On December 31, 1999, Russian President Boris Yeltsin made a surprising announcement to the Russian public. He revealed that he would step down and hand over power to his prime minister, a relatively unknown figure at the time.

"Why should I cling to power for another six months when the country already has a leader capable of guiding us forward? A man whom most Russians are hopeful about for the future?" Yeltsin said, acknowledging the difficulties the country faced after the collapse of the Soviet Union. This strong leader was Vladimir Putin, a former KGB officer. This New Year's Eve marks 25 years of Putin's rule, a period in which he has served both as president and, during a brief interlude, as prime minister.

As 2024 draws to a close, Putin's grip on power appears unshakeable. On the war front, Russian troops continue to make slow but steady gains in Ukraine, especially in the Donbas region. Domestically, the political scene has become devoid of any substantial opposition following the death of the prominent dissident Alexei Navalny. The Russian leader also won re-election with an overwhelming margin, despite the questions surrounding the fairness of the process.

While Putin projects confidence, there is fresh uncertainty looming, brought on by the return of Donald Trump to the political stage. The former U.S. president campaigned on a promise to end the war in Ukraine, and although the specifics of his plan remain unclear, he has made it clear that he intends to bring about a swift resolution to the conflict.

Trump’s stance is a potential problem for Putin. The Russian president has staked much of his political future on the war, shifting Russia’s economy to a wartime footing, building alliances with nations like North Korea and Iran, and facing international consequences such as being wanted by the International Criminal Court. For Putin, the aim has been to undermine Ukraine’s status as a viable state.

Despite their differences, Trump and Putin have shared interests. Their 2018 summit in Helsinki showed that Trump was willing to challenge traditional diplomatic norms, just as Putin has done throughout his rule. Trump’s admiration for Putin's strongman image also raised concerns about authoritarian tendencies in the U.S. However, Trump’s unpredictable foreign policy style may present challenges for the Kremlin, requiring them to prepare for a possible negotiation that could be less structured than expected.

Keith Kellogg, Trump’s appointed envoy to handle Russia and Ukraine, has described the situation as a “cage fight” between the two nations, with Trump in the role of the referee.

The question remains: how will this "cage fight" play out? Recently, Ukrainian President Volodymyr Zelensky shifted his rhetoric, acknowledging that Ukraine may not be able to reclaim all the territory it lost to Russia. Meanwhile, Putin also expressed openness to negotiation, even though he avoided offering specifics. He reiterated his stance that politics is about compromise, signaling that Russia is ready for talks, but the details remain elusive.

Putin’s rhetoric in his recent year-end address mostly projected strength. When asked about Russia’s setbacks in Syria, he argued that Russia had achieved its goal of preventing the rise of terrorist strongholds, underscoring that the country still retains some diplomatic leverage in the Middle East, particularly through its position on the UN Security Council.

At home, Putin’s messages about Russia’s economy have been positive, despite the pain felt by ordinary citizens who are facing rising food prices and a devaluing ruble. However, experts warn that Russia’s wartime economy is heading toward a crisis. Alexandra, a fellow at the Carnegie Russia Eurasia Center, noted that growing inequality and a declining quality of life could cause social unrest, especially as the government asks its people to accept these sacrifices for short-term stability.

When Putin first rose to power 25 years ago, he promised to restore order after a decade of turmoil during Yeltsin's presidency. Now, he faces new challenges, with Donald Trump potentially altering the course of Russia’s war in Ukraine and the political landscape at home shifting under the strain of prolonged conflict. The next chapter of Putin’s rule is about to unfold, and it remains to be seen how he will navigate this new challenge.