In the early hours of June 1, 2025, Ukraine launched a bold, coordinated drone assault deep into Russian territory, dubbed Operation Spider’s Web. The targets were not tactical vehicles or frontline troops, but the core of Russia’s long-range strike capability. Ukrainian sources estimate that around 40 aircraft were destroyed or disabled, including Tu-95 and Tu-22M3 bombers, cornerstones of Moscow’s strategic air deterrent. Satellite imagery showed charred runways, cratered tarmacs, and entire hangars reduced to rubble. The operation reportedly cost Ukraine less than $2 million. The damage to Russia: potentially $7 billion, with some analysts estimating that 20 to 25 percent of its strategic bomber arsenal was eliminated in a single night.

It was one of the most audacious operations of the war. It was made possible because both President Volodymyr Zelensky and President Vladimir Putin command their militaries with near-total authority. Putin, as an autocrat, faces no democratic checks. Zelensky, while democratically elected, governs under martial law with centralized wartime powers. In this moment of existential conflict for Ukraine and high-stakes confrontation for Russia, both men are unbound by the usual constraints of democratic politics. Both possess the authority and the burden to make high-risk decisions that could reshape the trajectory of the war.

Zelensky’s decision to authorize this deep strike into Russian territory was one such decision. It was not just militarily significant. It was a signal, a strategic statement that Ukraine can reach the heart of Russian power on its own terms and with its own tools. It did not rely on NATO weapons or foreign advisors. It was Ukrainian-built, Ukrainian-planned, and Ukrainian-executed.

And it marked a turning point in the war’s political logic. Because more than anything else, this operation was an act of calculated brinkmanship.