Photo illustration: Eniola Odetunde. Photos via Mikhail Svetlov/Getty Images

Twenty years ago, on New Year's Eve 1999, a political newcomer and former KGB operative named Vladimir Putin suddenly assumed the Russian presidency.

Part two of our "20 Years of Putin" special report examines what he has built, and what will happen to it when he's gone. It's based on conversations with exiled oligarch Mikhail Khodorkovsky, three former U.S. ambassadors to Moscow, leading experts and former chiefs of the Pentagon and CIA. Read part one.

From stability to uncertainty

Vladimir Putin has contended — with a nod to the chaos swirling in the West and to Russia's tumultuous history — that the most precious thing a leader can offer his country is stability.

Why it matters: Putin has not made Russia rich, free or particularly happy. But he imposed stability and has maintained it for two decades through his own blend of force and skill. Putin's current term expires in 2024, and the constitution bars him from seeking another.

Zoom in: Dmitri Trenin, director of Carnegie Moscow and a former Russian military officer, does not believe Putin will change the constitution to become "president for life." Thus, he says, “2024 will be the last year that Vladimir Putin will be president of Russia."

  • "Everyone will see that this guy is not for the future, which means that his real power will wane," Trenin says. "So yes, his time is coming to a close."
  • Others disagree. "He will be in power as long as he can," says Mikhail Khodorkovsky, the oligarch infamously jailed by Putin in 2003. "The methods he can use will vary, but he will be very keen to stay in power as long as he’s alive."

Two specific methods have been floated, beyond a constitutional change:

1. Putin forms a commonwealth with Belarus, maintaining presidencies in both countries but placing himself above them.

  • Some in Belarus fear the groundwork is being laid through Russian propaganda, and Belarusian strongman Alexander Lukashenko is due to meet Putin on Saturday to discuss bilateral ties — though he insisted this morning that Belarusian sovereignty is sacrosanct, per Reuters.

2. Putin builds himself another powerful role — like chair of the National Security Council — and oversees a staged transition from that perch.

  • That path was paved by Kazakhstan's Nursultan Nazarbayev, who began to bring his three decades in power to a carefully choreographed close in March.

Where things stand: Putin will be 71 when his term expires. He told the FT in June that he had been thinking about succession "since 2000."

  • But he has no obvious heir, and as longtime diplomat and Russia expert Daniel Fried puts it: “If you break down institutions, every succession is a crisis.”
Expand chart
Data: Gleditsc and Chiozza, 2016, "Archigos — A Data Set on Leaders 1875–2015", Axios research; Note: Data through August, 2019; Chart: Chris Canipe/Axios

The big picture: The "mafia-esque structure" Putin has built requires loyalty within elite circles and support from the public, says Alina Polyakova of Brookings.

  • He has ensured that those with wealth or power "owe all of what they have to Putin himself," while masterfully controlling his public image.
  • “At this point, it’s impossible to distinguish between Putin the man and Putin the system," she says.
  • "There could be another head at the top, but that head would have to be just as good as Putin at managing all of these competing interests.”

Zoom out: The Russian system collapsed twice in the 20th century, in 1917 and 1989–1991.

  • In the century since the Russian Revolution, Trenin says, Putin's tenure does indeed stand out for its stability.
  • Now, he says, "We are facing a high degree of uncertainty in Russia."

The bottom line: "This transition will never be very smooth and will never be very happy even," says Trenin. But history will judge Putin on its outcome.

Putin behind the throne: The Medvedev years
"I choose you." Putin and Medvedev (R) in 2007. Photo: Dmitry Astakhov/AFP via Getty Images

Putin has left the Kremlin once before, when he first ran up against term limits in 2008 and became prime minister.

Behind the scenes: "We always had an assessment, perhaps exaggerated, that Putin was the main decision-maker and [Dmitry] Medvedev was just a figurehead," says Michael McFaul, who was Barack Obama's Russia adviser and later ambassador to Moscow.

