CNN
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December 31, 1999: Russian President Boris Yeltsin made a surprise radio announcement that he would tell his compatriots that he was resigning so that his prime minister could take over as president.

“Why hold on to power for another six months when the country has a strong leader who can be its president, a man on whom almost all Russians pin their hopes for the future?” Yeltsin said, acknowledging the pain of the collapse of the Soviet Union inflicted on ordinary Russians. “Why stand in his way?”

This strong leader was a political unknown: a former KGB officer named Vladimir Putin. When Putin addresses Russians this New Year’s Eve, he will celebrate a quarter of a century as Russia’s first man, both as president and, during a four-year interregnum, as powerful prime minister.

As 2024 draws to a close, Putin’s grip on power seems more certain than ever. On the battlefield in Ukraine, Russian forces have made progress in a grueling war of attrition and advanced into the Donbass region. At home, Russia’s political landscape has been stripped of competition following the death of the country’s most prominent opposition leader, Alexei Navalny.

And a month after Navalny died in a remote prison north of the Arctic Circle, the Kremlin leader sailed to re-election in a race that allowed him to win an overwhelming mandate, be damned.

Although Putin exudes confidence, new uncertainty is just around the corner. US President-elect Donald Trump promised during his election campaign to end Russia’s war against Ukraine. And while his roadmap to a negotiated solution to the conflict is far from obvious, Trump has made one thing clear: He wants it to happen quickly.

“(It’s) one of the things I want to do, and do quickly – and President Putin said he wants to meet with me as quickly as possible,” Trump said at a recent event in Arizona. “So we have to wait for it. But we have to end this war.”

No wonder there weren’t any champagne corks popping in Moscow after Trump’s re-election. Putin has staked everything on the war in Ukraine: he has put his country’s economy on a war footing; forged closer alliances with North Korea and Iran to keep the war machine running; and ended up on the International Criminal Court’s wanted list, all in pursuit of the maximalist goal of destroying Ukraine’s viability as a state.

Of course, Trump and Putin have some things in common. The Helsinki summit between the two in 2018 showed that Trump was willing to shatter long-established norms in foreign policy, just as Putin is, and Trump’s stated admiration for Putin’s strongman character is easing fears of authoritarianism among U.S. observers trends in our own country. But Trump’s capricious approach to foreign policy means the Kremlin may have to prepare for unpredictable negotiations.

Trump’s incoming special envoy to Russia and Ukraine, retired Army Gen. Keith Kellogg, has likened the war to a “cage fight” between the two countries that Trump can direct.

“You have two fighters and they both want to be eliminated, you need a referee to somehow separate them,” he said on Fox Business. “I think President Donald J. Trump can do that… I think he’s actually gotten both sides to come together – at some point – and talk.”

How this analogy will work in practice is an open question. Ukrainian President Volodymyr Zelensky has changed his rhetoric in recent weeks, conceding that Ukraine does not have the strength to regain all the territory lost to Russia. And Putin also signaled his willingness to negotiate in his question-and-answer session at the end of the year: “Politics is the art of compromise.” We have always said that we are willing to both negotiate and compromise.”

But beyond platitudes, Putin offered few details — and spent most of his televised year-end question-and-answer marathon trying to illustrate a position of strength to both ordinary Russians and the new Trump administration.

The Kremlin leader, for example, pushed back against a question from NBC’s Keir Simmons, who asked whether embarrassing foreign policy setbacks like the overthrow of the regime of Syrian President Bashar al-Assad, who recently sought refuge in Russia, meant he would step out negotiate from a position of weakness.

Putin’s response was: “We came to Syria ten years ago to prevent the emergence of a terrorist enclave like we have seen in some other countries, for example Afghanistan. We have largely achieved this goal.”

Despite the collapse of the Assad regime, Russia still has some diplomatic influence in the Middle East.

Hanna Notte, director of the Eurasia program at the James Martin Center for Nonproliferation Studies, a nonprofit U.S. nonproliferation study, said Russia still has “negotiating advantages” over Syria, including Moscow’s status as a permanent member of the Security Council United Nations.

“Russia’s role in the UN Security Council – where it can either exercise its veto or not – is important for HTS (Syria’s de facto ruler Hayat Tahrir Al-Sham) when it comes to all kinds of processes related to legitimation “Syrian government,” she said. “Any kind of process now that relates to a political transition in a post-Assad era, when the United Nations is involved, then I don’t think you want the Russians to be on the wrong side.”

Putin also sticks to positive talking points on the economic front, even as ordinary Russians feel the pain of high food prices and a falling ruble. But spin can only go so far. In a recent analysis, Alexandra Prokopenko, a fellow at the Carnegie Russia Eurasia Center, a Berlin-based think tank, found that Russia’s overstimulated war economy may be nearing a crisis point.

“With each passing month the pressure increases,” she wrote. “The Kremlin is approaching a tipping point where the social contract between the state and the people will inevitably shift. Russians are increasingly being asked to accept increasing inequality and a decline in quality of life in return for short-term stability and symbolic pride in the idea of ​​a “fortress nation.” But even this compromise is becoming less and less sustainable.”

Putin came to power 25 years ago with the promise of strong rule, after a decade of collective trauma during the Yeltsin era. He and his country must now face Trump in a new time of difficulty.