In the spring of 2018, four years before his second invasion of Ukraine, Russian President Vladimir Putin delivered an unusual speech about the growing strength of the Russian military. “To those who in the past 15 years have tried to accelerate an arms race and seek unilateral advantage against Russia…,” he said, “I will say this: everything you have tried to prevent through such a policy has already happened. No one has managed to restrain Russia.”

At the time, the speech drew international attention primarily for Putin’s boasts about new hypersonic weapons designed to circumvent U.S. missile defense systems. But it also conveyed a more subtle message. Putin noted Russia’s successful intervention in the Syrian civil war, stated that the size of Russia’s conventional and nuclear arsenal had increased nearly fourfold, and asserted that its armed forces were “significantly stronger.” Putin also reiterated that “Russia reserves the right to use nuclear weapons solely in response to a nuclear attack, or an attack with other weapons of mass destruction against the country or its allies, or an act of aggression against us with the use of conventional weapons that threaten the very existence of the state.” Taken together, these comments exuded a strong sense of confidence in Russia’s ability to successfully counter any adversary—and perhaps a more muscular pursuit of national and personal goals. “Nobody wanted to listen to us,” he warned. “So listen now.”

Today, with the war in Ukraine moving in an increasingly dangerous and unpredictable direction, the question of Putin’s risk calculus has come sharply in view. Since early September, Moscow has faced a series of setbacks, including not only Ukraine’s dramatic territorial gains in the Kharkiv region but also its bold October 8 attack on the Kerch Strait Bridge connecting Crimea to Russia, imperiling a key Russian supply route. In response, Putin mobilized hundreds of thousands of additional troops, rushed to illegally annex territories that Russia does not fully control, and began a new wave of missile strikes on largely civilian targets, including Kyiv and other major cities. He has also repeatedly threatened to use nuclear weapons, noting that the United States had set such a precedent in Hiroshima and Nagasaki.

Putin’s threats about escalation have alarmed Russia’s European neighbors as well as the Biden administration. Yet his willingness to gamble on Russia’s military might did not begin in September, or even when he invaded Ukraine in February 2022. As the 2018 speech shows, his appetite for risk had been growing well before the current war. And although many questions remain about how far he is now prepared to go, an examination of how his thinking has evolved helps explain why he has taken this course and what he may decide are his most plausible options in the coming weeks and months. For the West, understanding Putin’s risk calculus may be as important as gauging Russia’s actual military strength in providing clues about what Russia will do next.

GOLDEN OPPORTUNITY

Before Putin’s 2022 invasion of Ukraine, he had built a reputation as a pragmatic risk-taker.  In Russia’s interventions in Georgia in 2008 and Crimea in 2014, Russian forces simply overpowered an undermatched and surprised adversary; in Syria beginning in 2015, Iran and Hezbollah did the heavy lifting on the ground while Russia offered materiel and air and naval power. In short, all three cases were relatively low-risk, high-gain situations with limited casualties. So how to explain Putin’s high-risk decision to invade Ukraine, putting some 180,000 soldiers on the front line, of which to date an estimated 15,000 or more have been killed?

A number of factors likely figured in Putin’s calculations: Russian security interests, a perceived window to advance broader geostrategic goals, and a desire to secure his place in Russian history. As is well known, Moscow cited security concerns as the principal driver behind the decision to launch the “special military operation” on February 24, namely, that Ukraine appeared to be sliding into NATO, as evidenced by Western military assistance and training and by Ukrainian President Volodymyr Zelensky’s open calls for NATO membership. But there was another impetus as well: Putin may have assessed that geopolitical circumstances offered a narrow opportunity to decisively break the seven-year stalemate in eastern Ukraine. As Moscow saw it, the United States was politically polarized; the American public was largely indifferent to Ukraine and wary of new foreign wars, especially after the messy U.S. departure from Afghanistan; longtime German Chancellor Angela Merkel was leaving office; the world was still preoccupied with the COVID-19 pandemic; and Europe had a heavy dependence on Russian oil and gas. Finally, Putin had a growing fixation with Russian history and was determined to secure his legacy as the great leader who restored core Slavic territories to Russia along with its rightful place as a global power.

