Right up to the moment when President Vladimir Putin ordered his invasion of Ukraine, many Russia experts and analysts did not believe he would pull the trigger. Some, such as the Russian journalist and critic Yulia Latynina, argued that Putin was bluffing and would most likely back down at the first sign of real conflict. Others, including Hans Petter Midttun, a former Norwegian defense attaché in Ukraine; Andriy Zagorodnyuk, Alina Frolova, Oleksiy Pavliuchyk, and Viktor Kevlyuk of the Ukrainian Center for Defense Strategies; and several current and former Ukrainian officials, predicted that Moscow would opt to escalate the hybrid political and military warfare it has waged in eastern Ukraine for the last eight years rather than risk an all-out military assault. Nearly everyone who misread Putin’s intentions believed that the Russian president viewed the risks to Russia and to himself of a full-scale invasion as greater than the potential rewards. They assumed he would opt for cyberattacks, proxy warfare, and other more covert and deniable means.

Such assumptions had become so rooted in the prevailing view of Russia that it was easy to forget even these so-called gray zone techniques once seemed reckless and inconsistent with Putin’s apparent appetite for risk. The world has grown to expect Russian covert influence operations almost everywhere, for instance. But when Kremlin-backed hackers interfered in the 2016 U.S. presidential election, their actions struck many in the West as almost inconceivably brazen. I have been similarly surprised by Putin’s actions. After protesters toppled the Kremlin-friendly government in Kyiv in 2014, I assumed Putin would not overreact. Russia had deep enough political, economic, and sociocultural ties to Ukraine that he could afford to play the long game there, I reasoned. After all, that is what he did after Ukraine’s 2004 Orange Revolution, which had posed a similar threat to Russia’s sway over the country. But Putin confounded me and many other analysts with his willingness to use Russian forces covertly to seize Ukrainian territory.

The truth is that Putin has gradually evolved into an ever-higher-stakes gambler. Although many observers continued to assume that he measures the risks and rewards of particular actions as they do, Putin has grown more and more willing to take risks as he has come to believe that doing so pays off. He has not lost touch with reality or become “unhinged,” as some analysts have suggested. Rather, from his previous foreign interventions—especially in Ukraine and Syria—he has learned that boldness, surprise, and playing on his opponents’ fears of a wider war are the keys to getting what he wants. And that is why it is dangerous to assume that Putin’s future actions will mirror his past ones.


Putin’s appreciation for boldness, surprise, and playing on the West’s fear of war likely predates his presidency. In 1999, when Putin was director of Russia’s Federal Security Service, a small contingent of Russian peacekeepers made an unauthorized dash to Pristina, the capital of Kosovo, thwarting U.S. and NATO plans to take control of the airport. Russia and NATO were not in conflict with each other and were nominally pursuing compatible goals in Kosovo, but the administration of U.S. President Bill Clinton pushed NATO to intercept the Russian peacekeepers or beat them to the airport. In the end, however, the British NATO commander on the ground refused to challenge the Russians for fear of starting a “third world war.”

Putin took a similar lesson from his 2008 invasion of Georgia, when NATO forces also declined to confront advancing Russian troops. In the aftermath of Russia’s victory in that brief conflict, NATO showed support for Georgia by sailing a flotilla of naval ships to the country’s Black Sea coast. Russian analysts noted at the time that if NATO had wanted a fight, it could have easily defeated Russia’s Black Sea Fleet. But the alliance’s ships kept safely to the south of Russian ships, which Moscow saw as validating its bet that “even [U.S.] neoconservatives do not need a nuclear war,” as one Russian military official told the media.

Putin has gradually evolved into an ever-higher-stakes gambler.

Experiences such as these likely fed Putin’s risk appetite. But to understand why he graduated from risky but limited interventions such as those in Georgia in 2008 and Ukraine in 2014 to gambling on a full-scale invasion of Ukraine, one must recall what happened in Syria between 2013 and 2015. This period, during which Moscow capitalized on Western indecision to alter the course of the Syrian conflict, was a turning point in Putin’s risk calculus. It was when Russia shifted from its back foot to its front foot. In August 2013, President Bashar al-Assad’s regime used chemical weapons, crossing a U.S. redline and prompting Western plans to respond with airstrikes. But Moscow seized on an impromptu idea floated by U.S. Secretary of State John Kerry and persuaded Assad to announce he was willing to give up his chemical weapons, clearing the way for an agreement that averted U.S. military intervention. Overnight, Russia’s public narrative about Syria changed. Moscow went from passively defending Assad and attempting to deflect blame for his actions to congratulating itself on keeping the United States out of another dangerous conflict in the Middle East.  

