Five years after the Maidan revolution ousted a corrupt pro-Russian president amid fervent hopes of national resurgence, the Ukrainian people have voted overwhelmingly to oust their first Maidan-anointed leader, incumbent President Petro Poroshenko. In his place they have elected a former television star, Volodymyr Zelensky, Ukraine’s first Jewish president and the only current Jewish world leader outside of Israel.For all that is known about the very public figure, the character of the man who is now the commander in chief of tens of thousands of Ukrainian servicemen and women engaged in a simmering low intensity conflict with their larger neighbor, Russia, remains opaque. Zelensky is an enigmatic figure who gave almost no interviews to Ukrainian journalists while he was running for office, eschewed most mainstream media, and did not announce the majority of his positions or team until almost a week before the second round of the election. As it happens, Tablet readers enjoy a special insight into the mind and character of the elusive new leader of Ukraine, not only as a matter of religious kinship but through, yours truly. I was the rare journalist able to spend a long stretch of time with Zelensky. As a result, dozens of people from the Ukrainian political class (including the representatives of major oligarchs) have contacted me to inquire after my impressions of his character and personality. Previously, I had been circumspect, preferring to keep some insights to myself, but now I will tell you what I know about the Ukrainian Jew who is poised to become the country’s next president.The 41-year-old Zelensky, a former comedian and actor, had been known for playing an ordinary man of the people turned accidental president on his hit television show Servant of the People. After Sunday’s election he will enter office to serve his people with a titanic mandate. With exit polls showing Zelensky having won a landslide 73% of the vote, the results of the election were not only decisive but also a stinging humiliation for the sitting president. The incumbent Poroshenko, it appears, had both radically underestimated the level of satisfaction with Ukrainian elites, and despite some substantive and respectable achievements in the foreign policy sphere, also arguably squandered a historic opportunity to be remembered as a father of his nation. Poroshenko had run a campaign highlighting his formidable stewardship of Ukraine’s international affairs, his role in the creation of an independent Ukrainian church, and his success in making Ukrainian the official language of the country’s education system. None of which seemed to satisfy an electorate more concerned with continued corruption in a country where many have difficulty making ends meet and paying utility bills despite an economy growing at 3%. It is a testament both to the depth of dissatisfaction with the ruling elites among average Ukrainians, and the relative paucity of credible candidates, that Zelensky the TV president is now the actual president.As an official international observer for the elections, I had a front-row view of the process. One of my colleagues on my Odessa-based team, a fellow Ukrainian American, observed that the election results were “the biggest and most unambiguous blowout in the history of Eastern European political life since the collapse of the Soviet Union.” The judgment was as astute as it was grandiose. The depth of the resentment that President Poroshenko engendered in the region of his birth (Odessa, where Zelensky scored 85%) and his political home region of Vinnitsa (where Zelensky scored 70%) was striking, with the precinct I observed handing 10 votes to the amateur upstart comedian for every one it gave the man who had negotiated the Minsk accords. President Poroshenko graciously conceded his defeat shortly after polls had closed and with that, Ukraine showed a peaceful transition of power that served as an example to post-Soviet societies from Central Asia to the border of the Baltics.Yet, this is not to say that no one inside Ukraine has been shaken up by the election results. It is clear that Zelensky emulated U.S. President Donald Trump, in his deft command of social media and nonconventional modes of campaigning. And it appears very likely that, like Trump, Zelensky had run a spoiler presidential campaign with no expectation of victory and perhaps never having expected to get as far as he did. It is in fact more likely that he had thought that he would do well and afterward would pick up several dozen seats in the October parliamentary elections. It would not be surprising if despite his bravado he were as terrified as anyone would be to find himself the victor of the elections.As has been widely and gleefully repeated by Ukrainian patriots, Zelensky’s election paves the way for Ukraine to be the only state other than Israel to have concurrently a serving Jewish president and Jewish prime minister (Volodymyr Groysman). If nothing else, Sunday’s electoral results should finally shatter the five-year-long Kremlin narrative of Kiev having been captured by a neo-Nazi fascist junta. Still, in private, multiple leaders of the Ukrainian Jewish community expressed worry to me about that situation not being an appealing one for the Jewish community in the long term if Zelensky fails as a political leader. However, as I told Ha’aretz, Zelensky forcefully defended the history and contributions of Ukrainian Jews to the country when we met the day before the first round of voting. His political designs appear to be fairly conventional manifestations of populism: mainstreaming of rule by referendums along with tax amnesties and stripping MPs