Differences between Putin’s relatively low-risk invasion of Ukraine in 2014 and the full-scale invasion of 2022 provide important clues about how this thinking evolved. Putin’s first Ukraine invasion drew mostly on soldiers without markings—the unidentified Russian agents known as “little green men” and locally based naval infantry who set the stage for the takeover of Crimea. The rationale Putin provided was straightforward: to guarantee the “safety” of Crimea’s large ethnic Russian population from a nascent anti-Russian “fascist” Ukrainian government and to ensure Russia’s permanent control of Sevastopol, home of its Black Sea Fleet, regardless of who was in power in Kyiv. The creation of separatist pro-Russian beachheads in the Donetsk and Luhansk regions meanwhile gave Russia a means of trying to influence Kyiv’s future political orientation—and preclude NATO from considering Ukraine for membership.

It is possible that Putin’s 2014 moves were also part of a grander design, the first step toward incorporating much of Ukraine back into “Mother Russia.” Intriguingly, just months after the annexation of Crimea, Putin made public references to “Novorossiya”—the territory north of the Black Sea that was annexed by Catherine the Great in the eighteenth century —which, he noted, included Kharkiv, Kherson, Luhansk, Donetsk, Mykolayiv, and Odessa, areas that he described as “not part of Ukraine.” At the time, however, a large-scale invasion of Ukraine was out of the question; by Putin’s own account, Moscow had had to act quickly after the February 2014 fall of Viktor Yanukovych, the pro-Russian Ukrainian president, just to secure Crimea.

Moreover, events elsewhere likely redirected Putin’s focus away from Ukraine. Syrian President Bashar al-Assad’s request to rescue his tottering regime in the summer of 2015 required a big decision—but one with limited risk—to help preserve Moscow’s sole Middle East client regime. (Differences among Turkey, the United States, and other NATO members about which Syrian opposition group to support probably made Putin’s decision easier, since Assad’s definition of enemy combatants was simple: all regime opponents were “terrorists.”)

Of greater consequence for Putin was the unanticipated outcome of the 2016 U.S. election after Moscow had attempted to intervene on behalf of Donald Trump. With Trump in office, Putin must have concluded that there were too many potential geostrategic gains to be had to risk jeopardizing them with aggressive moves in Ukraine. Along with exploiting the growing political polarization in the United States, he could play to Trump’s skepticism of NATO and distrust of the U.S. intelligence community and possibly reach a deal on Ukraine that was favorable to Russia. In fact, backchannel contacts between a former senior Trump campaign official and a Russian intelligence officer about a possible deal on Ukraine continued into early 2018.

In Europe, Putin also saw growing leverage. During the Trump years, Europe’s institutional foundation was severely stressed on several fronts. The United Kingdom’s looming economic divorce from the continent suggested that the union was weakening; growing anti-immigrant sentiment had strengthened populist parties (and a like-minded leader in Hungary), whose views on social values and national identity aligned nicely with Russia’s; and NATO appeared to be riven by existential doubts. It was amid these developments that Putin gave his March 2018 address emphasizing Russia’s enhanced military prowess and implying a new willingness to use it. 

When exactly Putin decided to invade Ukraine remains a mystery, but by 2021, Russia was laying the military and political groundwork to make an invasion a viable option. Throughout the year, Moscow used planned military exercises to provide cover for a significant buildup of Russian forces along the Ukrainian border from an estimated 87,000 in February 2021 to some 100,000 to 120,000 by December. Then, an unscheduled military exercise with Belarus in mid-February 2022 put an additional 30,000 Russian troops on Ukraine’s northern border—on a direct route to Kyiv.

An equally important political signal was Putin’s startling 20-page treatise, “On the Historical Unity of the Russians and Ukrainians,” published on the Kremlin’s website in July 2021. In it, he asserted that historically, “Russians and Ukrainians were one people—a single whole”; that Ukraine never existed as a state; and that Ukraine’s current government was under “direct external control,” as demonstrated by the presence of “foreign advisers” and the “deployment of NATO infrastructure” on Ukrainian territory.

