When the world's at stake,
go beyond the headlines.

Since the release of the U.S. 28-point draft peace plan in late November, many officials and observers have suggested that a ceasefire in Ukraine may be on the horizon. Undergirding this view is a growing consensus that Ukraine is losing the war as its troops cede territory and its economy and political order come under increasing strain. Indeed, as the war approaches its fourth year, Kyiv faces mounting attacks on critical infrastructure, recruiting challenges, and a corruption scandal that already forced the resignation of President Volodymyr Zelensky’s chief of staff. These challenges provide the backdrop to the ongoing ceasefire negotiations, and seemingly support Moscow’s narrative that time is on its side and that Kyiv should therefore sign a ceasefire negotiated by the Kremlin with the Trump administration.

Lost amid these Ukrainian setbacks is the fact that for the first time since the spring of 2022, Russia too appears interested in substantive negotiations — even if it has so far not shown much evidence of walking back from its maximalist demands. That willingness suggests that while Moscow has managed thus far to maintain the upper hand on the battlefield, the political, social, and economic difficulties it faces are also building, and — with them — the risks that the war poses to Russian political and social stability.

In that sense, the conflict in Ukraine is unfolding similarly to others in Russia’s long history of failed or inconclusive imperial wars. Several times in the past few centuries, Russian leaders launched wars of conquest against foes they misunderstood and underestimated, and with little appreciation of the larger international context. The longer each conflict dragged on, the more strain it placed on an under-institutionalized Russian economy and political system. In these earlier instances, the inability to sustain a long war compelled leaders to pull back, sometimes too late to save their regimes — a pattern that is not unique to Russia. President Vladimir Putin’s Russia therefore faces many of the same risks — both because it has chosen to fight an old-fashioned imperial war in the 21st century and because the Russian Federation suffers from many of the same structural weaknesses as its Imperial and Soviet predecessors. While it would be simplistic to say that Putin’s Russia will necessarily traverse the exact path they did, previous failed wars of conquest or other imperial interventions offer some insights into what the enduring consequences of Russia’s Ukrainian misadventure could be.

Analogies at War

To understand the strains that the invasion is placing on Russia, it is useful to compare the invasion of Ukraine with earlier examples of Russian imperial wars. While Putin constantly connects his war in Ukraine to the historical memory of World War II, Russia’s ongoing invasion of Ukraine more closely resembles failed Russian imperial wars of the past. The Crimean War (1853-56), the Russo-Japanese War (1904-05), World War I (1914-18), and the Soviet-Afghan War (1979-88) offer the most relevant analogies. All were wars of choice for territorial aggrandizement or other imperial interventions, which ended in military defeat followed by political upheaval.

Russia’s failure in these wars stemmed from common mistakes and shortcomings that also afflict Putin’s war in Ukraine. One common failing was to underestimate their foes’ military capabilities and societal resilience. Emperor Nicholas I expected the Ottoman Empire to quickly give way on his demand for a protectorate over Orthodox Christians in what is now Moldova and part of Romania, while Emperor Nicholas II and his commanders believed that the Japanese military could never stand up to a European great power. Similar hubris colored their assessment of the Ottomans in 1914-15, when they settled on seizing Constantinople and the Black Sea Straits as a war aim. Nor did Soviet commanders have much respect for the ragtag mujahedeen in Afghanistan.

Second, Russian leaders frequently downplayed the risks and impacts of foreign (i.e., Western) involvement that ended up prolonging the war and increasing the costs Russia was forced to bear. The landing of French and British troops in Crimea in 1854 forced Russia to fight on multiple fronts against better-equipped armies. British intelligence support enabled Tokyo to remain a step ahead of Russian plans throughout the Russo-Japanese War. While Russia declared war against Austria-Hungary in August 1914, it soon found itself at war with Germany, the Ottomans, and Bulgaria as well. A German-Ottoman blockade of the Black Sea Straits choked off Allied support, exacerbating the tsarist government’s inability to mobilize defense production. The Soviet invasion of Afghanistan prompted the United States, in uneasy alliance with Saudia Arabia and Pakistan, to arm the mujahedeen forces that ground down the Soviet army until General Secretary Mikhail Gorbachev ordered their withdrawal nearly a decade later.

