Key Points – Ukraine’s audacious “Operation Spiderweb” drone strike over the weekend, reportedly destroying 41 Russian aircraft, including strategic bombers deep within Russia, has drawn praise from retired US military commanders.
-Lt. Gen. Mark Hertling lauded Ukraine’s ingenuity and resilience, while Adm. James Stavridis likened the tactic—involving drones launched from concealed sites inside Russia—to a modern “Trojan Horse.”
-While this “Pearl Harbor” style attack, years in planning and executed solely by Ukraine, dealt a significant blow to Russian assets and morale, it also carries the risk of severe Russian retaliation against Ukrainian civilian infrastructure as peace talks loom.
Retired US Commanders React to Ukraine’s ‘Pearl Harbor’ Attack on Russia
In what many are calling Russia’s “Pearl Harbor,” Ukraine launched a bold and meticulously coordinated drone strike deep inside Russian territory over the weekend, targeting key military airfields and destroying a reported 41 aircraft, including nuclear-capable bombers.
The audacious assault, reportedly orchestrated by Ukraine’s Security Service (SBU), involved deploying drones from concealed launch sites within Russian territory. According to Ukrainian sources, these makeshift launch pads, consisting of wooden sheds outfitted with retractable roofs, enabled its drones to evade detection and strike at the heart of Russia’s strategic air power.
The operation, years in the planning, was Ukraine’s longest-range attack to date, causing an estimated $7 billion in damage and impacting about a third of Russia’s cruise missile-carrying bombers.
Experts Praise Ukraine’s Resilience
Retired U.S. military leaders were quick to weigh in. Lieutenant General Mark Hertling, former commander of U.S. Army Europe, told Newsweek that the operation was evidence that Ukraine “has many aces in the hole.”
On social media, he credited Ukraine’s ingenuity and resilience, arguing that Kyiv’s forces have turned supposedly meager resources into sophisticated tools of asymmetric warfare. Retired Admiral James Stavridis, a former NATO Supreme Allied Commander, was even blunter: “Vlad is having a very bad day,” he quipped, adding that Ukraine’s tactics resembled a modern Trojan Horse.
The strategic implications are significant. Moscow has pushed hard on the ground in recent weeks, making incremental gains along Ukraine’s northeastern front. But this spate of drone strikes suggests Ukraine retains both the will and the capability to hit Russia where it hurts. For a war often depicted as grinding into stalemate, this operation is a reminder that Ukraine can still put the Kremlin on the back foot.
Predictably, Russia downplayed the damage. Its Ministry of Defense confirmed the drone attacks but claimed no casualties, a typical posture aimed at maintaining a façade of control.
Yet even Russian military bloggers, typically loyal to the regime, described the assault as a “Russian Pearl Harbor,” hinting at the scale of the psychological blow.
Attack Could ‘Come Back to Bite’ Kyiv
Ukrainian President Volodymyr Zelensky, celebrating the strike’s success, revealed that the operation took over a year and a half to prepare and was executed without foreign assistance. Ukraine is becoming increasingly willing to conduct of deep-penetration strikes.
Civilians at Risk
Although Moscow may be reeling right now, this attack could come back to bite Kyiv. What if Russia decides to retaliate more aggressively by striking civilian infrastructure, as it has done previously?
Even as Ukraine flexes its military creativity, diplomatic efforts continue. A fresh round of peace talks is scheduled to begin in Istanbul, but given the escalating stakes, hopes for a breakthrough remain dim.
In this high-stakes chess match, Kyiv’s latest gambit has not only embarrassed Putin but may have shifted the board itself. Whether it accelerates an end to the war or merely provokes further escalation remains to be seen.
About the Author:
Georgia Gilholy is a journalist based in the United Kingdom who has been published in Newsweek, The Times of Israel, and the Spectator. Gilholy writes about international politics, culture, and education.
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Zhduny
June 2, 2025 at 1:33 pm
True, the surprise attack on the airbases resembles the sneak attack on pearl harbor but the two have several differences.
In December 1941, the US was still expecting more negotiations with japan, like today where Russia and Ukraine are holding ongoing talks.
But in 1941, US was led by FDR, who was keen for US to enter ww2 but wanted japan to fire the first overt shot.
Today, in 2025, Russia is already one foot in the European ww3, but still largely half-asleep.
Today, in 2025, Russia has nuclear blunderbusters, unlike in 1941, where the US military was still not any bigger or stronger than Japan’s extremely experienced banzai force.
After the pearl strike, FDR spoke of the great American resolve, of pursuing the fight against Japan until through to achieving absolute victory.
But Putin ?
Putin likely thinks the Ukrainian attack is just a storm in a teacup. The losses aren’t his, they belong to the Russian people. Who cares.
Putin is no FDR and no longer a leader worth his salt. He needs to go.
Russia has only a short time before another person replaces donald trump as US president.
When that moment arrives, Russia could well find itself fighting USA directly, not just the Ukrainian fascists.
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