Kyiv, Ukraine – It’s nearly impossible to picture Volodymyr Zelenskyy clean-shaven, dressed in casual clothes, and cracking jokes right next to the Kremlin.
“I’m here, in the heart of Russia – if it still has a heart,” a radiant Zelenskyy quipped in a satirical “news dispatch” filmed near the Kremlin’s red walls.
The year was 2014. Moscow had already annexed Crimea and was backing separatists in Donbas, as well as pro-Kremlin protesters in Ukraine’s Russian-speaking east and south.
At the time, Zelenskyy was a comedian, actor, and head of the District 95 troupe. For him, politics was material for sarcastic routines. “You can say, ‘hail Ukraine’ in Moscow, and nothing serious will happen to you,” he said in the video. “Nothing that can’t be handled by modern medicine.”
More than a decade later, Zelenskyy no longer cracks jokes for a living. Instead, he is the president of wartime Ukraine – and on Friday, he is scheduled to meet with US President Donald Trump in Washington.
Three years after Russia launched its full-scale invasion of Ukraine, Zelenskyy’s nation needs more than modern medicine to survive. Trump has signaled a willingness to sacrifice Kyiv’s interests for a deal with Russian President Vladimir Putin, whom he has previously praised.
Last week, Zelenskyy stunned the world by offering to resign in exchange for security guarantees and NATO membership for Ukraine. This comes amid growing personal tensions with Trump, who has ruled out Kyiv’s entry into the alliance.
But surprising people is nothing new for Zelenskyy.
His political brand, since entering politics, has been built on the idea that he’s not a typical politician, eager to cling to power at any cost. Zelenskyy’s carefully curated, ever-shifting image has been central to that narrative.
‘Ukraine of my dreams’
Since the late 1990s, Zelenskyy the actor has worn a dizzying array of masks on stage and screen.
He performed in front of Russian President Vladimir Putin, impersonated Putin’s alleged mistress Alina Kabayeva, wore black latex and high heels while lamenting the taste of uncured lard, and played Napoleon, musketeer d’Artagnan, and a wannabe heartthrob in slapstick comedies and TV series.
And, of course, there was his role as Vasily Holoborodko, a dirt-poor history teacher whose obscene rant about corrupt politicians and oligarchs in the series Servant of the People made Zelenskyy a YouTube star and propelled him to the presidency.
This marked Zelenskyy’s first image makeover.
Ukrainians had grown disillusioned with Petro Poroshenko, an oligarch-turned-president who reneged on his pledges to end the Donbas war and quell corruption when he came to power in 2014 – and instead became mired in his own corruption scandals.
In 2018, Zelenskyy registered a political party aptly named Servant of the People – and topped opinion polls months before officially entering the election race. A psychologist explained his decision to become a politician as reflective of his “trickster” desire to upend Ukraine’s political order.
“Zelenskyy is an archetypal trickster, a person who destroys, despises, doubts things, breaks the rules,” psychologist Valentyn Kim told the DSNews.ua website in June 2022. He “stormed into Ukrainian politics as a destroyer of previous political accords.”
And during war, a trickster is “a more effective figure” than traditional leaders, Kim added.
During his election campaign, Zelenskyy’s public relations team shrewdly streamlined his media coverage by avoiding press conferences and interviews with foreign media. Instead, they controlled the narrative through videos and social media posts.
He announced his candidacy on New Year’s Eve, a secular holiday in much of the former Soviet Union – and congratulated Ukrainians with a “new public servant”: himself.
He began wearing suits and turtlenecks, and his pledges sounded youthfully optimistic.
“I’ll tell you about the Ukraine of my dreams. The Ukraine where the only shooting is the sound of wedding fireworks, the Ukraine where you can register a business in an hour, get a passport in 15 minutes, and vote in one second, online,” he said in a booklet distributed by his team in early 2019.
In the April 2019 presidential election, he trounced Poroshenko, winning a staggering 73 percent of the vote – the highest ever in Ukrainian history.
Zelenskyy was the anti-establishment golden boy, the peacenik who celebrated his election in a nightclub and promised to rewrite Ukraine’s political playbook.
As he took the presidential oath, Zelenskyy came across as someone who was “anti-power, destined to do things differently, not the way his predecessors did,” Svitlana Chunikhina, vice president of the Kyiv-based Association of Political Psychologists, told Al Jazeera.
Rising Amid Anti-Semitism
In most of his comedic roles, Zelenskyy spoke Russian – often with an exaggerated accent, a cliché typically associated with Ukrainian Jews. It was an artistic nod to the Black Sea port of Odesa, the capital of Ukraine’s Jewish community and satire.
But Zelenskyy himself is Jewish. His great-grandfather and three of his sons were killed by German Nazis. The only surviving child, Semyon, was a decorated World War II hero.
