Escape From the Polar Owl: Russia’s Mafia Convict Soldiers in Ukraine

The village of Kharp, located 60 kilometers above the Arctic Circle, hosts Russia’s two northernmost prisons. They are both infamously brutal places. One, IK-3 or “the Polar Wolf,” is where the Russian dissident Alexei Navalny died last year. The other, IK-18 or “the Polar Owl,” is the more severe of the two: It is one of Russia’s seven prisons for convicts serving life sentences without the possibility of parole.

One of these convicts is Sergei Butorin, known as “Osya”—who, in 1994, united the remains of Moscow’s Orekhovo and Medvedkovo crime syndicates under his leadership. Osya’s gang was not particularly large or powerful, but his unpredictable band of hitmen was infamous for the excessive violence they employed. By 1998, Osya had made enemies of just about every crime boss in Moscow and, fearing retribution from all of them, he faked his death, had a plastic surgeon build him a new face, and fled the country. Osya continued to run the Orekhovo-Medvedkovo gang from abroad until 2001, when he was finally arrested in Barcelona and then eventually extradited back to Russia. A Moscow court convicted him of organizing at least 30 murders in the city throughout the 1990s, for which he was given a life sentence without the possibility of parole.

Only one of the prison’s other lifers is known to have ever left the Polar Owl on his own two feet, and yet, like other inmates in the Polar Owl, Osya still seems to believe he has a shot at getting out eventually. Osya’s first plan might have been to improve his position for an appeal by arranging the murder of the state’s witnesses, now including the former Orekhovo hitman Sasha the Soldier, who recently began to testify against him. But Sasha the Soldier’s murder has proved difficult to arrange from inside a notoriously isolated Arctic prison.

More recently, Osya has taken up a new approach to securing his release. As reported by the Telegram channel SHOT, in September 2024, he submitted a petition to be sent to fight in Russia’s war in Ukraine.

In August, I wrote for Lawfare about Russia’s use of convicts as soldiers in Ukraine. Russia began recruiting prisoners to fight in 2022, offering the promise of an eventual pardon. This was one of the Russian military’s strategies for keeping the war out of sight and out of mind for the majority of the Russian population, by obviating the need for a full mobilization. However, the strategy has frequently backfired. Pardoned prisoners have sometimes brought the violence of the war back home with them, committing horrific acts of violence with impunity. These highly sensational crimes have had the effect of making the war more visible in Russia—not less—producing a sense of social disruption the Russian state would have liked to hide away. The government has responded to this problem by changing its deal with convict-soldiers, trying to kill as many of them as possible on the front, rather than pardoning them. At some point, though, some of those troops will come home, and the consequences for Russia could be severe.

If someone like Osya heads to the front, he represents a more dangerous problem still—one that could potentially threaten the foundations of the Russian state itself. Many of Russia’s convict-soldiers have been drawn from the population of prisoners who were, like Osya, involved in organized crime in the 1990s. The Russian military has recruited not only low-level gangsters to fight, but even a number of well-known avtoriteti, or crime bosses of various levels—and, as historian Mark Galeotti has argued, the state has increasingly leaned on organized crime in a variety of other ways as well. In the midst of the war, the state’s growing reliance on organized crime has the potential to disrupt a set of careful arrangements and “understandings” (ponyatiya) that structure the peace between the Russian state and the Russian mafia.

These understandings that developed between the state and organized crime in 2000 were based on a kind of shared delusion: an agreement to pretend that the Russian state was capable of stopping the mafia. It was a delusion that most people, tired of the extreme of violence of the 1990s, wanted to sign onto. If the shared delusion of state power breaks, the cycle of violence could return again. Today, the state increasingly looks like a junior partner in its relationship with organized crime, as it loses the ability to bring down the hammer or set the terms of the relationship.

