Trump’s Instinctive War Strategy Unravels Against Iran’s Resilience

President Donald Trump’s defence approach against Iran is unravelling, exposing a fundamental failure to understand past lessons about the unpredictable nature of warfare. A month after US and Israeli aircraft launched strikes against Iran after the killing of Supreme Leader Ayatollah Ali Khamenei, the Iranian regime has demonstrated surprising durability, continuing to function and launch a counteroffensive. Trump appears to have miscalculated, apparently expecting Iran to crumble as rapidly as Venezuela’s regime did after the January capture of President Nicolás Maduro. Instead, faced with an adversary far more entrenched and strategically sophisticated than he anticipated, Trump now confronts a difficult decision: reach a negotiated agreement, claim a pyrrhic victory, or escalate the conflict further.

The Failure of Quick Victory Prospects

Trump’s critical error in judgement appears rooted in a problematic blending of two entirely different geopolitical situations. The quick displacement of Nicolás Maduro from Venezuela in January, accompanied by the establishment of a US-aligned successor, created a false template in the President’s mind. He ostensibly assumed Iran would fall with equivalent swiftness and finality. However, Venezuela’s government was economically hollowed out, torn apart by internal divisions, and possessed insufficient structural complexity of Iran’s theocratic state. The Iranian regime, by contrast, has survived decades of worldwide exclusion, trade restrictions, and internal pressures. Its defence establishment remains intact, its ideological underpinnings run extensive, and its leadership structure proved more durable than Trump anticipated.

The failure to distinguish between these vastly distinct contexts reveals a troubling trend in Trump’s approach to military planning: depending on instinct rather than thorough analysis. Where Eisenhower stressed the critical importance of thorough planning—not to predict the future, but to establish the conceptual structure necessary for adapting when reality diverges from expectations—Trump seems to have skipped this foundational work. His team presumed swift governmental breakdown based on surface-level similarities, leaving no backup plans for a scenario where Iran’s government would continue functioning and fighting back. This absence of strategic planning now puts the administration with few alternatives and no obvious route forward.

• Iran’s government remains functional despite the death of its Supreme Leader
• Venezuelan economic crisis offers flawed template for Iranian situation
• Theocratic system of governance proves significantly resilient than anticipated
• Trump administration is without contingency plans for extended warfare

The Military Past’s Lessons Go Unheeded

The chronicles of military affairs are filled with warning stories of military figures who overlooked basic principles about military conflict, yet Trump looks set to add his name to that unenviable catalogue. Prussian strategist Helmuth von Moltke the Elder noted in 1871 that “no plan survives first contact with the enemy”—a principle born from painful lessons that has remained relevant across different eras and wars. More in plain terms, boxer Mike Tyson expressed the same truth: “Everyone has a plan until they get hit.” These observations go beyond their historical context because they embody an immutable aspect of combat: the adversary has agency and can respond in manners that undermine even the most carefully constructed plans. Trump’s government, in its conviction that Iran would rapidly yield, appears to have disregarded these perennial admonitions as immaterial to modern conflict.

The repercussions of disregarding these insights are currently emerging in the present moment. Rather than the swift breakdown anticipated, Iran’s regime has demonstrated institutional resilience and operational capability. The demise of paramount leader Ayatollah Ali Khamenei, whilst a considerable loss, has not triggered the political collapse that American planners ostensibly expected. Instead, Tehran’s security apparatus remains operational, and the leadership is mounting resistance against American and Israeli combat actions. This development should surprise nobody versed in historical warfare, where countless cases illustrate that removing top leadership infrequently generates swift surrender. The lack of contingency planning for this entirely foreseeable eventuality reflects a core deficiency in strategic planning at the highest levels of state administration.