With an economy far less dynamic that those of its Western rivals, Russia in each case found itself at an increasing disadvantage the longer these wars went on. As economic burdens and personnel losses mounted, so too did opposition not just to the war, but to the regime prosecuting it. Nicholas I died during the siege of Sevastopol (some contemporaries believed he committed suicide over his military failure), and his successor, Emperor Alexander II, would soon launch Imperial Russia’s greatest period of modernization and reform. High casualties and repeated military failures against Japan were key factors behind the demonstrations that sparked Russia’s 1905 Revolution. In 1917, Russia’s home front began disintegrating before its army in the face of persistent shortages exacerbated by the closure of the Black Sea Straits. Gorbachev characterized the Afghanistan debacle as a “bleeding wound” that sapped Soviet resources and stoked discontent at home. Military failure in Afghanistan was one factor in the demise of the Soviet Union itself that soon ensued.

Not Quiet on the Eastern Front

In all these earlier cases, hubris led Russian leaders to attack a smaller foe while ignoring the likely international implications and Russia’s own vulnerabilities. Putin’s Russia today finds itself in a similar position. The Kremlin dramatically underestimated Ukraine’s political resilience and military capability. Expecting Kyiv to capitulate in a matter of days, the Kremlin now faces a fourth year of grinding trench warfare in eastern Ukraine. While Moscow expected U.S. and European sanctions, it failed to anticipate the extent of the restrictions it would face, the cohesion (thus far) of the Western alliance, or the willingness of Ukraine’s partners to provide weapons and financial support.

Despite these failings, Putin’s Russia has done better than its predecessors at adapting under pressure, improving both its military performance and its international position, allowing it to weather sanctions and regenerate forces. These steps have allowed Russian troops to maintain a favorable battlefield position and bought the Kremlin time. What they have not done is resolved Russia’s underlying weaknesses and the tensions that wars of imperial expansion create: The longer the war lasts, the less effective these measures will become.

The Kremlin’s biggest success has been keeping Russia’s resource-dependent economy afloat amid unprecedented sanctions. The Bank of Russia has stared down pressure from oligarchs to maintain high interest rates that have headed off hyperinflation at the cost of further depressing growth. Inflation is low enough that the central bank made a small rate cut in October.

In its gradual, sometimes haphazard way, the Russian military has also proven adaptable. Unlike the Imperial and Soviet militaries’ reliance on conscripts, most of the Russian troops sent to fight in Ukraine are mercenaries, convicts, and well-paid contract soldiers (kontraktniki). Thanks to high bonuses paid to recruits, the Russian Defense Ministry has been able to meet and even surpass monthly recruiting goals this year. As either well-paid volunteers or from socially marginalized groups, casualties are less prone to spark a backlash compared to previous wars. Russia has also rapidly developed and deployed new drone, missile, and communications technology, enabling it to ramp up the pressure on Ukrainian forces and civilian infrastructure. This ability to adapt and, especially, to innovate technologically, is one that neither the Imperial nor the Soviet militaries were known for.

Another key advantage Putin’s Russia enjoys over its Soviet and Romanov predecessors has been the ability to prevent international isolation. Despite sanctions, the development of railways, road transport, and pipelines has allowed Russia to diversify its import and export routes more than its predecessors could. After dropping in the early stages of the war, the volume of rail and road transit across Russia has recovered over the past few years, while Moscow is developing new transit routes that bypass sanctions.

Russia also continues to sell crude oil and petroleum products on the global market, with China and India stepping in to offset volumes Russia can no longer sell in Europe. Russia is also able to bypass Western sanctions and export controls to access weapons (including drones, artillery shells, and rockets) from Iran and North Korea. While China has refrained from providing lethal weapons, it has become Russia’s most important source of dual-use goods subject to Western export controls, notably machine tools, components for explosives, and semiconductors. Defense production has not stagnated as it did during World War I, and Russia continues churning out drones, armor, and artillery rounds faster than its rivals.

The End of the Beginning?

