The signs of failure in Russia’s invasion of Ukraine are readily apparent: the tattered reputation of its military as a modernized, overpowering fighting force; its tattered economy; and a Western alliance more unified than at any time since the worst tensions of the Cold War.
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But what is less appreciated is that this is only the latest and potentially the most spectacular in a series of failures suffered by President Vladimir V. Putin of Russia in Ukraine. If Afghanistan is the “graveyard of empires,” Ukraine is where Mr. Putin’s imperial ambitions consistently founder.
In fact, the main reason the Russian leader took such a potentially self-destructive step as a whole scale invasion, some analysts believe, was to reverse a long line of fiascos dating back to Ukraine’s so-called Orange Revolution in 2004, during the early years of Mr. Putin’s presidency.
“He has been obsessed with Ukraine since the early 2000s because Ukraine became the field where he kept losing, the only field where he kept losing,” said Mikhail Fishman, the former host of a political talk show on TV Rain, the now shuttered independent television network.
Mr. Putin has long plotted to undermine Ukraine, overtly and covertly, and has notched some wins along the way. He has kept the country bogged down in a grinding war in the east, sowed discord among the political class and damaged its infrastructure with experimental cyberattacks — techniques later exported to the United States and elsewhere.
But on at least three significant occasions when Mr. Putin intervened directly to bring Ukraine under Russia’s heel, he was thwarted.
There is always the chance that he could prevail this time, whether by reducing Ukraine’s cities to rubble or seizing a large chunk of the country in the east and south and declaring victory. Support for the war at home seems to be strong.
But even those outcomes would bring costs, reinforcing Ukrainians’ hatred for Russia, cementing Moscow’s status as a pariah to the West and almost certainly requiring a lengthy and expensive occupation.
History has tended to smite Russian leaders who launched what they wrongly anticipated would be short, victorious wars. The Russian Revolution that ended 300 years of Romanov rule erupted a few years after Czar Nicholas II lost a disastrous war against the Japanese, while the Soviet Union collapsed in the wake of its debacle in Afghanistan.
Some analysts believe that Mr. Putin is risking a similar fate. “He will lose Russia because of Ukraine,” said Mr. Fishman, who has just finished a book about why democracy failed to take hold in Russia after the Soviet collapse. Others are less emphatic, especially in the short term, and note the popular signs of support for him inside Russia. Still, they caution that Mr. Putin is uncharacteristically playing a poker game with an unpredictable ending.
“This has been a major failure in Europe’s biggest land war since 1945, and that is a big failure,” said Clifford Kupchan, chairman of the Eurasia Group, a political risk assessment firm. “I would not bet futures in Russian political stability over a five-year period.”
While Mr. Putin has publicly emphasized the security threat posed by a westward leaning Ukraine as a reason for going to war, others say his deepest concern is the possible political fallout from living next door to a boisterous democracy with decent economic prospects.
“Putin’s ultimate nightmare is a color revolution in Russia, and that is the lens through which he views people voting in Ukraine,” said Mr. Kupchan. “Because it is so close, culturally, the threat of contagion as he perceives it is even greater.”
Mr. Putin’s successes are legion, especially his entire career arc from an obscure, midlevel intelligence agent — forced to drive a taxi to make ends meet after the collapse of the Soviet Bloc — to becoming one of the longest-running leaders ever to occupy the Kremlin.
Yet in Ukraine, Mr. Putin, 69, has taken repeated missteps.
In 2004, he campaigned personally in the presidential election on behalf of his preferred candidate, Viktor F. Yanukovych, whom he twice congratulated on his win. But widespread accusations of voting fraud sparked a nationalist backlash and the Orange Revolution, with street protests culminating ultimately in the election of Viktor A. Yushchenko (who was poisoned during the campaign) as president in a Western-oriented government.
In 2006, Mr. Putin tried to wrest greater control over — and profits from — the natural gas distribution system carrying Russian supplies across Ukraine to Europe, creating an uproar by cutting the flow in the middle of winter. He backed down when it became apparent that he risked losing energy markets in Europe if supplies of Russian gas could not be relied upon.
In 2009, he attempted to effect a cabinet reshuffle in Kyiv that would have allowed his allies to dominate the government, but the effort collapsed.