Eisenhower’s Overlooked Insights

Dwight D. Eisenhower, the American general who commanded the D-Day landings in 1944 and later held two terms as a GOP chief executive, offered perhaps the most incisive insight into strategic military operations. His 1957 remark—”plans are worthless, but planning is everything”—emerged from direct experience overseeing history’s most extensive amphibious campaign. Eisenhower was not dismissing the importance of strategic objectives; rather, he was highlighting that the real worth of planning lies not in creating plans that will stay static, but in cultivating the intellectual discipline and flexibility to respond intelligently when circumstances inevitably diverge from expectations. The planning process itself, he argued, immersed military leaders in the nature and intricacies of problems they might face, enabling them to adapt when the unexpected occurred.

Eisenhower elaborated on this principle with typical precision: when an unforeseen emergency arises, “the initial step is to take all the plans off the top shelf and throw them out the window and start once more. But if you haven’t engaged in planning you can’t start to work, intelligently at least.” This difference separates strategic capability from simple improvisation. Trump’s government seems to have skipped the foundational planning entirely, rendering it unprepared to adapt when Iran failed to collapse as anticipated. Without that intellectual groundwork, decision-makers now face choices—whether to claim a pyrrhic victory or increase pressure—without the structure necessary for sound decision-making.

Iran’s Strategic Advantages in Asymmetric Conflict

Iran’s resilience in the wake of American and Israeli air strikes demonstrates strategic strengths that Washington appears to have underestimated. Unlike Venezuela, where a largely isolated regime fell apart when its leaders were removed, Iran possesses deep institutional structures, a sophisticated military apparatus, and decades of experience functioning under international sanctions and military strain. The Islamic Republic has developed a network of proxy forces throughout the Middle East, created backup command systems, and developed asymmetric warfare capabilities that do not depend on traditional military dominance. These elements have enabled the state to absorb the initial strikes and remain operational, demonstrating that targeted elimination approaches rarely succeed against states with institutionalised power structures and dispersed authority networks.

Moreover, Iran’s regional geography and regional influence provide it with strategic advantage that Venezuela did not possess. The country sits astride critical global energy routes, wields significant influence over Iraq, Syria, and Lebanon via affiliated armed groups, and operates sophisticated cyber and drone capabilities. Trump’s assumption that Iran would concede as quickly as Maduro’s government reveals a basic misunderstanding of the regional balance of power and the endurance of institutional states versus personalised autocracies. The Iranian regime, whilst undoubtedly weakened by the assassination of Ayatollah Khamenei, has exhibited organisational stability and the means to align efforts across various conflict zones, suggesting that American planners fundamentally miscalculated both the intended focus and the likely outcome of their opening military strike.

• Iran maintains proxy forces across Iraq, Syria, Lebanon, and Yemen, impeding immediate military action.
• Advanced air defence networks and dispersed operational networks reduce the impact of aerial bombardment.
• Digital warfare capabilities and unmanned aerial systems offer unconventional tactical responses against American and Israeli targets.
• Control of Strait of Hormuz shipping lanes provides commercial pressure over worldwide petroleum markets.
• Institutionalised governance prevents against governmental disintegration despite loss of highest authority.

The Strait of Hormuz as a Strategic Deterrent

The Strait of Hormuz serves as perhaps Iran’s strongest strategic position in any extended confrontation with the United States and Israel. Through this narrow waterway, approximately roughly one-third of international maritime oil trade passes annually, making it one of the most essential chokepoints for international commerce. Iran has regularly declared its intention to shut down or constrain movement through the strait were American military pressure to escalate, a threat that possesses real significance given the country’s defence capacity and geographic position. Obstruction of vessel passage through the strait would promptly cascade through global energy markets, pushing crude prices significantly upward and placing economic strain on friendly states that depend on Middle Eastern petroleum supplies.

This economic constraint substantially restricts Trump’s options for further intervention. Unlike Venezuela, where American involvement faced limited international economic consequences, military escalation against Iran threatens to unleash a worldwide energy emergency that would damage the American economy and damage ties with European allies and fellow trading nations. The prospect of strait closure thus functions as a powerful deterrent against continued American military intervention, giving Iran with a degree of strategic advantage that conventional military capabilities alone cannot provide. This situation appears to have eluded the calculations of Trump’s military advisors, who went ahead with air strikes without properly considering the economic repercussions of Iranian retaliation.