Even with these measures, the strains on the Russian economy and political system are growing, much as during prolonged imperial wars of the past. The nexus between military failure and political upheaval is likely one reason for the history-obsessed Putin to pursue diplomacy with the Trump administration, as U.S.-Russian talks appear to be part of a strategy to lock in gains at the negotiating table while Moscow’s position remains favorable. When — and how — the war ends, though, the Kremlin will face a reckoning that it is ill-prepared to handle and that could have unpredictable consequences for political order in the country, though the nature of that reckoning could change depending on when and how the fighting in Ukraine stops.

The pace of Russian advances provides little basis for optimism that Russian forces will occupy the entirety of the four eastern Ukrainian regions Putin continues to demand anytime soon. Despite the likely fall of Pokrovsk in the coming weeks, Russia’s progress has been slow and come at prohibitive cost. A major offensive this past summer achieved little, despite Putin’s bravado. Russian losses remain upwards of 25,000 per month. Total Russian casualties since 2022 are likely above one million dead or grievously wounded — several times more than Moscow suffered in a decade of fighting in Afghanistan.

Russia does not have an inexhaustible supply of willing recruits — especially as funding to pay bonuses becomes more constrained. The alternative is to fall back on mobilization of conscripts, a stratagem the Kremlin tried and abandoned in 2022 after it sparked an outflow of fighting-age men, or the recruitment of mercenaries from the Global South. The exodus of Russian men, coupled with high casualties, has exacerbated Russia’s demographic decline. The situation has gotten so acute that the state statistics agency Rosstat this year stopped publishing monthly demographic data, following a measure last fall to delay some data collection for Russia’s next census. The disproportionate share of casualties suffered by ethnic minorities, including North Caucasian Muslims, Buryats, Kalmyks, Tuvans, and others, risks exacerbating ethnic tensions and demands for regional autonomy.

The Kremlin is also mortgaging Russia’s economic future, boosting defense production to unsustainable levels, while sanctions have accelerated Russia’s declining competitiveness and the de-modernization of its economy. Sberbank CEO German Gref claims economic growth has fallen to zero (though official figures remain slightly positive) despite the Kremlin spending more than 7 percent of GDP on defense this year. Bankruptcies are rising. The Moscow Stock Exchange has lost more than 40 percent of its value so far this year. By the end of August, the 2025 budget deficit had already exceeded $49 billion. Cut off from international financing and with its National Welfare Fund largely spent down, Russia has few options for financing its runaway spending short of raising taxes, which would further depress demand, or depreciating the ruble, which would stoke additional inflation.

Meanwhile, Ukrainian strikes are decimating Russia’s energy industry — the foundation of Russian prosperity and the source of the rents that Putin’s regime distributes throughout the elite. Recent strikes against tankers in Russia’s sanctions-skirting “shadow fleet” only add to this challenge, while newly imposed U.S. sanctions on Russian oil majors Rosneft and Lukoil have forced Chinese and Indian buyers to scale back purchases.

The structure of the Russian political system creates additional risk. Russia maintains what Henry Hale describes as a “patronal” model, where the Kremlin controls distribution of revenue streams to members of the elite as an inducement or reward for their loyalty. Putin’s regime has grown more personalistic throughout the war. Repression is mounting and elites are increasingly fearful for their own future. With the economic pie shrinking, fewer resources are available for redistribution, through legal means or otherwise.

Instead, Russia has witnessed a series of nationalizations, along with an intensive — if selective — crackdown on corruption. These campaigns provide short-term cash and allow the Kremlin to reward war supporters. They also, however, sever the link between the Kremlin and the officials and oligarchs who have long constituted the fabric of the Putinist system. Those who fear losing out can go to extreme measures.

Even Russia’s international partnerships — a key advantage Putin’s Russia has over its Imperial and Soviet precursors — create long-term vulnerabilities. Most significantly, the war is deepening Moscow’s strategic dependence on Beijing, including by shackling it to Chinese ambitions in the Indo-Pacific. While Beijing is willing to help Russia evade export controls, Chinese firms continue increasing the price they charge Russian customers for dual-use items, knowing that Moscow has few other choices. Russia now provides China high-end air defense, missile, and electronic warfare capabilities, and is helping to train Chinese forces for a possible invasion of Taiwan. Regardless of how the fighting in Ukraine ends, Russia will come out of the war poorer, militarily weaker (at least in the short-term), and more dependent on its erstwhile partners, especially China.