As Russia’s invasion of Ukraine drags on, the state has repeatedly favored pursuing the war effort over protecting the compromises that make the Russian state appear strong and capable. As a result, the war has slowly begun to erode the fragile stability of the Russian underworld. Nobody wants to find out what would happen if these arrangements were to actually fall apart—except, perhaps, the prisoners of the Polar Owl.

Deals Among Devils

For many years, Vladimir Putin built his legitimacy around the story, neither entirely true nor entirely false, that he had been the one to bring the traumatic era of Russia’s “wild 90s” to an end—an era embodied by men like Osya. More recently, though, Russia’s war in Ukraine has undone or put at risk many of the improvements in Russian life associated with this mythology. The war has shaken up Russia’s economy and has produced the kind of unpredictability and social chaos that Putin’s “vertical of power” was supposed to have ended in the early 2000s. It has also put pressure on the status quo that exists between the state and organized crime.

The Russian state under Putin is sometimes described as a “mafia state” or a “kleptocracy”—terms that cover a wide spectrum of meanings. Though the Russian state is certainly corrupt and at times mob-like in its arbitrary violence, and though many Russian politicians adopt criminal slang and a mafioso’s habits of fashion and interior design, the Russian government is distinct from the Russian mafia. Instead, as the sociologist Svetlana Stephenson describes, the relationship between the two is one of “reciprocal assimilation,” a symbiotic relationship in which “[c]riminal and state actors protect each other from economic competition and political challenges, jointly using their respective resources to reproduce the existing social order.” The product of a deal developed in the chaos of the 1990s, this relationship underpins the stability that Putin could claim to have brought about in 2000. It is this deal that is now under pressure.

In the 1990s, the Russian mafia emerged to fill the power vacuum left by the collapse of the Soviet Union. With the Russian state under Boris Yeltsin somewhere on the road from failing to failed, wildly different groups of people found they could quickly turn a profit by selling their ability to wield force. Collectives sold violence-as-a-service: providing the functions of property protection and dispute resolution otherwise unavailable through Russia’s weak courts and absent law enforcement. These groups, which sociologist Vadim Volkov famously termed “violent entrepreneurs,” included some existing participants in the old Soviet underworld—such as the vory v zakone, or thieves-in-law, the notorious Soviet prison gang—but also some fresh new faces, including veterans of the Soviet-Afghan war as well as body builders, karate practitioners, and even baseball players. Anyone in 1990s Russia who could swing a bat or throw a punch and wanted to make a bit of money while doing so had a strong incentive to organize a criminal conspiracy.

Because the Russian government of the 1990s had lost its monopoly on the legitimate use of force, these new groups became a kind of alternative, for-profit state. If you were being cheated in a business deal, or if you had reason to be concerned for the structural integrity of your kneecaps, it was always a better bet to pay for private security instead of trying to call the police or file a lawsuit. As such, groups that could offer reliable violence at a good price became immensely powerful, competing for legitimacy with the weak state.

Whatever wealth and power they enjoyed, though, the life of a violent entrepreneur was typically brief and difficult. The city of Yekaterinburg, sometimes considered Russia’s “capital of crime,” is famous for its vast mafia cemetery, full of the elaborately tacky graves of men in their 20s and 30s who died in Uralmash’s endless skirmishes with the Tsentr gang. At the end of the 1990s, these Russian mafiosi had become rich men, and they were not getting any younger. In 2000, tired of violence, these gangsters seem to have struck a deal with Russia’s new president, Vladimir Putin, that went something like this: If they agreed to give up some of their power, then the state would also protect their property and resolve their disputes without them having to resort to deadly violence. Any gang that did not challenge the power of the state would be allowed to maintain its operation and its vast accumulated wealth. The private market of violence would become one of many business interests putting pressure on the Russian state, but one that did not challenge the power of the state itself.

Some Russian mafiosi did not submit to this deal. Our friend Osya, who is now locked away in the Polar Owl, had become leader of what was left of the Orekhovo gang after 1994. In 1998, he ordered the murder of a police investigator. After fleeing the country, he continued to order a number of murders in Moscow from the safety of his perch in Spain. In response, the law came down hard on the remaining Orekhovo gang members—quickly rounding up just about all of them and sentencing them to long terms in prison.