Today’s Ukraine lionizes Semyon’s sworn enemies – nationalist, anti-communist, and anti-Semitic leaders Stepan Bandera and Roman Shukhevych – turning a blind eye to their collaboration with the Nazis and their role in the mass killings of Jews and Poles.
Given that czarist-era Ukraine was the epicenter of pogroms that drove millions of Ashkenazi Jews to the United States and Palestine, Zelenskyy’s rise to power seems even more improbable.
Surprisingly, his roots “were not part of the agenda” during the 2019 campaign, Kyiv-based analyst Vyacheslav Likhachyov told Al Jazeera.
Zelenskyy’s “turbo-patriotic opponents had enough triggers,” such as District 95’s irreverent jokes about anti-Russian protesters who clashed with police loyal to pro-Kremlin President Viktor Yanukovych, and about a decree from the Constantinople Patriarch Bartholomew on establishing a new Ukrainian Orthodox Church independent from the Moscow Patriarchate.
However, there were widespread insinuations from Poroshenko loyalists and nationalist groups that Zelenskyy was a puppet of Jewish Ukrainian oligarch Ihor Kolomoisky, whose 1+1 television network aired District 95 shows and the Servant of the People series.
Proving the insinuations wrong took four years – Kolomoisky was arrested in 2023 and charged with organizing the killing of a lawyer two decades earlier. The arrest became part of Zelenskyy’s half-hearted campaign to rein in oligarchs who used their clout and media empires to back politicians.
Zelenskyy’s Jewish roots, however, never stopped pro-Kremlin media from labeling him a “neo-Nazi” whose “fascist junta” hired far-right goons and foreign “mercenaries” to “suppress” Ukraine’s alleged political tilt toward Moscow.
A New Reality
Zelenskyy’s promise to bring new people to power and end the Donbas war with Russian proxies won him support – and the presidency.
“He was absolutely sincere in trying to negotiate peace” with Putin, Volodymyr Fesenko, head of the Kyiv-based Penta think tank, told Al Jazeera. It wasn’t, he said, a case of “populist lies.”
The Servant of the People party quickly recruited a motley crew of B-list politicians, rookies, and anti-corruption activists – and won 227 seats in Ukraine’s 450-seat parliament in July 2019.
“This is indeed a new reality,” Kyiv-based analyst Mikhail Pogrebinsky told Al Jazeera after the vote.
The party gained a monopoly on forming a new government, appointing regional heads, and controlling the judiciary and law enforcement.
Some insiders were sceptical.
“This is going to be a disaster for Ukraine,” a showbusiness executive who knew Zelenskyy and his team told Al Jazeera on condition of anonymity days before the vote. “In their field [of comedy] they’re good professionals, but I don’t think these people know what they’re doing in politics.”
From Ukraine’s ‘Mars’ to the Presidential Palace
Many of Zelenskyy’s closest allies hailed from his hometown – Kryvyi Rih (“Crooked Horn”), a rustbelt city in central Ukraine with a pre-war population of 630,000.
Resembling a 120km (75-mile) long inkblot, it’s filled with mines, smelters, and steel plants, surrounded by mountains of spent ore and potholed roads.
Locals affectionately compare it to Mars due to iron ore dust and industrial pollution that reddens the air, birds’ plumage, and even snow.
Kryvyi Rih’s residents are known for their toughness, straightforwardness, and down-to-earth nature.
“This is a city of steely, manly character that never lets one down – the character of camaraderie and mutual support,” historian and tour guide Volodymir Kazakov told Al Jazeera days before Zelenskyy’s 2019 election.
Zelenskyy grew up in a relatively prosperous family of university professors in a part of town he would make famous with his comedy group: District 95.
Still, this reporter saw broken vodka bottles and obscene graffiti on the staircase leading to his parents’ apartment on the 12th floor of a Soviet-era concrete building. Zelenskyy was born there in 1978, and neighbors described him as a natural leader.
“He was a bright and busy boy,” Tatyana Oreshaka, a housewife in her 50s, told Al Jazeera. “If other kids had an argument, they’d ask him to be a judge.”
Zelenskyy grew up during the 1990s, a chaotic decade marked by economic transition, poverty, heroin abuse, and organized crime. Kryvyi Rih shaped Zelenskyy’s “iron-fisted business acumen” and reliance on childhood friends, Kazakov said.
Thirty members of Zelenskyy’s District 95 group or its associates became part of his government, according to the Committee of Voters of Ukraine, a civil group.
One of them is lawyer Andriy Yermak, head of the presidential administration, widely seen as Zelenskyy’s “grey cardinal.” Another is Ivan Bakanov, who made a fortune in hydroelectric power before leading District 95 and the Servant of the People party.
