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Russian President Vladimir Putin delivers his annual news conference in Moscow in December.

Russian President Vladimir Putin delivers his annual news conference in Moscow in December. (Andrey Rudakov/Bloomberg)

When President Vladimir Putin yelled, “We will win!” at a Red Square concert to celebrate his illegal annexation of Ukrainian lands on Friday, he projected the desperate hubris of a man terrified of defeat.

In Putin’s mind, he cannot lose. But multiple battlefield defeats and national fury over a botched military mobilization have broken a taboo in Moscow on discussions about what would happen if Putin did lose — not just the war, but his seeming bid to be leader-for-life, according to four members of Russia’s business elite. Kremlin-watchers, inside and outside the capital, are asking: Who might come next?

The possibilities range from the obvious — Prime Minister Mikhail Mishustin is legally first in the line of succession — to the utterly unpredictable: Some Putin supporters fear the country could break apart without his authoritarian hand at the helm.

Putin himself came to power through a quasi-legal succession process — appointed as deputy prime minister and then acting prime minister by President Boris Yeltsin, who resigned within five months, catapulting his handpicked successor into the presidency.

It remains to be seen whether Putin will enjoy a similar opportunity to orchestrate his own succession. And if Mishustin, a former director of Russia’s federal tax service, ever becomes president, he is widely expected to be a short-term placeholder.

Names mentioned as potential successors include the Security Council secretary, Nikolai Patrushev, former president Dmitry Medvedev, longtime Moscow Mayor Sergei Sobyanin and Patrushev’s son, Dmitry, now agriculture minister.

Speculation about Putin’s theoretical downfall has grown as the president has been squeezed from abroad, by international condemnation of his war in Ukraine, and at home, by rising pressure from pro-war hawks and pro-Kremlin propagandists irate over military losses.

There are also rising squabbles among the elite. Chechen leader Ramzan Kadyrov and Russian oligarch Yevgeniy Prigozhin, the founder of the Wagner mercenary group, have bitterly attacked Russian military commanders for the failures in Ukraine, triggering open speculation that Defense Minister Sergei Shoigu, once tipped as a likely Putin successor, will be replaced.

Neither Kadryov nor Prigozhin is seen as capable of marshaling the support across Russia’s powerful security services or in the broader elite to claim the top job. But they are reminders of how much worse than Putin a future leader could be if the Kremlin loses control, yielding a chaotic, brutal power struggle instead of a carefully manipulated succession in the country with the world’s largest nuclear arsenal.

Many Russia analysts doubt that Putin will fall unless he faces new disasters such as mass casualties, or economic hardship, leading to widespread social unrest.

“There’s a lot of people who I think are fed up with the current situation. They think that Putin has passed his sell-by date,” said Mark Galeotti of University College London’s School of Slavonic and East European Studies. But for now, Russia’s pragmatic, kleptocratic elite see that “the dangers in moving against Putin vastly outweigh the risks in just keeping your head down and hoping things work out,” Galeotti said.

“What we’re seeing is a regime which is still very strong and solid,” he said. “Putin still has control of the security apparatus, and that’s probably the most important individual factor, but it’s brittle.”

Andrei Soldatov, an analyst and expert on Russia’s shadowy security services, said that he is “skeptical about succession games. People are angry, of course, but that doesn’t mean they are ready to act.”

“It’s extremely unpredictable,” said Tatiana Stanovaya of the R. Politik consultancy.

Putin’s regime is built on mutual benefit, patronage and complicity, with oligarchs and regional leaders given license to loot the state in return for their loyalty. If they step out of line, they can be ruined overnight.

It is a repressive, highly adaptive regime with many tools to control the population. Putin has surrounded himself with yes men (there are few women) and clownish thugs, who pose no threat.

