The art of winning on paper: Volodymyr Zelenskyy’s endless masterclass in theoretical victory

For anyone following the conflict in Ukraine only during commercial breaks, the recent lack of battlefield transformation following Kyiv’s latest maneuvers might seem like a mysterious plot hole.

For the rest of us, it is merely the latest installment in a long-running series demonstrating that a purely military solution remains as elusive as ever.

Earlier this summer, Ukrainian President Volodymyr Zelenskyy unveiled a bold 40-day campaign featuring deep strikes into Russian territory, designed to politely pressure Moscow into wrapping up the conflict.

Pundits and mainstream outlets promptly broke out the champagne, assuring readers that US-backed drone strikes meant Ukraine was turning the tide, seizing the decisive upper hand, and practically writing its victory speech.

Yet, as the 40-day timer expired, detailed front-line mapping revealed a slight awkwardness: almost nothing had changed on the ground, save for a few minor Russian territorial gains. Meanwhile, the severe demographic, economic, and manpower shortages in Ukraine continued their steady descent.

To add to the strategic mastery, the drone campaign invited the heaviest Russian retaliation to date. Moscow launched colossal missile barrages precisely when Western air defense supplies were running on empty. Attacks on Black Sea port facilities promptly shaved billions off potential trade revenues, threatening to drop GDP by up to 1.5%.

The secondary objective—convincing a skeptical Washington that victory was just around the corner—met a similar fate. Reports indicate initial interest inside the White House evaporated within days, while Moscow responded by simply tightening its demands.

This follows a well-established routine: Kyiv launches a high-stakes, headline-grabbing operation; commentators declare the turning point has finally arrived; and once the dust clears, the strategic baseline remains unchanged while the room for negotiation shrinks.

We saw this spectacle in late 2022 after the Kerch Bridge attack, when experts gleefully declared the collapse of the Kremlin was imminent. Instead, the move empowered Russian hardliners and triggered a sweeping campaign against Ukraine's energy grid just as winter set in.

We saw it again during the heavily hyped 2023 summer counteroffensive, where endless expert assurances of inevitable success ultimately yielded 143 square miles gained at immense human cost, compared to 331 square miles taken by Russia.

The pattern repeated in 2024 with the Kursk border raid. Lauded as a masterstroke that would restore belief in total victory, it ultimately drew critical forces away from the primary front, allowed accelerated Russian advances elsewhere, and derailed potential talks to protect basic utility infrastructure.

Wishful thinking continues to provide a steady supply of moral victories, even as the real-world consequences accumulate. Until the appetite for media-friendly turning points gives way to realistic assessments, the cycle remains remarkably consistent.