Mr. Putin made his gravest error before now in 2013, when it looked like Ukraine would successfully slip Russia’s orbit by signing an association agreement with the European Union. To head that off, he dangled a $15 billion loan that Mr. Yanukovych — by then the legitimately elected but incorrigibly corrupt president — accepted. As in 2003, that triggered massive street protests on Kyiv’s Independence Square, or Maidan. After police violence encouraged by Moscow failed to deter the demonstrators, Mr. Yanukovych fled to Russia in February 2014.
Mr. Putin called it an American-inspired coup and invaded Crimea, eventually annexing it, and kindled a separatist war in the Donbas region, the resource-rich rust belt of eastern Ukraine. He thought he had found a means to dominate Kyiv in a proposed treaty called the Minsk agreements, which would have given the separatists veto power over important central government decisions. But the deal was never implemented, and the war became a grinding impasse that by 2022 had killed 14,000 people, many of them civilians.
As the failures piled up, Mr. Putin began to denigrate Ukraine. He claimed that it was not a real country, but an artifice cobbled together by Lenin using different bits of Russian land, and in recent years said it was presided over by a “Nazi” government that Ukrainians — particularly ethnic Russians in the country’s eastern parts — would be glad to see overthrown.
Curiously, Mr. Putin sketched out his ultimate plans for Ukraine in 2014, after he annexed Crimea. While holding court at his annual televised town hall meeting, he made a surprise pronouncement about “Novorossiya,” or New Russia, an arc stretching along the entire coast and eastern side of Ukraine.
“I would like to remind you that what was called Novorossiya back in the czarist days — Kharkiv, Luhansk, Donetsk, Kherson, Nikolayev and Odesa — were not part of Ukraine back then,” he said. “Russia lost those territories for various reasons, but the people remained.”
In the current invasion, the Russian military has attacked all six cities he mentioned. Yet, leaving aside Luhansk and Donetsk in the separatist regions, Russian troops have managed to capture only Kherson, with the rest resisting fiercely, apparently to Mr. Putin’s surprise.
The example of Novorossiya provides a clue to as to why Mr. Putin failed so consistently in his efforts to subjugate Ukraine.
In the late 18th century, when Catherine the Great toured the same newly conquered lands of Novorossiya, the phrase “Potemkin village” was born to describe the facades erected by one of her generals to conceal the region’s grinding poverty and backwardness.
When it comes to Ukraine, analysts say, Mr. Putin seems to have constructed a Potemkin village in his own mind, deluding himself that Russian-speaking, southeastern Ukraine, home to millions of ethnic Russians, yearned to be part of the Motherland again.
What Mr. Putin failed to recognize is that 30 years of democratic elections had gradually engendered a sense of nationhood among Ukrainians, analysts said. People realized that they enjoyed far greater freedoms in their new country, despite its corruption, than under the oppressive autocracy that Mr. Putin sought to impose.
When the invasion failed to produce the quick results Mr. Putin envisioned, bogging down amid numerous self-inflicted wounds, analysts say Mr. Putin turned to the wanton destruction of Ukraine — punishing its 44 million citizens for their long history of rejecting his attempts to incorporate the country into his Russki Mir, or Russian World.
“I think he sees Ukrainians as traitors now, because they are not falling into his vision of Russki Mir,” said Fiona Hill, an adviser on Russia to President Trump and his two predecessors, as well as the co-author of a biography on Mr. Putin and currently a senior fellow at the Brookings Institution.
Mr. Putin and his Kremlin cronies have long blamed their failures on American arrogance, deceit and manipulation, the standard fallback position for anyone from the Soviet-trained establishment. In the current disaster, they have again raised phantom fears of NATO missile bases and chemical weapons labs in Ukraine.
But as many analysts have observed, powerful people who spread such fictions often come to believe their own lies, and in the absence of dissenting voices, blind themselves to the realities they need to grapple with. For Mr. Putin, his greatest blind spot has arguably been Ukraine.
“If you live in the world where people actually matter and their voice matters, that is a different world from Putin,” said Mr. Fishman. “It is always about some secret deals that the powerful running the world achieve.”
Ultimately, the invasion seems already to represent another failure for Mr. Putin in Ukraine, perhaps his greatest, wrecking his quest to become the historical hero who reconstituted the Russian Empire.
“Without Ukraine it means nothing,” said Mr. Fishman of Mr. Putin’s quest. “He will never get political control over Ukraine, it is out of the question.”