Within three months, Putin had seized the initiative in Ukraine, as well. In November 2013, he convinced Ukrainian President Viktor Yanukovych to back out of a free-trade and association agreement with the EU; a month later, Yanukovych agreed to a Russian economic rescue package instead. Putin’s gambit faltered when Ukrainian protesters who opposed the deal with Russia forced Yanukovych to flee the country in February 2014. But the Russian president responded to the threat of losing influence in Ukraine by taking an even bigger gamble: occupying and illegally annexing Crimea. The rest of the world was forced to play catch-up, imposing sanctions as punishment in the wake of Russia’s transgressions instead of attempting to deter them ahead of time.


Russia’s increasingly risk-tolerant behavior both in Syria and Ukraine might have opened observers’ eyes to the reality that a new and bold Russian strategy in Syria was taking shape. Instead, Putin’s decision to intervene directly in Syria on behalf of Assad in September 2015 “surprised even the closest observers of Moscow’s foreign and security policy,” as the RAND analysts Samuel Charap, Elina Treyger, and Edward Geist have written.

In retrospect, most observers have come to explain Putin’s motives for the Syrian intervention in terms of the benefits it has brought Russia. For the price of a relatively modest deployment of mostly air and air-defense assets, Putin was able to turn the tide of the war in Assad’s favor and defend Russia’s own facilities and investments in Syria. Moscow demonstrated that it was a reliable partner to authoritarian allies and that it would no longer tolerate Western-sponsored regime changes such as those in Iraq and Libya. Russia gained valuable opportunities to test weapons and train personnel in live combat conditions without draining its budget. And the intervention made Russia a central player in the Middle East, ending a period of relative diplomatic isolation for Moscow that had followed its aggression against Ukraine.

Some of the benefits of Russia’s intervention in Syria look so self-evident in hindsight that it seems puzzling that almost no one predicted it in advance. But the blind spot for many observers was having outdated assumptions about Putin’s risk-reward calculus. It is hard to know exactly why so many experts assumed Russia wouldn’t get directly involved in the Syria fight. Assumptions, by their very nature, are infrequently spelled out and often unconscious. But one assumption cited by various analysts after the fact was that Putin would not commit forces to a fight outside Russia’s so-called near abroad. The Middle East was seen as peripheral to Moscow’s interests. And risking Russian lives in a nonessential war evoked memories of the Soviet Union’s disastrous experience in Afghanistan—a lesson, many analysts assumed, Putin would not want to repeat.

It is dangerous to assume that Putin’s future actions will mirror his past ones.

A related assumption was that Russian leaders would be unwilling to risk a clash with a vastly superior U.S. military by challenging it—or even placing Russian troops in proximity to it—outside Russia’s sphere of influence. Moscow had kept its military at a safe distance from the Americans during U.S.-led military operations in Serbia, Iraq, and Libya, even as it used a variety of diplomatic means to manage or try to thwart each operation. So when U.S. forces began operations against the Islamic State in Syria as part of an international coalition in August 2014, many assumed Russia would want to keep its distance there, too.

These assumptions weren’t unreasonable. Russia’s leaders had for many years acknowledged their country’s military inferiority to the United States and limited their geopolitical ambitions primarily to the post-Soviet space. Putin made a show of withdrawing from Russian facilities in Cuba and Vietnam shortly after 9/11. And even after the Syria conflict broke out in 2011, Russia’s actions appeared consistent with these assumptions. When the Assad regime began losing ground to its opponents in 2012 and early 2013, Moscow did not signal readiness to defend Damascus by force but rather focused on drawing down personnel and evacuating civilians from the country.

Even after the Assad regime recovered its battlefield advantage in May 2013, Russian officials continued to talk about diminishing Russia’s presence in Syria. Moscow was delivering arms and supplies to the regime and supporting it at the United Nations, but doing little else. Starting with the chemical weapons deal in September of that year, however, Russia grew more confident in its ability to mitigate risks and more convinced that its strengths and capabilities were equal to challenges and challengers it faced. A bolder, more brazen Putin was about to emerge.