LARGER LOSSES, BIGGER BETS

Watching the Kremlin’s response to Ukraine’s military successes in September and October, one is reminded of the ancient Chinese proverb: He who rides a tiger is afraid to dismount. Eight months into a war that was supposed to be over in days or weeks, Putin’s invasion of Ukraine has morphed into a disastrous quagmire that potentially threatens his rule. His response to Russia’s accumulating battlefield setbacks suggests that he has few good options other than to raise the stakes and take even greater risks. The crucial question facing Ukraine and the West, then, is how far Putin’s escalation might go.

Key variables in his calculations are Russia’s ability to consolidate its territorial gains and Ukraine’s ability to maintain its offensive momentum. Ukraine’s success in taking back much of the Kharkiv region, attacking airfields and munition depots in Crimea, and bombing the Kerch Strait Bridge—a psychologically devastating raid on a key supply line and symbol of Putin’s Crimea success—underscore the significant challenge Moscow faces in simply consolidating the territories it still holds. These events also offered a preview of what Moscow will face in a counterinsurgency war, even if it manages to regain lost territory. Meanwhile, Western experts have highlighted Russian shortages of precision-guided munitions and even conventional missiles, which will further complicate this task.

Russia will have to significantly replenish and expand its fighting force if it hopes to make any forward progress on the battlefield, let alone subdue Ukraine. Putin’s August 25 decree increasing the size of Russia’s military by 137,000 was an early sign of a manpower problem, as was Moscow’s public acknowledgment in August that the Wagner private military group was an important entity in the war. But after Ukraine’s dramatic gains in early September, the troop shortfall issue became acute, and on September 21, Putin announced his “partial mobilization,” later clarified to include some 300,000 men. This startling draft call marked a critical inflection point domestically, with an estimated 100,000 to 200,000 potential draftees immediately seeking refuge abroad. Before September, the Russian military had primarily relied on recruitment and conscription of citizens from more remote—and ethnically diverse—regions of the Russian Far East and North Caucasus. Now even Moscow and St. Petersburg, where many children of the elite reside, are no longer shielded from the military realities of the war. Still, on October 14, Putin announced that 222,000 new soldiers would be ready for deployment within two weeks.

The other large battlefield factor is Moscow’s assessment of how well the Ukrainians are doing and Kyiv’s prospects for continued Western military and financial assistance. Zelensky has frequently expressed Ukraine’s need for such aid, including more advanced weaponry. As winter looms, he has also said Ukraine needs as much as $38 billion in emergency financial support to cover a growing debt problem. Much will depend on the political will of Western governments to meet these growing requests, which are critical to Ukraine’s ability to stay on the offensive and regain lost territory.

Within Russia itself, Putin will also have to weigh the impact of sanctions on Russia’s defense industry and energy sectors. Shortages of key chips and weapons components will increasingly hamper the Russian military’s fighting tactics and options; similarly, lack of key Western technologies—such as parts for oil drilling—will have longer-term effects on energy exports. As for the Russian economy, Western sanctions have contributed to a 14 percent inflation rate, constraints on foreign trade and international financial transactions, and the loss of much foreign investment.

Finally, Moscow faces an extraordinarily high casualty rate. The latest official Russian figure on war deaths, from September, is 6,534, but U.S. and independent estimates suggest the figure is almost certainly far higher. In July, CIA Director William Burns cited some 15,000 Russian deaths—the same number of troops the Soviets lost in ten years in Afghanistan. In August, the U.S. Department of Defense publicly reported 60,000 to 80,000 Russian casualties, and in mid-October, an independent Russian media site raised that number to 90,000. Few Russians find Moscow’s official data credible, as has been made clear by the mass exodus of prospective draftees since Putin’s “partial” mobilization.

How all these variables will play out in Putin’s calculations remains unclear. Little is known about what information and intelligence is provided to him, or the accuracy of that information.  Several reports have suggested that bad intelligence led Putin to believe that an invasion of Ukraine would succeed in short order, but blame must also be accorded to Putin himself: his 2021 treatise on Russia and Ukraine exposed his highly flawed assumptions about Ukrainians’ sense of national identity, their military capabilities, and their willingness to defend their country against a militarily superior adversary. 