History Does Not Repeat, but It Rhymes

The odds of an even worse outcome will continue growing the longer the war lasts. Failure to reach a deal with the White House (and with Kyiv and Brussels) would leave the Kremlin facing a protracted conflict it is unlikely to win but also cannot abandon. Already, the post-2022 phase of the Russo-Ukrainian War has lasted longer than the Crimean and Russo-Japanese Wars, and a little longer than Russia’s participation in World War I. The strain on the economy and political system continues to grow. While the Russian economy currently faces Brezhnev-style stagnation, the risks of a crisis will mount as time goes on. A prolonged war also raises the risk of destabilization from intra-elite conflict, public opposition, and regional grievances.

Assuming it can negotiate a ceasefire, the Kremlin will face a different set of challenges, starting with the need to sell a deal that falls short of its initial goals. Ordinary Russians will want to know why the sacrifices they were forced to endure were worthwhile. The Kremlin will also struggle to reintegrate millions of traumatized veterans, including those released from the penal system to fill the ranks. Afghan war veterans (afgantsy) were a major component of the criminal underground that emerged in the years surrounding the Soviet collapse. The much larger number of Ukraine war veterans (including hardened criminals) could play a similarly de-stabilizing role today.

The mobilization economy will also have to be wound down. Even if the Kremlin intends to be prepared for war with NATO in 5–10 years as some analysts assess, current levels of defense spending are not sustainable. Cutting spending, though, will only exacerbate the elite infighting that has accompanied wartime mobilization, both at the center and in regions that have benefitted from new defense production. Nor will European sanctions be unwound anytime soon, irrespective of any deal between Moscow and Washington. The European market for Russian pipeline gas is probably gone for good. Sanctions or not, the wave of nationalizations and confiscation of assets the Kremlin has undertaken throughout the war suggests that political risk to investment in Russia remains high. Western firms are unlikely to return at scale, even if a ceasefire agreement provides for new commercial cooperation. In these conditions, the difficulties Russia faces in the short term are likely to be more chronic than acute, but will continue over time to undermine growth, political cohesion, and military reconstitution.

From the start of the full-scale war, Moscow has continually asserted that time is on its side and that the longer the war drags on, the more Ukraine will lose. That calculation may still pan out: The key variable remains the scale and extent of Western support for Ukraine.

Despite a larger economy and population base, in some ways autocratic Russia remains less capable of bearing the burdens of a protracted conflict than a democratic Ukraine backed by U.S. and European partners. Kyiv’s own theory of victory, articulated by former Ukrainian Defense Minister Andriy Zagorodnyuk, centers on the “strategic neutralization” of Russian offensives, forcing Russia to expend resources for trivial gains until the Kremlin is forced to back down.

Zagorodnyuk’s approach recognizes the inherent limitations of the Russian system. An under-institutionalized autocracy with an extraction-based economy is ill-equipped for a grinding war of attrition, especially one where ordinary citizens are asked to make sacrifices but have little stake in the outcome. Russia has seen this story play out before. As much as Putin portrays the conflict in Ukraine through the lens of World War II, it is modern Russia’s history of failed imperial wars — from Crimea to Afghanistan — that provides the best template for understanding how Putin’s Ukrainian misadventure could end.

Jeffrey Mankoff, Ph.D, is a distinguished fellow at National Defense University’s Institute for National Strategic Studies and a senior associate at the Center for Strategic and International Studies. He is the author of the books Russian Foreign Policy: The Return of Great Power Politics (2012) and Empires of Eurasia: How Imperial Legacies Shape International Security (2022).

The views expressed in this article are those of the author and are not an official policy or position of the National Defense University, the Defense Department, or the U.S. government.

**Please note, as a matter of house style, War on the Rocks will not use a different name for the U.S. Department of Defense until and unless the name is changed by statute by the U.S. Congress.

Image: RIA Novosti via Wikimedia Commons