Netanyahu’s Clarity Versus Trump’s Improvisation

Whilst Trump seems to have stumbled into military confrontation with Iran through instinct and optimism, Israeli Prime Minister Benjamin Netanyahu has pursued a far more calculated and methodical strategy. Netanyahu’s approach reflects decades of Israeli defence strategy emphasising continuous pressure, incremental escalation, and the preservation of strategic ambiguity. Unlike Trump’s seeming conviction that a single decisive strike would crumble Iran’s regime—a miscalculation rooted in the Venezuela precedent—Netanyahu recognises that Iran represents a fundamentally distinct opponent. Israel has invested years developing intelligence networks, creating military capabilities, and building international coalitions specifically designed to contain Iranian regional power. This measured, long-term perspective stands in sharp contrast to Trump’s preference for dramatic, headline-grabbing military action that offers quick resolution.

The divide between Netanyahu’s strategic clarity and Trump’s improvisational approach has generated tensions within the armed conflict itself. Netanyahu’s government appears focused on a prolonged containment strategy, prepared for years of reduced-intensity operations and strategic rivalry with Iran. Trump, by contrast, seems to anticipate swift surrender and has already begun searching for exit strategies that would enable him to announce triumph and turn attention to other priorities. This fundamental mismatch in strategic outlook threatens the unity of US-Israeli military cooperation. Netanyahu is unable to follow Trump’s lead towards early resolution, as taking this course would render Israel vulnerable to Iranian retaliation and regional competitors. The Israeli leader’s organisational experience and institutional memory of regional conflicts give him advantages that Trump’s transactional, short-term thinking cannot match.

The lack of coherent planning between Washington and Jerusalem produces significant risks. Should Trump advance a negotiated settlement with Iran whilst Netanyahu stays focused on military action, the alliance risks breaking apart at a pivotal time. Conversely, if Netanyahu’s commitment to ongoing military action pulls Trump deeper into heightened conflict with his instincts, the American president may end up trapped in a sustained military engagement that contradicts his stated preference for swift military victories. Neither scenario serves the enduring interests of either nation, yet both continue to be viable given the core strategic misalignment between Trump’s improvisational approach and Netanyahu’s institutional clarity.

The Global Economic Stakes

The escalating conflict between the United States, Israel and Iran threatens to destabilise global energy markets and derail tentative economic improvement across multiple regions. Oil prices have started to vary significantly as traders expect likely disturbances to sea passages through the Strait of Hormuz, through which approximately 20 per cent of the world’s petroleum passes daily. A prolonged war could provoke an energy crisis similar to the 1970s, with cascading effects on rising costs, monetary stability and market confidence. European allies, facing economic pressures, face particular vulnerability to supply shocks and the risk of being drawn into a conflict that threatens their geopolitical independence.

Beyond concerns about energy, the conflict endangers global trading systems and financial stability. Iran’s likely reaction could strike at merchant vessels, interfere with telecom systems and spark investor exodus from developing economies as investors seek secure assets. The erratic nature of Trump’s policy choices compounds these risks, as markets struggle to account for possibilities where American decisions could swing significantly based on political impulse rather than strategic calculation. International firms working throughout the Middle East face escalating coverage expenses, distribution network problems and geopolitical risk premiums that ultimately filter down to customers around the world through elevated pricing and diminished expansion.

• Oil price volatility undermines worldwide price increases and central bank effectiveness at controlling interest rate decisions effectively.
• Insurance and shipping expenses rise as maritime insurers require higher fees for Persian Gulf operations and cross-border shipping.
• Investment uncertainty prompts capital withdrawal from developing economies, intensifying currency crises and sovereign debt challenges.