THE NEW WINTER WAR

The twists and turns the war has taken since September underscore the dangers of drawing hasty conclusions about a Russian defeat. Ukraine’s impressive gains in the Kharkiv region and successful bombing of the Kerch Strait Bridge have prompted much commentary about a critical shift in momentum. But such assessments don’t take into account the full range of Putin’s options as he seeks to dismount the tiger. Indeed, just days after the bombing of the bridge, the multiday barrage of Russian missile strikes on Ukrainian cities and civilians brought the harsh potential of Russia’s punitive capabilities newly into focus. And if Putin’s claims about the numbers of draftees are true, his recent mobilization might help the Russians regain recently lost territory.

Moreover, the war between Putin and the West involves factors that are far beyond the battlefield. In this larger conflict, Putin clearly views winter as a key ally, one that allows him to weaponize Russia’s energy leverage over Europe. At a mid-October energy conference in Moscow, Gazprom’s CEO, Alexey Miller, noted that even in a warm winter, “whole towns and lands” could freeze for days or even weeks. At the same conference, Putin warned that the recent sabotage of the Nord Stream pipelines—an attack that many suspect was carried out by Russia—demonstrated that “any critical infrastructure in transport, energy or communication infrastructure is under threat—regardless of what part of the world it is located, by whom it is controlled, laid on the seabed or on land.” That message was delivered just a week after OPEC+, the consortium of which Russia is a member, announced its decision to reduce oil production by two million barrels per day despite extensive U.S. lobbying to keep levels higher. It was a not-too-subtle reminder to Washington that Russia’s energy leverage extends beyond Europe. Energy also figures in Putin’s current military tactics in Ukraine: missile strikes on Ukraine’s electricity grid and other infrastructure are likely intended to generate public pressure on Zelensky to negotiate with Moscow.

Should Putin’s winter strategy fail to result in new Western pressure on Zelensky to negotiate with Moscow, and should Russian forces continue to lose ground in Ukraine, Putin may well follow up on his oft-cited threats to “use all available means.” One possible option is large-scale cyberattacks on Western infrastructure, a threat that may already have been previewed in the distributed denial of service (DDOS) attacks on the websites of several large U.S. airports in mid-October. Preliminary assessments indicate that the attacks emanated from Russia, signaling that Moscow may be prepared to employ cybertools if the West continues to arm Kyiv with more advanced weaponry. 

But Russia could also use chemical weapons or tactical nuclear weapons to change the course of battle on the ground. Putin’s multiple references to nuclear weapons suggest he may believe that the psychological terror aspect induced by these weapons could be decisive—if not on the ground, then at the negotiating table. Such moves would entail great risk, as they likely would set off major Western retaliatory actions and start an escalatory spiral that neither Putin nor the West could easily manage. Moreover, should such a step fail to give Moscow the upper hand in Ukraine, mounting domestic criticism will inevitably force Putin to focus on an even more urgent priority: retaining power. If such a reckoning occurs, the views of Russia’s war hawks, including some of Putin’s closest advisers, may be decisive. As Stephen Sestanovich has noted, if any of them start to believe that Russia needs to cut its losses, Putin will need others with whom to share the blame. 

In fact, Putin has already positioned himself for such a scenario. Recall that just three days before the February 24 invasion, he orchestrated a nationally televised meeting of Russia’s Security Council in which each member voiced strong agreement with the need to take action in Ukraine. And in his announcement of Russian missile strikes after the bombing of the Kerch Strait Bridge, Putin noted that this move was proposed by the Defense Ministry in accordance with planning by Russia’s General Staff. Yet such efforts to share the political risk in these decisions can go only so far since it was Putin’s obsession with Ukraine and its inextricable bonds with Russia that set off the march to war.

As Kyiv and its Western backers assess Putin’s options in the coming months, one thing seems clear: Putin has various ways of prolonging the war. Combined with continued oil revenues, fresh manpower could sustain Russia’s war machine, possibly with extraordinarily destructive effects in Ukraine and beyond. At the same time, however, Putin’s options are narrowing. Over time, growing public opposition to the war could become difficult for him to contain as he approaches a 2024 election. Possible fissures within Putin’s inner circle will be harder to discern but more likely to threaten him directly. Continuing unified and robust Western support for Ukraine could well intensify this dynamic, but unless such political infighting or maneuvering by Kremlin insiders debilitates Putin, this war could go on for some time.