  • As president, though, Medvedev was Obama's primary interlocutor. A few months in, McFaul suggested a call about the Olympics — Putin had just won Sochi 2014 — as a backdoor into direct dialogue.
  • “When Obama tried to pivot to Iran, Putin said, ‘Look, I’m not in charge of foreign policy, Medvedev is, but he happens to be sitting right here. I’ll hand over the phone.'"
  • "That was a real shot across the bow to us," McFaul recalls.

Flash forward: “We always thought Putin was coming back," McFaul continues, "but there was enough ambiguity that you could hold open the possibility that maybe Medvedev would stay.”

  • Rumor has it, McFaul says, that Medvedev didn't know his presidency was ending in 2012 until the day before Putin's announcement. "Whether that was all a big game for us, I can’t evaluate.”

The bottom line: “[Putin], like a lot of autocrats, convinced himself that he was the indispensable player and that Russia needed his strong hand in the Kremlin," says William Burns, who was then deputy secretary of state.

  • Many Russians disagreed, particularly the educated urbanites who took to the streets.
  • "I think he was surprised by the scope of the street protests," Burns says. "He immediately assumed that there had to be other hands behind this."
Putin and the West: Distrust and disruption
Putin meets with Hillary Clinton in 2010. He accused her of backing protests against him. Photo: Alexey Nikolsky/AFP via Getty Images

McFaul originally thought Putin was exaggerating both the threat to his regime during the 2012 protests and the role he attributed to the U.S.

  • That changed after he heard Putin express his suspicions behind closed doors with top U.S. officials.

Behind the scenes: “He had no incentive to tell [national security adviser] Tom Donilon or [Secretary of State] John Kerry that we’re trying to overthrow the regime. That’s supposed to be for the workers and the peasants. But in those conversations, I heard a level of suspicion — he just assigned all kinds of power to the United States and especially the CIA that they don’t have."

"I think psychologists would call it projection," Burns says, noting that Putin had suspicion drilled into him as a KGB officer.

  • Fear-mongering about the West is a political tool, allowing Putin to justify repression and economic stagnation at home.
  • At the same time, "he convinced himself that the way to create space for Russia as a major power is to chip away at the United States," Burns says.

Former Secretary of Defense Ash Carter is more blunt. "One of his objectives is to screw us. That, unlike Syria or nuclear proliferation, is not an area where I am willing to reach common ground."

  • As the leader of a "weakening power," Carter says, "being a spoiler and nuclear weapons are the things he has left."

The bottom line: "Declining powers in a lot of ways — as Putin reminded us — can be at least as disruptive as rising powers," says Burns.

Putin and Ukraine: Spheres of intervention

Putin issued that reminder in 2014 when he annexed Crimea and launched the war in eastern Ukraine.

The big picture: Putin views Ukraine as firmly within Russia's sphere of influence, and he saw Kiev's sudden shift toward the West as an existential threat.

Orthodox Christianity is a soft power tool for Putin in his geopolitical neighborhood. Photo: Mikhail Klimentyev\TASS via Getty Images
  • If Ukraine, a country Russians see as a sibling, takes a European path and living standards begin to rise, Fried asks, "what does that do to Putinism?”
  • "He wants to keep this bleeding wound open and try to hold Ukraine back," adds Alexander Vershbow, a former U.S. ambassador to Moscow. "But it’s not really working that way.”
  • While Putin's aggression may have driven Ukraine further away, it also put the West on notice.

Behind the scenes: “We didn’t have the resources devoted to Russia that we needed to understand what Russia was doing under Putin," says Michael Morell, a former CIA deputy director, noting that the invasions of Ukraine and of Georgia in 2008 took Washington utterly by surprise.