It is often said that intelligence failures are failures of imagination. One way to break out of the cognitive trap of flawed assumptions is to imagine a seemingly implausible future scenario—state failure or civil war in a developed country, for instance —and then work backward, reconstructing the events that could have plausibly brought about this hypothetical future. Such an exercise can alert analysts to possibilities they hadn’t previously considered. It also can help them identify potential actors and factors—sometimes even so-called black swan events—that could contribute to an otherwise unlikely outcome.

Of course, it is also possible to reach seemingly implausible conclusions by working in traditional chronological order. One scholar who did so was Vladimir Pastukhov, a political scientist at University College London, who wrote in August 2013, “I will not be surprised if in the skies over Syria Russian [war] planes start to fly, and in Ukrainian territorial waters Russian submarines emerge.” His prediction of a Russia at war, six months before Moscow’s occupation of Crimea and two years before its intervention in Syria, appeared shortly after the Syrian chemical weapons attack that month. By contrast, U.S. media outlets at the time were highlighting the consensus view that Putin saw himself as powerless to stop imminent Western airstrikes in Syria.  

Pastukhov based his prediction in part on three trends that he saw as driving Russia’s choices: Russian leaders’ periodic compulsion to fight “unnecessary wars” such as World War I and the Soviet-Afghan war, Putin’s need to shore up his domestic support, and Moscow’s increasingly nationalist rhetoric about supposed enemies in Ukraine, Syria, and elsewhere. Pastukhov saw Putin as a “power junkie” who was becoming hostage to his own brinkmanship and might eventually push Russia into another unnecessary war that, like the previous two, could be suicidal to the regime or even to the state itself. In hindsight, there is enough to quibble with in Pastukhov’s prediction. Most notably, the war in Syria has not been harmful, much less suicidal, to Russia or to Putin’s regime. But Pastukhov’s prediction of the combined effect of trends that were visible to almost anyone was a rare example of success, rather than failure, of imagination.

Putin himself is not immune to faulty assumptions.

Moreover, Pastukhov’s description of Putin as a man increasingly driven to take risks helps explain the Russian leader’s willingness to chance it all with an all-out invasion of Ukraine. Necessary or not, Putin almost certainly sees the war in Syria as a resounding success. From his perspective, Russia’s military has been his most reliable tool for advancing his interests and persuading the West to take his demands seriously. His success has fueled bravado and confidence, if not overconfidence. Putin also knows that in the back of his opponents’ minds lurks a fear of escalation to nuclear conflict, which limits their willingness to challenge him militarily. Putin’s warning on February 24—moments before his military carried out its first strikes in Ukraine—that anyone who interfered would face “consequences you have never seen” was correctly interpreted as a threat to use nuclear weapons.

The lesson of Putin’s repeated surprises is that analysts must continually re-examine their assumptions. The best way to avoid being caught off guard is to identify one’s assumptions and consider what might happen if they turn out to be wrong. For instance, what if Putin isn’t bluffing when he obliquely threatens to use nuclear weapons to prevent outside interference in Ukraine? Analysts should also resist the temptation to explain events retroactively as having been inevitable, rather than the result of choices and circumstances. A classic example of this kind of flawed thinking is that the Soviet Union was destined to collapse when it did. Similarly, if Putin achieves his objective of a neutralized, non-NATO Ukraine, even at the expense of the lasting hostility of Ukrainians and punishing Western sanctions, some analysts will likely explain his war in retrospect as having been all but inevitable. It will not have been.

Finally, observers should be careful not to impose their own understanding of rational behavior on Putin or assume that he weighs risks and rewards as they do. Rather, they should seek to understand his evolving risk tolerance and sense of what works best to accomplish his goals. Putin himself is not immune to faulty assumptions. His past successes in Syria and Crimea have probably bred flawed assumptions about his ability to accomplish his objectives militarily in Ukraine. Pastukhov’s warning about unnecessary wars may yet catch up to Putin.

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  • CHRISTOPHER BORT is a Visiting Scholar with the Russia and Eurasia Program at the Carnegie Endowment for International Peace. From 2017 to 2021, he was National Intelligence Officer for Russia and Eurasia on the National Intelligence Council.
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