For most of these violent entrepreneurs, though, this arrangement was a carrot without a stick. The state’s show of force against those who continued to operate under the old system of extreme violence made it easier for the rest of them to set down their weapons, something they desperately wanted. They were agreeing to a shared delusion that the state was powerful enough to stop them, so they would have an excuse to stop killing each other. The violence didn’t disappear entirely—mob bosses continued to occasionally murder one another—but it became less common, more subtle, and much more predictable. Local crime bosses became pillars of the community, diversified into legitimate businesses, turned into bankers and sometimes politicians—including, in many cases, the regional representatives of Putin’s party, United Russia. They could stop checking under the Mercedes every morning for a car bomb and could take a nap by a pool in Cyprus without keeping one eye open.

Mobilizing the Mafia

The deal has survived a number of disruptions and minor crises, through the murders of major crime bosses and other challenges to which the state responded with force. It has held relatively strong because it is a win-win for the state and for organized crime—though not for Osya, 60 miles north of the Arctic Circle.

The deal has persisted even though, over the past decade or so, the state has asked more and more of organized crime. The Russian state has extended its reach around the world, through private military companies like Yevgeny Prigozhin’s Wagner Group, while maintaining its plausible deniability. It has relied on the underworld to organize and carry out cybercrimes and to smuggle sanctioned cheeses into the country. In exchange, the world of organized crime has been granted a set of economic incentives, as historian Mark Galeotti has chronicled—including blank bank accounts that make it easy to launder money or move it off shore, and free rein with crypto. Over the past decade, the Russian state has put the underworld to work, but in return, criminals have been well compensated.

However, after the full-scale invasion of Ukraine, the state has begun to ask for even more, without offering as much in return—putting pressure on the long-standing deal. The war has massively increased the state’s needs, while its ability to provide economic incentives has simultaneously decreased. This reliance on organized crime was perhaps most visible when the Russian military leaned on the Wagner Group to fight in Bakhmut and Soledar, but criminal groups also fuel the war machine in other ways—notably, by laundering state funds and smuggling goods in and out of the country. Yet the war has also cut off some of the lucrative smuggling routes that Russian criminals profited from, and sanctions have made it harder for wealthy crime bosses to easily launder their money or to access their property and resources in Europe and America.

This dynamic is additionally complicated by the Russian state’s need to bulk out its military forces by recruiting prisoners to fight. Doing so has required additional deals and compromises to ensure the compliance of organized crime. According to Olga Romanova, a prison rights activist in Russia, many prisoners, especially those involved in organized crime, had initially been concerned that to volunteer to participate in the war effort would violate the codes of the vory v zakone—which many contemporary Russian gangsters still admire and try to emulate, though the Soviet prison gang is long extinct. In response, at the beginning of 2023, several Russian prisons showed a video address by mobster Zakhariy Kalashov, known as as Shakro the Younger—who is considered by some to be one of the last remaining vory. In the address, Shakro the Younger expressed his hope that prisoners would sign up to join the Wagner Group in the new year. Within a year of recording the video, Shakro the Younger and several members of his large and powerful gang were released from prison for various “medical reasons.”

Shakro’s video had been aired immediately following Putin’s New Year’s address, the timing of which seemed to suggest some degree of unbalancing in the hierarchy of organized crime and state. Among its prisoner-soldiers, at least, the Russian state must now rely on Shakro’s authority, because it can’t entirely rely on Putin’s.