“It’s much better for him to be surrounded by these courtiers who are all mediocrities and who all hate each other than it is to have a really great group of people who are the best of their kind and can act independently,” said Andrew S. Weiss of the Carnegie Endowment for International Peace. “The more people are dependent on him, the more powerful he thinks he is, but at times like this, it obviously makes the system completely dysfunctional.”

This makes it difficult for anyone to try to remove Putin. The risk to him could heighten, however, if the self-interested, opportunistic elite begin to view him as a threat to their wealth and power.

“If enough people went to Putin and said that it’s time to go and, of course, his property would be guaranteed and his personal immunity would be guaranteed, the whole point of it would, of course, be to preserve the regime,” said Anatol Lieven of the Quincy Institute for Responsible Statecraft, a think tank. “But what if Putin refuses to go and then obviously takes revenge?” Lieven said. “That’s the biggest obstacle.”

Some argue that a successor, probably blaming Putin for the war, would have to be a centrist acceptable to the elite, who could end the war and build bridges to the West. In that frame, Sobyanin, the Moscow mayor, comes up a lot. A technocrat known for managing the coronavirus pandemic and rebuilding the capital for the 2018 soccer World Cup, he has quietly avoided cheerleading the war.

Anther low-key prospect, Dmitry Kozak, 63, the Kremlin deputy chief of staff, is a loyalist who worked with Putin in St. Petersburg in the 1990s. As Putin’s Ukraine envoy, he reportedly brokered a deal for Kyiv to drop its NATO aspirations around the time of the Feb. 24 invasion, but Putin rejected it. The Kremlin denied the deal, which was reported by Reuters last month.

Patrushev, the agriculture minister, who turns 45 next week, would represent generational change. “He could be made PM in one day and the next day he could be president,” said a person who once was close to Patrushev’s father and spoke on the condition of anonymity to comment on sensitive matters. “He speaks several languages. He’s young, and he didn’t take part in the war.”

A more likely Putin favorite might be his ex-bodyguard Alexei Dyumin, now governor of the Tula region. Dyumin led Russia’s special operations force, oversaw the seizure of Crimea in 2014 and served as deputy defense minister.

Then there is Medvedev, who was Putin’s stand-in president from 2008 to 2012. Once a liberal technology buff touring Silicon Valley, he is now a harsh nationalist, often threatening nuclear attack.

“I hate them,” Medvedev said in August. “They are bastards and degenerates. They want us, Russia, to die, and as long as I am alive, I will do everything to make them disappear.” He did not say if “they” were Westerners, Ukrainians or both. Despite the rhetoric, critics deride him as more pathetic than scary.

The recent attacks on Russian military commanders by Kadyrov, Prigozhin and others may be indicative of a jostling for money and prestige rather than power. “All of these characters kind of hate each other and are duking it out or trying to outmaneuver each other to get more of the spoils of the state,” Weiss said.

Kadyrov and Prigozhin are thuggish, ambitious and crafty, each with forces of several thousand men fighting in Ukraine, and Putin needs them if he is to win the war. But analysts minimize their chances. Kadyrov, who rules Chechnya as a fief, would be unacceptable to the elite. “Prigozhin does not have power base,” Galeotti said. He also discounted Nikolai Patrushev as tied too closely to Putin’s failures.

One name that never makes the list: Alexei Navalny, 46, the nation’s most prominent opposition leader, who might win in free elections but is in prison on trumped up charges. Navalny also is an enemy of the elite, unlike Dmitry Patrushev.

“Patrushev is from the system,” his father’s onetime associate said. “If he says ‘our position is the following and I have half the Federation Council and Duma behind me, let’s announce elections,’ he is speaking from a position of state. Navalny only speaks as a person from the street.”

The prospect of Russia’s elite acting against Putin seems remote, but Russia has a history of disorderly regime change, as in 1917 and 1991. “If you get a public split in the regime and the losing faction appealing to the streets,” Lieven said, “that is the moment when revolution, I mean mass popular unrest, really does become possible.”

The Washington Post’s Catherine Belton in London contributed to this report.

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