of legal immunity. It is as a campaigner that Zelensky showed a propensity for radical innovations, and set a new precedent for political tomfoolery that will likely be copied in future elections the world over.Ukraine’s new president is the son of a Jewish intelligentsia family from Krivyi Rih, a gritty industrial city in the country’s Russian-speaking South. The symbolic location of his birthplace has served to reassure some voters that he would respect a truce between mutually hostile Russian-leaning and Ukrainian-nationalist visions of the country’s cultural future. His humor is based in vaudevillian slapstick and is fairly rough, owing far more to the aesthetic of late ’80s Soviet sketch comedy than to a modern sensibility, such that he has been criticized for occasionally trafficking in Russian stereotypes about provincial Ukrainians.Much of the commentary in the Western press about Ukraine’s East-West and language divisions has been fatuous and misinformed. Yet, promoters of aggressive Ukrainization of their nation’s cultural and educational spheres are not wrong in seeing that Zelensky’s election represents at least a temporary halt to those ambitions. Zelensky’s campaign had cannily avoided taking substantive positions on those sort of divisive questions, allowing him to remain a blank screen (an unavoidable pun) onto which different segments of the population could project their fantasies. As evidence of his success at appealing to different groups within the country: The only demographic that Zelensky lost was Ukrainians living abroad.In person he is fairly slight in height, intense, charismatic and in possession of a muscular upper torso that tells the story of daily bouts of heavy weightlifting, which along with a penchant for a working-class tinged bravado and a quick temper point to a high-strung personality. Many political professionals in Ukraine speculated that the Zelensky campaign refused to take part in traditional television-studio-aired debates for the reason that they did not want to see Zelensky be placed side by side with the much taller and thicker-set president. In any case Zelensky came off as the more masculine of the two during the debate.Any serious candidate in Ukrainian presidential politics depends on the backing of an oligarch for funding and media access, and, in this case, the country’s first Jewish president has enjoyed the backing of the picaresque and archly villainous, Ihor Kolomoyskyi, a Ukrainian Jewish billionaire and media magnate who has been living in Israel after fleeing his native country amidst an ongoing court case involving charges of financial fraud. It’s clear that Kolomoyskyi backed Zelensky’s campaign with money, television, and the usage of at least some of his close aides, but the pivotal question now is just how much influence the oligarch will be allowed to wield over the new president’s administration. Crucially, it remains to be seen whether Kolomoyskyi will be able to place his preferred candidate in the critical role of the head of the presidential administration.For the new Zelensky administration, the choice might be between picking a neophyte untainted by contact with the political establishment, and thus impeccably free of any taint of corruption, and sacrificing some of their reformist cred to get an experienced pair of hands wielding the institutional machinery—someone, that is, like Kolomoyskyi’s preferred candidate, former Odessa Governor Igor Palitsa. In fact Zelensky’s team may not have a choice, even if they would prefer to sideline the oligarch, who in the final days of the campaign announced he would be returning to the country from his exile in Israel after a Zelensky victory.While comparisons to Trump may obscure as much they illuminate, Zelensky faces many of the same risks and challenges that have defined the American president’s first term.Many of the people around Zelensky, much like in the case of Trump, have a business or entertainment background. There will be childhood friends and close associates who will ask for favors and sinecures. Also like Trump, Zelensky will have difficulty quickly assembling a team and forming political cadres. Again, a lack of understanding and experience with the policy process and leverages of power may cause the same sort of chaotic first year in office that plagued the Trump administration. The difference is that Ukraine’s personalized politics and lack of strong institutions ensure that a weak or incompetent president will always create infinitely more problems and risks than a similar figure would provoke in a more robustly developed democracy. Yet, my own personal impressions of Zelensky as a shrewd, bright, and educable leader, make me think that he will be a much tougher political infighter than his critics expect him to be. The task before him will be tremendous, even before his having to build a party from scratch to contest the upcoming parliamentary elections.The campaign having concluded, Zelensky is now set to face off against an intransigent parliament, a belligerent and resourceful Russian foe, scheming oligarchs, and the tremendous expectations of viewers watching at home. Whether he will be able to fashion himself into a Ukrainian Macron—or at least the idealized Macron that the French leader’s supporters had imagined him to be—able to assuage the aspirations and dreams of Ukrainians who have already watched him save the country on their television sets, or will go down in history as a much more conventional Ukrainian political figure, is the topic of next season’s plot line.***Like this article? Sign up for our Daily Digest to get Tablet magazine’s new content in your inbox each morning.