A number of former “violent entrepreneurs” have signed up to fight, from a large number of local crime bosses up to even some of the world of Russian organized crime’s most significant figures. With long sentences in harsh conditions, they are often the ones who most stand to gain from the possibility of a pardon. Among the Russian soldiers who died in Ukraine in 2022 and 2023 were Sergei Maksimenko, the leader of the city Penza’s Olimpia gang, who famously ordered the killing of rival gang members at a local bar in 2003 using baseball bats and hunting rifles; and Andrei Berezhnykh, the leader of a small gang based near the city of Saratov, which in 2003 attacked the Saratov television station STV with a grenade launcher. Maksimenko and Berezhnykh are only two of many.

Though it may seem like simply an extension or evolution of earlier arrangements between the Russian state and mob bosses, this use of prisoners drawn from the world of organized crime complicates the relationship in a host of ways, creating a dangerous set of unbalances and disruptions. The release of a powerful crime boss like Shakro the Younger, along with much of his gang, for example, requires organized crime to make more room at the top. Since his release, Shakro has apparently reasserted his former position in the Russian underworld by forcibly “dismissing” his deputy Badri Koguashvili (known as Kutaisky). Ongoing conflict between the two has led to some beatings and other forms of violence—and has even spread throughout the Georgian and Azerbaijani underworlds in which Shakro and crew have ties.

The Return of the Wild 90s?

As I wrote previously, the state has developed a method of dealing with the problems of former prisoners who returned home from the war and went on to commit violent crimes: It tries to kill as many of them at the front as possible. But this solution creates its own difficulties when the prisoners in question are major figures in the world of organized crime. For one thing, it doesn’t always succeed, and that tends to make them angry. Dmitri Vedernikov, nicknamed Vedera, the leader of the Mestanatovskie gang, based in the Russian city of Chita, gave regular updates about his experience at the front on social media and to several local news outlets. Vedernikov posted that he had been badly wounded and hospitalized a number of times while in Ukraine, but the military had refused to discharge him or send him back home, instead ordering him back to the front even when he was still on crutches. He told Chita.ru that he believed that the military was actively “trying to get rid of [him.]” Last month, he escaped from the front, and no one seems to know where he is now.

The release of prisoners to fight at the front has led to the resurgence of the Trassoviki gang, whose members were arrested in 2011 through 2013 after the discovery of the mummified body of one of their victims in a barrel full of concrete at the bottom of a ravine in Tatarstan. The gang’s leader was killed in 2022 after volunteering to fight for Wagner, but his right-hand man, Sergei Zuzlev, survived to be pardoned and has revived his old gang.

Both the death of an avtoritet and the return of one can alter the fragile balance of power that lets various gangs maintain their truces and avoid violence. The biggest challenges to the peace of the Russian underworld have tended to come from the deaths of powerful mob bosses. And now, a large number of gangsters have died in Ukraine—like Igor Kusk, who had led a gang of hitmen drawn from his fellow Soviet-Afghan war veterans in the Tatarstan town of Nizhnekamsk, and died in Bakhmut in 2022. (Some 700 people attended his funeral. Despite, or perhaps because of, his murder convictions throughout the 1990s and 2000s, Kusk had still been a major leader in the local veterans’ movement.) Each death has the potential to upset the careful balance of power that holds the criminal world together. Deputies and second-in-commands now have an incentive to violently compete for the top job, testing the limits of the deal with the state.

However, the use of prisoner-soldiers has also made it far less possible for the state to establish where the limits now lie. Not only is the state running out of carrots, but it is also running out of sticks. Andrei Seleznev (known as Selya), one of the heads of the Herat-Ural gang, which ran much of Nizhny Tagil throughout the 1990s, was able to avoid a murder charge by signing up to fight in Ukraine in July 2025. The ranks of volunteers also include several members of the brutal Krasnodar gang run by the Tsapka brothers, which essentially seized control of a small town and then massacred a farmer, his family, and his houseguests when the farmer refused to pay protection money in 2010. This level of violence might have been typical of the 1990s, but by the 2010s, it broke the terms of the deal, and the state responded forcefully, arresting most of the gang. Two of the killers later signed contracts to fight in Ukraine. One died, while the other received a pardon and returned home—where he is now working as a driver and bodyguard for the Tsapka family.

