Zelensky: The Unlikely Leader Navigating Ukraine’s War

Zelensky: From Comedian to Wartime President

When Russian tanks crossed the border in February 2022, rumors swirled that Volodymyr Zelensky had fled Ukraine. Kyiv faced heavy bombardment, and European leaders braced for the worst. Then, the Ukrainian leader posted a grainy video – a defiant image of himself standing firm in front of the presidential building, flanked by his advisors, declaring simply: “We are here.”

A Target of Russia’s Plan

Zelensky’s removal was central to Russia’s swift takeover plan for Ukraine – a plan Moscow anticipated completing in days. He was to be captured or killed, or forced to flee. Sources revealed that Russian agents had even rented apartments near the presidential office with orders to eliminate him.

Defiance and Humor in the Face of Adversity

Early in the war, a joke circulated that Zelensky’s background as a comedian – his pre-political career – meant he wasn’t afraid of bombing. This humor encapsulated the defiant spirit of Ukraine. The story goes that when offered evacuation by the US, Zelensky famously responded: “I need ammunition, not a ride.”

Four Years of Resilience

As Ukraine approaches the fourth anniversary of Russia’s full-scale invasion, Zelensky’s message remains unchanged. He has survived approximately a dozen assassination attempts and navigated a corruption scandal that led to the dismissal of a close advisor and two top government ministers.

Insights from Those Closest to Zelensky

CNN spoke with individuals close to Zelensky – including his wife and speechwriter – as well as European and US diplomats and politicians who have worked closely with him and his administration to assess his position.

A Leader in the Mold of Churchill?

Many attribute Zelensky’s staying power to his political skills and inspirational speeches, drawing comparisons to Winston Churchill. However, like Churchill, Zelensky has faced missteps, and his future is increasingly uncertain as the war continues. While 60% of Ukrainians trust him, only half believe he should seek a second term.

Navigating Domestic Challenges

Last July, Ukrainians protested government plans to weaken anti-corruption watchdogs, forcing Zelensky to reverse course. He also clashed with his popular former military chief, General Valerii Zaluzhnyi, ultimately dismissing him in 2024. He’s also had to manage a complex relationship with a US president who has publicly criticized him.

A Childhood Forged in Strength

Bartosz Cichocki, Poland’s ambassador to Kyiv during the invasion, believes Zelensky’s resilience stems from his childhood in Soviet Ukraine. “You had to prove your strength, particularly if you were a little Jewish boy trying to prove to everyone around that you deserve respect,” Cichocki explained. “He does not respect weakness, he can confront superior power… you need that when you have to confront people like Putin.”

An Unconventional Path to Leadership

At 48, Zelensky is the youngest person to lead an independent Ukraine and its most unlikely leader. A lawyer by training, he entered politics with no prior experience, having built a career in showbusiness. He rose to fame in the TV show “Servant of the People,” where he played a schoolteacher unexpectedly becoming president.

From Comedy to the Presidency

His presidential candidacy was initially dismissed as a joke, but he won over 73% of the vote, defeating incumbent Petro Poroshenko. Before politics, Zelensky built a successful business empire. Henry Hale, a professor at George Washington University, notes this experience prepared him for the top job, understanding the necessity of working with oligarchs who control Ukrainian media.

The Power of Direct Communication

Zelensky excels at direct communication, preferring video messages – an idea from his speechwriter, Dmytro Lytvyn. “He decided on the first day that he must explain to people what’s going on,” Lytvyn said. These informal, often selfie-style videos resonate deeply, especially with soldiers on the frontlines.

A Symbol of Ukrainian Identity

Zelensky speaks Ukrainian fluently, despite growing up speaking Russian. He dedicated himself to mastering the language as an adult, recognizing its importance to national identity.

A Defining Moment of Courage

Zelensky’s decision to remain in Kyiv as Russian forces advanced was a pivotal moment, demonstrating his leadership and earning the trust of many Ukrainians. His wife, Olena Zelenska, described the initial “acute fear” that later transformed into a constant, suppressed anxiety.

Facing Ongoing Challenges

Ukraine initially repelled the Russian attack on Kyiv and reclaimed territory. However, progress stalled after the liberation of Kherson in 2022. A failed counter-offensive in 2023 led to clashes with General Zaluzhnyi, and a stalemate persists along the 1,200-kilometer frontline. Peace negotiations remain stalled due to Russia’s uncompromising demands.

Seeking International Support

Zelensky understands Ukraine’s need for international assistance, particularly from the United States. His forceful appeals for help have yielded results, convincing initially reluctant nations like Germany to provide support.

A Difficult Relationship with Trump

However, his relationship with US President Donald Trump has been fraught with difficulty. Trump has accused Zelensky of being a dictator and questioned Ukraine’s role in the conflict. A disastrous meeting at the White House, where Trump and Vice President Vance accused Zelensky of not wanting peace, highlighted the challenges.

Adapting to a Complex Political Landscape

Despite the difficulties, Zelensky has reportedly found a way to communicate effectively with Trump, according to Senator Richard Blumenthal.

Maintaining Public Support

Despite fluctuations, Zelensky maintains a strong approval rating, never falling below 52%, according to KIIS polling data.

A Leader Connected to His People

Zelensky’s commitment to connecting with ordinary Ukrainians is evident in his impromptu meetings, like the one with Ukrainian cleaners in the Czech Parliament.

Facing Corruption Allegations

Recent corruption scandals have damaged Zelensky’s image, despite his promise to clean up politics. The dismissal of close allies, including Andriy Yermak, raised questions about his judgment.

The Weight of War

The years of pressure have taken a visible toll on Zelensky. He relies on coffee to navigate a demanding schedule, often starting between 3 a.m. and 4 a.m. His wife acknowledges the constant emotional strain.

Resilience and Determination

Despite the challenges, Zelensky remains determined. As one advisor put it, “He knows how to roll with the punches.”