Ilmar Raag: Zelenskyy's real mistake and what it teaches us

Paradoxically, Ukrainian President Volodymyr Zelenskyy may indeed be guilty of not preparing adequately for war. But that is hindsight. Now, we face a greater problem than Zelenskyy's pre-war indecision, writes Ilmar Raag.
Volodymyr Zelenskyy has twice unequivocally acted as a hero. The first time was when he refused to leave Kyiv at the start of the war, and the second was now, at the White House, when he managed to remain true to himself under pressure from Donald Trump and JD Vance. We could see how uncomfortable he was. At one point, he crossed his arms defensively over his chest before forcing them back down. He was stunned and tense.
Yet Zelenskyy has also had his real failures, which tell a third story — one that neither side in the Oval Office mentioned. U.S. intelligence agencies are aware of this story, which makes Trump's hypocrisy even greater. It is the story of failed Russia deterrence.
In the spring of 2021, Ukrainian special forces neutralized a Russian GRU reconnaissance and sabotage group on Ukrainian-controlled territory in Donetsk Oblast. The equipment they carried and the intelligence they had gathered indicated that this was reconnaissance conducted in preparation for a larger operation.
By at least the fall of 2021, Ukraine's HUR intelligence agency had also confirmed that the Russians had launched a multi-phase planning and battlefield-shaping operation. This was recently reaffirmed in public by Kyrylo Budanov, head of Ukraine's military intelligence.
At the same time, a schizophrenic situation developed at the political level in Ukraine. Zelenskyy's team chose a public strategy of reassurance and occasional suppression of information, even as they privately expressed growing concern over the Russian troop buildup. The combat readiness of the armed forces was not increased, but various units and branches of the military made independent decisions. For instance, Ukrainian special forces began preparing teams to remain behind enemy lines.
It is possible that Zelenskyy's strategy was influenced by the stance of Western allies, who, until the very last moment, engaged in shuttle diplomacy with Moscow and urged Ukraine to avoid provoking the Kremlin. A crucial moment for Zelenskyy was his meeting with Joe Biden on September 1-2, 2021, where he tried to secure a U.S. commitment to NATO membership. However, Biden maintained his position that Ukraine's accession to NATO was not on the agenda. His primary aim was simply to express opposition to potential Russian aggression.
As the only concrete outcome of their meeting, Biden announced $60 million in military aid to Ukraine, which, given current war expenditures, was a minuscule sum — but it did include Javelins. Shortly thereafter, nearly every prominent Western leader called Vladimir Putin and on November 5, 2021, then-CIA Director William Burns also visited Moscow.
Thus, Zelenskyy saw that the West was attempting to take action, even though by December 2021, both Western and Ukrainian intelligence understood that war would begin within the next few months and that Russia had not been deterred.
From this point onward, decisions were made that Ukraine's military continues to criticize Zelenskyy for. First, in January 2022, Zelenskyy reallocated defense budget funds to road construction. That same month, British intelligence reported that the FSB had recruited Ukrainians to organize unrest under the guise of nationalist symbolism. Ukraine's SBU security service managed to apprehend these men, yet the political leadership did not initiate a broader crisis response.
Instead, strange events took place. For instance, in Kherson, demining was conducted on roads leading to Crimea, even as Russian forces were visibly gathering on the other side of the border. Partially, this was due to Russian agents embedded in Ukraine's security and government institutions. On February 15, 2022, the Royal United Services Institute (RUSI) published a report suggesting that Ukraine's counterintelligence was not actively pursuing all known Russian agents, fearing that their exposure would be demoralizing for society. The developments in Kherson Oblast were directly influenced by Oleg Kulinich, a Russian agent who at the time was head of the SBU's Crimea division and was obstructing intelligence reports.
Yet not all problems were caused by traitors. In the Aidar volunteer battalion, soldiers recalled being stationed in Donetsk Oblast in February 2022, as they had been engaged in combat there since 2014. That month, their entire battalion received just two Javelin anti-tank missile launchers. That was the only Western military equipment they had at their disposal.
At the same time, a local military commissariat sent an inspector to ensure that under no circumstances would they fire at the Russians — not even in self-defense — because a higher command had ordered that provocations be avoided at all costs. Aidar's soldiers then used the Javelins as observation devices, utilizing their thermal imaging sights to track Russian tank movements. They reported their findings up the chain of command, but no response ever came.
On February 21, Ukrainian intelligence learned through its agents that Moscow had issued an attack order to units stationed near the Ukrainian border. The same information reached Ukraine's Western allies, including Estonia. Yet, no widespread alarm was raised in Ukraine to "prevent panic." Again, different military branches made independent decisions, but inconsistently, as there was no unified political directive to begin resistance.
Many Ukrainian soldiers now believe that even within three days, much could have been done to strengthen defensive positions for future battles. The failure to act was primarily a political one — by Zelenskyy's administration.
Time was running out. On February 23, the Russian attack order reached rank-and-file troops. That same day, Ukrainian intelligence services also learned of it. Yet no nationwide alert was issued in Ukraine. As a result, some units in Kherson Oblast only learned that the war had begun when Russian forces crossed the border on February 24. Some territorial defense units (the equivalent of a national guard) were also only formed on the first day of the war.
By then, it was too late to establish an effective defense. It was also too late to deter the Russians. Had Zelenskyy been able to raise the combat readiness of the armed forces and announce at least reserve training exercises in January-February 2022, forming additional units, the Kremlin might have realized that its war plan — with a 180,000-strong invasion force — would not work.
Instead, the political leadership under Zelenskyy gave the impression that Ukraine was not actually preparing for resistance. And on this issue, there will be very serious questions for him to answer after the war.
This story illustrates that Ukraine truly did a lot to prevent war. Paradoxically, however, Zelenskyy may indeed be guilty of not preparing for war sufficiently. But that is hindsight. Now, we face a greater problem than Zelenskyy's pre-war indecision. Let us not repeat Ukraine's mistakes.
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Editor: Marcus Turovski