Prison terms, in other words, no longer hold the significance that they once did. It is hard to say, if the state can’t bring you in or punish you, how it would set what the limits are for organized crime.

But still, there are limits to who the state will release. Osya’s petition to be sent to the front last September was actually his second. In 2022, the Wagner Group rejected his similar request on the grounds that he was a convict serving a life sentence, a category of prisoner they did not generally accept. Under new laws from 2023, there is no official prohibition against the release of prisoners sentenced to life without parole—though they generally require a special exemption of some kind, which Osya has thus far not been granted.

Why would releasing Osya be a step too far? He was considered something of what in mafia slang is called a bespredelshchik, or “limitless” person—essentially, a chaos muppet, a person who believes the rules don’t apply to them. After the death of Orekhovo’s original leader, Sylvester, Osya participated in a massive internecine struggle between members of Orekhovo for control. Osya’s band targeted enemies indiscriminately, whether they were enemies, allies, or even members of his own gang, and they did so without offering a warning or attempting to settle things first. This behavior went beyond the norms of organized crime, the established rules of engagement, even of Russia’s wild 90s, and represented exactly the kind of chaos and unpredictable violence that the state, and crime bosses, hoped to end in 2000. Allowing Osya to leave prison would risk signaling that the limits put in place since the 1990s no longer apply and that the situation in Russia could be tending toward becoming one of bespredel.

A broken deal would not look exactly like the 1990s, but whatever came next would not be good. A potential vision of this future came in 2023, when one violent entrepreneur—the late Prigozhin, who formerly led the Wagner Group—tested the actual strength of the state when he marched Wagner troops toward Moscow over a dispute with the Ministry of Defense. He unexpectedly found himself with a clear path to the capital when the military never showed up to stop him. Instead of confronting the yawning absence of the state, he chose to turn around, and died a month later in an explosion orchestrated by the Kremlin.

Since the beginning of Russia’s invasion of Ukraine, the rates of contract murder in Russia have gone up—though not yet to the level of the 1990s. But 1990s-style gang violence has gradually grown more visible—such as the 2024 armed raid over a business dispute at the Moscow office of the e-commerce company Wildberries, which many people described as reminiscent of the 1990s. (The men convicted of the shooting also signed up to join the war.) In the past few years, there have also been a string of mysterious suicides of high-level CEOs and stuff, which might be suicides but could also be assassinations. As the state loses its ability to wield force, it risks demonstrating that if organized criminal groups wanted to stop respecting it, they could. Nobody wants the old deal to fail, and it has managed to hold before through a variety of conflicts and pressures. But the war is creating the conditions that could cause it to finally dissolve.

The state’s continued commitment to the war in Ukraine will likely keep eating away at what remains of Russia’s stability. Having been rejected previously, Osya filed his second petition in late 2024, proposing that he should be granted a special exemption or reduced sentence, because the state needed him at the front. While Osya pointed rather innocently to the value of his previous military experience—the source, he suggested, of his facility with a wide variety of weapons—others have pointed out that his previous “leadership experience” at the head of a band of deranged murderers might be of more value. Several Russian outlets that reported on his petition seem to have believed, like Osya, that this was an argument that the Russian state would find convincing—several of them described his request under the premature headline “the leader of the Orekhovo crime syndicate is going to the SVO,” meaning the Special Military Operation in Ukraine.

The widespread belief that the state needs his “leadership experience” suggests the fragility of the status quo. Osya, for one, seems confident that the Russian government will soon call on him, as they have called on other figures from the world of Russian organized crime. Reportedly, Osya has been preparing himself to go to the front by doing push-ups and regularly meditating.  A few months ago, he appeared in a court in Moscow, having agreed to testify in a trial related to his activities in the 1990s. In the courtroom, Osya’s smile gave the impression of a man who has set a trap that’s about to spring.