In 2019, Zelenskyy appointed Bakanov to head the Security Service of Ukraine – but fired him three years later after a string of scandals involving Russian spies and corruption allegations.
A dozen more firings and corruption scandals in the party have further tarnished Zelenskyy’s image.
“Members [of the party] very quickly began showing a propensity for corruption,” analyst Fesenko said. “And Zelenskyy didn’t have a solution.”
‘Ukraine’s Churchill’
Most importantly, Zelenskyy’s attempts to pacify Putin failed.
The turning point was 2021, when Zelenskyy lost “his naive belief that he could deal with Putin,” Fesenko said.
Zelenskyy resisted Moscow’s pressure, sanctioning oligarch Viktor Medvedchuk, Putin’s ally in Ukraine, and shutting down his media empire, which promoted pro-Kremlin narratives.
Meanwhile, Putin declared Ukraine “an artificial state” and amassed tens of thousands of troops, launching an invasion on February 24, 2022.
It was time for Zelenskyy’s biggest transformation.
Contrary to US President Joe Biden’s advice to flee, he stayed in Kyiv – even as Russian forces seized northern suburbs, killing hundreds of civilians, and bombarded the city with missiles.
The one-time jester became a David fighting the Russian Goliath.
“No one expected Zelenskyy to become a wartime leader, a Ukrainian Churchill,” Fesenko said. “He made the existential choice on the war’s first day – win or die.”
Zelenskyy’s new look – green military fatigues, a week-old stubble, and an air of weary determination – accompanied this transformation.
He relentlessly toured Western capitals, delivering speeches in his limited English and urging military and financial aid.
Zelenskyy still occasionally cracked jokes, sometimes lost in translation.
His approval ratings soared, especially after Russian forces withdrew from Kyiv, northern Ukraine, the Kharkiv region, and the southern city of Kherson.
Western leaders like Biden and then-British Prime Minister Boris Johnson saw their visits to Kyiv as a badge of honor and a boost to their approval ratings.
Zelenskyy began to embrace his political and personal power.
“These days, he is power. He doesn’t live the role but feels fully comfortable within it,” psychologist Chunikhina said. “He’s still not against doing things differently, but he doesn’t shun power as something inherently alien.”
However, though US President Donald Trump described Zelenskyy as a “dictator” with a 4 percent approval rating last week, the Ukrainian leader remains widely popular. Amid his spat with Trump, Zelenskyy’s ratings have actually jumped from 58 to about 65 percent, according to a February 21 survey.
Zelenskyy’s grip on power, experts say, is nothing like Putin’s – at least not yet.
“The risk of merging with the job is dangerous to any politician in any circumstances,” Chunikhina said.
Emerging Rival: Zaluzhnyi
Yet to many in Ukraine, Zelenskyy is also increasingly a symbol of the country’s military struggles. The 2023 and 2024 counteroffensives failed to bring a victory, as US military aid stalled for months – largely due to Trump’s pressure on Republican members of Congress to withhold funding for Kyiv.
Meanwhile, Russia continues to advance in Donbas despite heavy losses. Critics argue that Zelenskyy-appointed regional heads failed to build impregnable fortifications, spending billions of dollars on paper.
Many blame Zelenskyy for the February 2024 firing of his top commander, Valerii Zaluzhny, a taciturn four-star general now serving as Ukraine’s ambassador to the UK.
Borislav Bereza, a former legislator with the nationalist UKROP party, claimed in a video that Zelenskyy’s team may file criminal charges against Zaluzhnyi for allegedly ordering the removal of landmines between annexed Crimea and the Kherson region days before the invasion.
In Zaluzhnyi, Zelenskyy may have found his nemesis and main political rival.
Three-quarters of Ukrainians trust Zaluzhnyi, seeing him as a reliable father figure and ideal protector.
Like Zelenskyy in 2018, Zaluzhnyi has never said a word about running for president – but is widely expected to contest the election whenever it is held.
“If Zaluzhnyi takes part in the [presidential] vote, Zelenskyy loses,” Fesenko said.
Other political heavyweights, such as former President Poroshenko and former Prime Minister Yulia Tymoshenko, are also expected to compete in a future presidential election.
But observers warn that any new president will face challenges very different from those Zelenskyy confronted when he first took office six years ago.
Millions of Ukrainians have been uprooted, their hometowns destroyed. Ukraine needs billions to rebuild housing and infrastructure, while a dire demographic crisis may thwart hopes of full recovery.
Zelenskyy’s offer to resign might not have been only a tactical ploy.
“The presidential chair these days is an electric chair,” Kyiv-based analyst Oleh Saakyan said in televised remarks on February 20. “No one wants to get there to immediately absorb all the negative stuff.”
For the latest updates and more news, visit ZTC News and ZNews Today.