Smuggling for the Motherland? Using Ukraine’s Criminal Organizations Against Russia

Abstract

This article explores the possibility of Ukraine’s strategic use of domestic organized crime networks as an asset in its asymmetric war against Russia, using the case study of Operation Spider’s Web. By leveraging the logistical expertise, transnational reach, and deniability of criminal groups, Ukrainian security services could amplify their operational capabilities beyond conventional means. While effective, this collaboration raises complex risks for governance, legitimacy, and long-term postwar stability.

Introduction

On June 1, 2025, after eighteen months of preparation, Ukraine launched a covert attack deep inside Russia, causing upwards of $7 billion USD  in damage. Called Operation Spider’s Web, the attacks were executed by small drones that had been smuggled into Russia over the course of the past year through “covert logistical routes.” The drones were moved overland using trucks ostensibly hauling routine cargo – in this case, prefabricated buildings with drones concealed in the roofs.

Beyond the immediate damage, the secondary costs are significant: Russia must either accept the expense of fortifying or relocating countless military assets – those previously thought to be protected by ‘safe’ geography – or they must accept that these assets now exist on the front lines. Operation Spider’s Web was a clear success and  much has been written about it, but fundamental  logistical questions persist: How, exactly, did a production line in Ukraine deliver drones throughout  Russia? Who dropped the containers off on the side of the road or parked them at gas stations within striking distance of the Russian airfields? Who confirmed the assets were in position?

Open-source reporting and Ukrainian government characterizes this as a highly sophisticated, technical covert operation carried out by the Ukrainian Security Service (SBU). According to President Zelensky, the SBU set up a secret assembly line within Russia itself – so component parts were manufactured in Ukraine, smuggled across the border, transported to Central Russia, assembled, hidden in shipping containers, and then deployed. Some reporting suggests that the truck drivers who transported the goods were unknowing patsies, but the Ukrainian government has stated any personnel who were involved in the operation were safely back on the Ukrainian side of the border before the attack commenced, with the implication all personnel involved were Ukrainian intelligence and special operations.

However, the truth may be more complex. There has been a notable silence from both official sources and media reporting on how exactly the component parts and key personnel were transported from Ukraine into Russia and extracted again. Instead, articles gesture vaguely at these key resources being ‘smuggled’ both into and out of the country. To the casual reader, this is unremarkable. To anyone who has worked in logistics, particularly those involving hardened wartime borders, it raises a few more questions. This is a complicated and dangerous endeavor with challenges that only increase with volume. However, there are actors in the region with sizeable experience in moving goods, people, and weapons across complex spaces, including borders in wartime: Ukrainian organized crime.  Ukraine is home to some of the world’s most developed and sophisticated groups, which are busily making record profits moving all sorts of people and things back and forth between the belligerents. Could they have been the key piece in this logistical feat?

Organized Crime in Ukraine and Russia

Organized crime is generally defined under domestic legal structures, and as a result, the understanding of what ‘counts’ can vary quite widely. However in 2000, the UN Convention Against Transnational Organized Crime (UNTOC) established some basic conditions for signatory states: organized crime groups are “structured groups of three or more persons” which commit “serious crimes” (those crimes which are punishable with at least four years incarceration under the signatory’s legal system). This generally offers quite a bit of flexibility to the signatory government, neatly skirting issues of sovereignty and international organization overreach. In practice, transnational organized crime is nearly always some form of trafficking: the big three are drugs, arms, and people. Groups often move all three, along with a range of consumer goods. They are essentially highly sophisticated, innovative logistics companies specializing in illicit cargo.

Interestingly, while both Russia and Ukraine have both signed and ratified the Convention, in 2015 and again in 2022, the Ukrainian government informed the UN Secretary General that they would no longer guarantee enforcement of the Convention until the conflict with Russia was over. This disclosure can be read two ways: as an admission of uneven (legal) power projection by the Ukrainian government within their territory, particularly  as physical control of territory changes, or as a public statement that transnational organized crime groups and activities represents an irregular asset of opportunity for the country, and Ukraine will use (or at least will not rule out using) such groups and their activities for the state.

Indeed, it would not be much of change for the neighborhood: Russia has long been credibly accused of using both its domestic criminal networks and their Ukrainian counterparts to advance its interests. In the current conflict, Russia has used criminal networks extensively to avoid sanctions, maintain liquidity, and source critical goods. This relationships extends beyond rent-seeking behavior (taking a ‘cut’ of illicit proceeds) to include command and control activities over criminal activities. Less attention has been paid to Ukraine’s wartime use of organized crime, though it is well established that Ukraine has a similarly robust community of organized criminal networks.

Triangulating these statements with news reports and academic research, a feasible picture begins to emerge: in 2023, Agence France Press reported that many Ukrainian organized criminals cut ties and recalibrated allegiances in the wake of Russia’s invasion, developing explicitly patriotic business frameworks or displacing collaboration with their Russian counterparts to other countries. At the same time, the Ukrainian government deployed a two prong deterrence and inclusion strategy, conducting high profile disruptions of groups collaborating with Russian actors while offering amnesty for those who engaged in resistance activities. Taken in sum, there is overwhelming evidence that the Ukrainian government is at least on speaking terms with the leadership of its country’s underworld.

