstrating they will respond to Russian aggression regardless of an alliance-wide decision, and NATO itself is learning to become more flexible, letting those countries take the lead on rapid response without turning the moment into the referendum on NATO unity that Putin wants.

The second problem is that the element of surprise has evaporated—Europe knows an attack on Latvia might be coming. On May 28, the governments of Germany and the Netherlands announced they will take joint command of NATO land forces in Estonia and Latvia within just the next couple of months. That means Berlin and The Hague—not Washington—will make the split-second tactical decisions to defend the Baltics, and it puts NATO commanders much closer to the front, allowing them to draw in what one NATO official described to Reuters as “mass at speed.”

A Corps on the Way, and Russia’s Other Options

Even more significant was an announcement two days earlier: NATO will assign an entire corps to Estonia and Latvia, on top of the new tactical command. In wartime, an army corps comprises several divisions—potentially forty to sixty thousand troops. Even a peacetime deployment, though smaller, is expected to bring new air defense, artillery, and other key capabilities that will double NATO’s existing defenses there.

And all of it is expected on a timeline of just a couple of months. By the time Russia can divert and build up enough force to slice off a piece of Latvian territory, it may already be too late to get away with it.

Latvia is not Russia’s only option for lateral expansion. NATO sources note that Russia could try to seize a bit of high-Arctic territory from Finland or Norway, or occupy a vulnerable island like Gotland or Svalbard. Alternatively, as a separate WarFronts episode explained, Russia could attack a more isolated, non-NATO country to make an example of it—rallying the home front and trying to instill fear in Ukraine and its allies.

That episode spotlighted Georgia, where a Russia-friendly government could essentially roll over for an easy conquest or intervention, and Armenia, a tiny country that even a relatively small Russian offensive could overwhelm. But both European intelligence and the thrust of Russia’s public statements point to Latvia as the country in Russia’s sights—and Russia’s window appears to be closing fast.

The Roads That Lead to Ruin

With luck, the world will not have to confront either of these desperate attempts to change the status quo. Perhaps, for once, Putin and his close advisors will see reason, or develop an understanding of their strategic situation that more closely matches the world around them.

If Russia does decide to escalate, both options examined here will probably lead to ruin. But if Putin understands what is happening in Ukraine, then he already understands that this war is leading to ruin anyway. Should one last, desperate gambit fail, the ultimate outcome of the war is unchanged. It is only that far more blood will have been spilled to reach it.

Presented by

Simon Whistler

Simon Whistler is one of YouTube's most prolific educational creators. WarFronts is his deep dive into military history and conflict analysis.

Frequently Asked Questions

What are the two “desperation moves” Putin is weighing?

The first is a focused escalation of long-range strikes against Kyiv’s symbolic and leadership targets, such as the Verkhovna Rada and President Zelenskyy. The second is a lateral expansion of the war through a probing attack on a vulnerable NATO state — most likely Latvia — designed to fracture the alliance by creating a make-or-break test of Article 5 on low-value, Russia-friendly terrain.

What did Sergei Lavrov demand, and how did the world respond?

Lavrov urged foreign diplomats and ambassadors to evacuate Kyiv ahead of strikes on “decision-making centres and command posts,” and relayed the same message to US Secretary of State Marco Rubio. European leaders refused to recall their ambassadors, and even the United States did not comply. As of writing, the threatened attack had not occurred, though observers note early signs Russia could be genuinely preparing strikes.

Why would symbolic strikes on Kyiv probably fail?

Ukraine’s leadership operates from fortified underground bunkers, hidden meeting spots, and decentralized command centers. Zelenskyy and his inner circle move constantly and reveal locations only after departing. Even against fixed structures like the Verkhovna Rada, Russian projectiles struggle to penetrate Ukrainian air defenses — the May 24 barrage damaged the Rada and badly hit the Kyiv Opera and National Art Museum without changing anyone’s behavior.

Why is Latvia considered the most likely target for a NATO provocation?

Latvia recently saw its government collapse over an air-defense failure, has a population that is nearly one-quarter ethnic Russian with up to thirty-five percent speaking Russian at home, and sits adjacent to both Russia and Belarus. Combined with a new Russian law permitting force to “protect” Russians abroad and explicit threats from Russia’s UN ambassador, these factors make it a low-value, high-leverage target engineered to fracture NATO’s political will rather than seize major territory.

What is NATO doing to counter the Latvia threat?

On May 28, Germany and the Netherlands announced they will take joint command of NATO land forces in Estonia and Latvia within months, moving decision-making closer to the front for “mass at speed.” Two days earlier, NATO announced it will assign an entire corps to the region — potentially forty to sixty thousand wartime troops — bringing new air defense and artillery that will double existing defenses and likely close Russia’s window before it can build up sufficient force to act.