Updated February 24, 2022 at 3:51 PM ET
Ukrainian President Volodymyr Zelenskyy has found himself leading a country at war after Russia's invasion started late Wednesday night. It's a marked change for a man who less than three years ago was best known for his work as an actor, comedian and entertainment executive.
Before his election, Zelenskyy starred in a TV show called Servant Of the People, where he played an outsider turned president. It was a ratings hit, but winning the actual presidency was quite unexpected, said Joshua Yaffa, the Moscow correspondent for The New Yorker.
"Essentially, he was the beneficiary of disillusionment and frustration that had built up in Ukraine by 2019 as a result both of the war in Donbas, which remained unsettled, [and] also the unchecked role of the oligarchs," Yaffa said. "Again, it was clear the Ukrainian people were desperate for an alternative – any alternative — and Zelenskyy showed up on the political scene and benefited from his lack of experience, frankly."
Russia's invasion of Ukraine is certainly the greatest challenge Zelenskyy has faced as president to date, but Yaffa said at the beginning of his term the main challenge was navigating the complexities of being a president to a real-life country rather than a TV show that he created.
"So his presidency was marked by a certain messiness and difficulty that I'm not sure Zelenskyy and his associates quite understood – that all of the kind of trickiness and complexity that goes into actually running a country," Yaffa said.
One early challenge was an offer of quid pro quo from former U.S. President Donald Trump, where he offered U.S. military aid in exchange for cooperation on a political investigation.
"It was turned out to be much more difficult, or maybe, in fact, Zelenskyy didn't have all the will required to undo the country's system of oligarchs, corruption, favor trading," Yaffa said.
That interaction with Trump has continued to have an effect on Zelenskyy's relationship with the U.S., Yaffa said, including his approach to messaging ahead of Russia's invasion. At times, the Ukrainian president took issue with the urgency and imminency shared in messages from the U.S. about the incoming invasion.
"On the one hand, he has a lot of different issues to worry about here — yes, of course, first and foremost, the prospects of a Russian invasion. But in the meantime, he's watching foreign embassies flee Kyiv, expat workers, investors flee the country," Yaffa said. "The notion at this point of new foreign investment, I think, is all but frozen."
It's all part of an ongoing headache for Zelenskyy, Yaffa said.
"It's proven difficult, if not impossible, for him to square the circle between Putin, the West, domestic factions inside Ukraine," he said. "And, of course, a big reason why Zelenskyy has not been able to end this war is Vladimir Putin."
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