  • Morell, who served as George Bush's intelligence briefer, said Bush asked questions after the Georgia invasion that "we couldn’t answer" due to post-Cold War cutbacks and prioritization of the War on Terror.
  • It wasn't until Crimea that Washington's radar truly locked in on Moscow. Next came Putin's interventions in Syria and in the 2016 U.S. election.

The bottom line: Just a few years after being dismissed by Obama as a "regional power," Russia was being discussed in Washington as one of three key players in an era of "great power competition."

Russia and China: Growing apart, together

Two of those three powers inaugurated a 1,800-mile-long symbol of their burgeoning partnership yesterday.

Driving the news: The Power of Siberia pipeline will deliver Russian gas to China and is expected to “generate $400 billion for Russian state coffers,” per Reuters.

  • Putin hailed it as “a genuinely historical event” on a video link with Xi Jinping, with whom he has celebrated birthdays, flipped pancakes and struck notes of mutual admiration.
Drinking buddies, Xi (L) and Putin, in Shanghai. Photo: Sasha Mordovets/Getty Images

The big picture: Asked about the relationship with his giant neighbor, Putin told the FT, "We have sufficient eggs, but there are not too many baskets to put those eggs in."

Between the lines: He's squeezing everything he can out of a relationship that currently provides massive economic and strategic benefits, but is also increasingly imbalanced.

  • "The window of opportunity in which Russia has something to offer to China that China still wants is very narrow," says Polyakova. Beijing is also a powerful friend for a man who's been "kicked out of all the Western clubs."

The bottom line: “Right now it’s a pretty strong marriage of convenience," says Burns, "born of a shared interest in chipping away at an American-led order."

  • "There’s lots of tactical reasons to stay together, but I do think as you look out over the next five or 10 years, Russians are likely to be just as uncomfortable being the junior partner of China as they were being the junior partner of the United States.”
Exporting Putinism: 'Liberalism is over'

Putin looks at China's rise, Trump's election and Europe's identity crisis and reaches a provocative conclusion: "the liberal idea has become obsolete."

Why it matters: Putin's alternative path has been embraced by high-profile politicians and a widening slice of the European electorate:

  • "Let everyone be happy," he told the FT, bundling together migrants, minorities and LGBTQ people. "But this must not be allowed to overshadow the culture, traditions and traditional family values of millions of people making up the core population."
  • Outside Russia's borders, Putin's philosophy could be summed up as "live and let oppress." He scoffs at Western intervention in the name of freedom or human rights, citing Iraq and Libya as cautionary tales.

Zoom out: “Putinism is a new set of ideas that is exportable," McFaul says, noting the rise of Europe's far right. “He’s not alone in this fight.”

“I think he thinks he’s engaged in an ideological struggle. And by the way, he thinks he’s winning,” says McFaul.
Too big to fall: No returning to the shadows
Hail to the czar. Putin with Yeltsin at his inauguration in 2000. Photo: Laski Diffusion/Newsmakers

The little-known KGB veteran who thrived in the shadows, underestimated and overlooked, has grown into a giant.

He's not only one of the world's most powerful men, he may be one of the richest. Anders Åslund of the Atlantic Council pegs his net worth at $100 billion to $160 billion, including a $1 billion palace on the Black Sea.

  • In Putin's Russia, Trenin says, "corruption is not a bug in the system. Too often, it is the system itself."
  • As Khodorkovsky explains, everyone in the chain of command "must steal," with the full knowledge of their superiors, who can then use that information to control them. Step out of line and find yourself in prison — for stealing.

After 20 years at the top of that pyramid, with all the wealth and all the enemies he's accumulated along the way, leaving power would be perilous.

  • "There is no one who is able to guarantee him the kind of safety that he was able to guarantee to Boris Yeltsin," Polyakova contends.
  • "He’s got what I call the King Lear problem," says Fried. "How do you go into retirement comfortably after you’ve done the things King Lear has done? There’s a reason people are out to get you."
"Do you think Putin doesn’t know what he’s done?"

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