Crime as Irregular Warfare

Crime, particularly sophisticated organized crime, shares much of its DNA with other irregular warfare activities. Indeed, the 2024 Congressional Research Service Primer on Irregular Warfare argues irregular warfare includes “nontraditional activities such as… criminal activities.” Criminal activity and corruption function as key grey zone strategies for eroding competitor territorial control, distributing governance and maintaining control of domestic populations, generating intelligence, and even advancing state interests in a larger Great Power competition. Functionally, both illicit individuals and organizations are expendable, and outsourcing to them can often be faster and significantly less expensive than building up comparable abilities within the legitimate bureaucracy. Finally, action by criminal groups comes with attractive plausible deniability for the state, especially in contexts characterized by direct action. So while it may seem a risky and counterintuitive move for the Ukrainian government, particularly in support of such a key mission, crime groups can be an immense asset to the state, acting as a “force multiplier that bridges law enforcement, national security and international relations”.

States have  collaborated with organized crime groups before – historical examples abound: during World War II, for example, the United States Navy famously leveraged Italian organized crime groups in New York to collect intelligence, disrupt sabotage, and break organized labor work stoppages that would have impacted the operational tempo.  Today, states like Iran and North Korea regularly employ organized criminals to evade sanctions, while policymakers in Brazil rely on a power sharing agreement with gangs to ensure a modicum of stability in the country’s favelas. The traditional understanding of how states use and engage with these groups is an ad-hoc, transactional manner – essentially a ‘guns for hire’ scenario. However, this dynamic only captures a small piece of the spectrum. Politically violent nonstate groups collaborate and incorporate criminal groups as well. For example, paramilitary groups are often comprised of ‘dual hatted’ individuals: government affiliated irregulars moonlighting as criminals to support the cause, or vice versa. Both terrorist groups and states regularly target criminals for recruitment, with the explicit purpose of increasing the larger group’s capabilities and funding avenues. Such groups also work to develop their own illicit capabilities as well as collaborating with their criminal counterparts.

In this case, Ukraine’s possible use of criminal actors is not ideological but practical—a wartime expedient. These groups are quite literally the best in the world at doing precisely what was needed to execute Operation Spider’s Web: move key people and material across a hard border, transit through a hostile country, remain hidden for a time, then move them back across the border. This is a task that requires not only intelligence but preexisting relationships, nuanced on the ground knowledge, and experience moving through a complex space with a high risk of discovery. Of course, the state could develop these capabilities – running this sort of covert mission is the bread and butter of many special operations forces worldwide. However, in an environment of constrained resources, collocated with experts with a preexisting robust illicit network designed to do exactly this sort of task, why would the state not consider collaborating?

However, just because cooperation is feasible, questions remain. The risks—betrayal, discovery, or incompetence—seem significant.  The most obvious vulnerabilities center on trust and control: criminal groups seem inherently untrustworthy and using them in a mission of this importance and complexity is highly risky. Money alone cannot buy certainty because there’s always a chance of being outbid. Outsourcing means potentially giving up control over key operational elements, which can be particularly tricky in intelligence constrained or segmented contexts like this one. If discovered, the relationship has significant implications for the perceived legitimacy of the Ukrainian government, especially given the country’s history of problematic collaboration and corruption. Further, Russia could easily exploit the relationship ‘backwards,’ circumventing border controls to launch their own attack by simply paying off the same set of actors. Longer term vulnerabilities exist as well, some of which are acute in the Ukrainian context. Funneling money into criminal networks sets up a post-conflict challenger to the state, one that will have a large pool of resources in the form of returning veterans and internally displaced persons, as well as a region awash in weaponry.

To protect against defection and betrayal, a state interested in leveraging criminals should consider how criminal groups  build trust in illicit contexts. Central to such a working relationship is iterated interactions, social networks, and balancing incentives with risk, as well as limiting information to ‘need to know’. In this case, there is clearly an opportunity for repeated interactions between the Ukrainian state and its organized crime actors, as well as a strongly connected (if aging) social network.

While compelling reasons for criminal partnership may exist on the state side, why would criminal groups agree to cooperate? Surely getting involved in an action like Operation Spider’s Web exposes them to unwanted risk. Generally, criminal leadership and groups involve themselves in politics for the same reasons many of their licit counterparts do: desire for power, enrichment opportunities, even patriotism. Collaborating with the state offers money-making opportunities with a partner that is unlikely to default on their obligations, and which could be parlayed into future peacetime revenue via blackmail and extortion. In addition to hard cash, working with the state could open significant post-conflict opportunities, ranging from amnesty to superior positioning within the criminal ecosystem

Conclusions

Operation Spider’s Web is a masterclass in covert action, demonstrating Ukraine’s comparative advantage in innovation, adaptation, and flexibility. This operation has been publicly attributed to the work of the Ukrainian Security Service (SBU) and there is no open-source evidence to confirm other players beyond the SBU. However, Ukraine would be shortsighted if it wasn’t considering how to leverage its domestic assets (in the form of sophisticated transnational criminal organizations) in either this or similar operations. They would join a long line of states and violent nonstate groups that have done so in the context of irregular warfare. Such collaboration would not be without risk, particularly given Ukraine’s historical struggles with corruption and the public justifications Russia has given for their actions. In a war where perception matters nearly as much as firepower, any revelation of collusion with organized crime risks eroding international support and feeding Russian propaganda. The operation was executed brilliantly and creates interesting irregular possibilities for Ukraine, but its long-term consequences are yet to be seen.