History often turns on one fatal error: underestimating the enemy. More than 2,500 years ago, Chinese military strategist Sun Tzu warned in The Art of War that victory depends on understanding both oneself and one’s adversary. His famous line — “If you know the enemy and know yourself, you need not fear the result of a hundred battles” — remains a timeless principle of strategy.
As modern conflicts unfold, this ancient warning appears increasingly relevant.
Russia’s Ukraine Gamble: A Case Study in Miscalculation
When Vladimir Putin launched a full-scale invasion of Ukraine in 2022, Moscow reportedly expected a rapid collapse of Kyiv’s leadership. Early reports suggested Russian forces even carried ceremonial uniforms, anticipating swift victory celebrations. Instead, the war has entered its fifth year, draining Russian resources and reshaping global geopolitics.
Analysts like Mykola Bielieskov of the Atlantic Council have argued that the Kremlin misjudged Ukrainian morale and adaptability. Rather than collapsing, Ukraine mobilised its population, strengthened its defence production, and embraced asymmetric warfare.
Similarly, commentator Crispin Hull in The Canberra Times noted that even Western intelligence underestimated Ukraine’s capacity for resistance. The assumption that technological superiority guarantees quick success proved dangerously flawed.
Strategic Resilience and Limits of Air Power
The war also exposed the limits of infrastructure warfare. According to the Institute for the Study of War (ISW), Russia’s missile and drone campaigns failed to cripple Ukraine’s energy grid or break civilian resolve. Instead, Ukraine reportedly expanded its defence industrial capacity dramatically, demonstrating how societies under threat can adapt faster than expected.
Russia’s later shift to targeting water systems suggested a tacit admission that earlier strikes had not achieved strategic objectives. The lesson is stark: destruction of infrastructure does not automatically translate into political collapse.
Is the US Underestimating Iran?
These precedents have sparked debate over Washington’s posture toward Iran. Some analysts warn that assuming economic sanctions, military strikes, or technological dominance will quickly destabilise Tehran could echo earlier miscalculations seen in Ukraine.
Concerns also extend to political assumptions. Just as Putin dismissed Ukraine as fragile, critics argue that expecting internal unrest alone to topple Iran’s leadership may ignore the regime’s security apparatus and capacity to regroup.
Iranian officials have projected defiance. Ali Larijani recently asserted that Iran had strengthened its defences and addressed weaknesses in recent months, signalling preparedness rather than vulnerability.
The Cost of Ignoring Asymmetric Realities
Modern warfare increasingly favours resilience, decentralised defence production, and societal willpower over sheer technological dominance. The Ukraine conflict underscores that morale and adaptability can offset conventional disadvantages.
If major powers ignore these realities, they risk repeating the very mistakes they once criticised in others. From Kyiv to Tehran, the central lesson remains unchanged since Sun Tzu’s era: misreading an adversary’s resolve can transform a planned swift campaign into a prolonged and costly struggle.
