Is Ukraine’s 'Spider's Web' attack Russia’s Pearl Harbour moment? What happened on Dec 7, 1941 and the next day

Ukraine’s “Spider Web” drone strike has sent shockwaves through Russia’s military establishment. On the night of June 1, 2025, Ukraine launched one of the deepest and most ambitious operations of the war so far—targeting strategic airbases thousands of kilometers inside Russian territory. Using over a hundred low-cost FPV drones, the operation destroyed or damaged more than 40 military aircraft, including nuclear-capable bombers.

While the physical damage is staggering, what has captivated global attention is the psychological impact: for the first time since the war began, Russia’s supposedly secure heartland was penetrated with devastating precision.

Some military commentators are now likening the operation to a modern-day “Pearl Harbour” - not in scale of bloodshed, but in shock value and potential to shift the course of war.

Operation ‘Spider Web’: Ukraine strategic drone assault

Ukraine's Security Service (SBU) meticulously planned Operation "Spider Web" over 18 months, aiming to cripple Russia's long-range aerial capabilities. Utilizing 117 low-cost, first-person-view (FPV) drones, Ukraine targeted four Russian airbases located thousands of kilometres from its borders, including sites in Siberia. The drones were covertly transported into Russia, concealed within trucks, and launched from disguised containers, catching Russian defences off guard.

The attack resulted in the destruction or damage of key Russian military aircraft, including Tu-95 and Tu-22M3 bombers, as well as A-50 reconnaissance planes. These aircraft have been instrumental in Russia's aerial operations against Ukraine. The estimated financial impact of the strike is around $7 billion, significantly degrading Russia's strategic bombing capabilities.

Pearl Harbour: A historical parallel

The comparison to Pearl Harbour stems from the surprise nature and strategic impact of Ukraine's drone attack. On December 7, 1941, the Japanese Imperial Navy launched a surprise military strike against the United States naval base at Pearl Harbour, Hawaii, resulting in significant losses and leading to the U.S. entering World War II. The attack involved over 350 aircraft and caused the destruction of numerous ships and aircraft, as well as over 2,400 American casualties.

While Ukraine's drone assault did not result in immediate loss of life, its strategic implications are profound. By penetrating deep into Russian territory and targeting critical military assets, Ukraine demonstrated its capability to strike with precision and surprise, challenging Russia's sense of security within its own borders.

However, Sergej Sumlenny, an expert on Eastern Europe and the founder of the European Resilience Initiative Center, has opined against the comparison.

In an X post, Sumlenny wrote: “Stop calling it Pearl Habor. Pearl Harbour: 1) was an unprovoked act of aggression, 2) had no strategic importance; 3) led to attacker's defeat. This is more the Battle of Yavin, if you need a comparison: a destruction of aggressor's weapon of unpunished terror by a small force.”

Stop calling it Pearl Habor. Pearl Harbour:1) was an unprovoked act of aggression,2) had no strategic importance;3) led to attacker's defeat.This is more the Battle of Yavin, if you need a comparison: a destruction of aggressor's weapon of unpunished terror by a small force. pic.twitter.com/XQJJ1f5a8b
Sergej Sumlenny, LL.M (@sumlenny) June 1, 2025

What happened at Pearl Harbour

On the morning of January 7, 1941, the Japanese Imperial Navy launched a surprise aerial attack on the US naval base at Pearl Harbour, Hawaii. The attack lasted for less than two hours but inflicted catastrophic damage on the US Pacific Fleet. Over 350 Japanese aircraft, launched from six aircraft carriers, bombarded battleships, cruisers, airfields, and support installations.

The consequences were immediate and severe: more than 2,400 Americans were killed, including military personnel and civilians, and eight battleships were either sunk or severely damaged—among them the USS Arizona and USS Oklahoma. Over 300 aircraft were damaged or destroyed.

Pearl Harbor is remembered not only for its human and material toll but for the strategic implications. Japan had hoped the shock-and-awe tactic would demoralize the United States and forestall its entry into World War II, giving Japan time to consolidate its control over the Pacific. However, the attack had the opposite effect.

What happened after Pearl Harbour

On December 8, 1941 – the day after the attack – President Franklin D Roosevelt addressed a joint session of the Congress in what became one of the most iconic speeches in American history. Referring to the attack as “a date which will live in infamy,” Roosevelt asked for – and received – a formal declaration of war against Japan. Just three days later, Germany and Italy declared war on the United States, and the U.S. reciprocated, fully entering World War II.

Rather than knocking the U.S. out of the Pacific, Pearl Harbor provoked a total war response that ultimately led to Japan’s defeat and the end of World War II in 1945, following the atomic bombings of Hiroshima and Nagasaki.