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

President Donald Trump’s military strategy against Iran is falling apart, exposing a fundamental failure to learn from past lessons about the unpredictability of warfare. A month following US and Israeli warplanes launched strikes against Iran after the killing of Supreme Leader Ayatollah Ali Khamenei, the Iranian regime has shown unexpected resilience, continuing to function and mount a counter-attack. Trump appears to have misjudged, seemingly anticipating Iran to collapse as rapidly as Venezuela’s government did following the January capture of President Nicolás Maduro. Instead, faced with an opponent far more entrenched and strategically sophisticated than he anticipated, Trump now faces a difficult decision: negotiate a settlement, declare a hollow victory, or intensify the conflict further.

The Collapse of Quick Victory Expectations

Trump’s tactical misjudgement appears stemming from a dangerous conflation of two entirely different regional circumstances. The swift removal of Nicolás Maduro from Venezuela in January, accompanied by the placement of a US-aligned successor, established a misleading precedent in the President’s mind. He apparently thought Iran would fall with equivalent swiftness and finality. However, Venezuela’s government was financially depleted, divided politically, and possessed insufficient structural complexity of Iran’s theocratic state. The Iranian regime, by contrast, has weathered extended years of worldwide exclusion, financial penalties, and internal pressures. Its defence establishment remains functional, its ideological underpinnings run extensive, and its governance framework proved more durable than Trump anticipated.

The inability to distinguish between these vastly different contexts exposes a troubling pattern in Trump’s strategy for military planning: depending on instinct rather than thorough analysis. Where Eisenhower emphasised 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 appears to have skipped this foundational work. His team assumed 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 limited options and no obvious route forward.

• Iran’s government keeps functioning despite losing its Supreme Leader
• Venezuelan collapse offers inaccurate template for Iranian situation
• Theocratic political framework proves considerably resilient than expected
• Trump administration lacks backup strategies for sustained hostilities

Armed Forces History’s Lessons Go Unheeded

The chronicles of military affairs are filled with warning stories of leaders who disregarded basic principles about combat, yet Trump seems intent to join that unfortunate roster. Prussian strategist Helmuth von Moltke the Elder observed in 1871 that “no plan survives first contact with the enemy”—a doctrine rooted in bitter experience that has proved enduring across different eras and wars. More colloquially, fighter Mike Tyson captured the same reality: “Everyone has a plan until they get hit.” These observations go beyond their historical context because they demonstrate an unchanging feature of combat: the enemy possesses agency and can respond in fashions that thwart even the most thoroughly designed strategies. Trump’s administration, in its conviction that Iran would rapidly yield, appears to have disregarded these enduring cautions as immaterial to contemporary warfare.

The ramifications of ignoring these precedents are currently emerging in real time. Rather than the quick deterioration expected, Iran’s government has demonstrated institutional resilience and functional capacity. The passing of Supreme Leader Ayatollah Ali Khamenei, whilst a considerable loss, has not precipitated the administrative disintegration that American strategists apparently envisioned. Instead, Tehran’s defence establishment remains operational, and the regime is actively fighting back against American and Israeli combat actions. This result should surprise any observer versed in military history, where many instances show that removing top leadership rarely results in quick submission. The failure to develop alternative strategies for this entirely foreseeable situation constitutes a critical breakdown in strategic planning at the uppermost ranks of state administration.

Ike’s Underappreciated Guidance

Dwight D. Eisenhower, the U.S. military commander who led the D-Day landings in 1944 and later held two terms as a GOP chief executive, provided perhaps the most incisive insight into military planning. His 1957 remark—”plans are worthless, but planning is everything”—stemmed from firsthand involvement overseeing history’s largest amphibious military operation. Eisenhower was not dismissing the importance of tactical goals; rather, he was emphasising that the true value of planning lies not in producing documents that will stay static, but in developing the mental rigour and adaptability to respond effectively when circumstances naturally deviate from expectations. The planning process itself, he argued, steeped commanders in the character and complexities of problems they might encounter, allowing them to adjust when the unexpected occurred.

Eisenhower expanded upon this principle with typical precision: when an unexpected crisis occurs, “the first thing you do is to take all the plans off the top shelf and discard them and begin again. But if you haven’t engaged in planning you can’t start to work, with any intelligence.” This distinction distinguishes strategic competence from simple improvisation. Trump’s government appears to have skipped the foundational planning phase entirely, leaving it unprepared to respond when Iran did not collapse as anticipated. Without that intellectual foundation, policymakers now confront decisions—whether to declare a pyrrhic victory or escalate—without the framework necessary for sound decision-making.

The Islamic Republic’s Key Strengths in Unconventional Warfare

Iran’s resilience in the wake of American and Israeli air strikes demonstrates strategic advantages that Washington seems to have underestimated. Unlike Venezuela, where a largely isolated regime collapsed when its leaders were removed, Iran maintains deep institutional frameworks, a sophisticated military apparatus, and decades of experience functioning under international sanctions and military strain. The Islamic Republic has developed a system of proxy militias throughout the Middle East, created redundant command structures, and developed irregular warfare capacities that do not rely on conventional military superiority. These elements have enabled the state to withstand the opening attacks and continue functioning, showing that decapitation strategies seldom work against states with institutionalised power structures and distributed power networks.

Moreover, Iran’s strategic location and geopolitical power grant it with leverage that Venezuela did not have. The country sits astride critical global trade corridors, exerts considerable sway over Iraq, Syria, and Lebanon through proxy forces, and operates cutting-edge cyber and drone capabilities. Trump’s assumption that Iran would surrender as swiftly as Maduro’s government reflects a serious miscalculation of the regional dynamics and the resilience of institutional states compared to individual-centred dictatorships. The Iranian regime, although certainly damaged by the assassination of Ayatollah Khamenei, has demonstrated organisational stability and the capacity to orchestrate actions within multiple theatres of conflict, suggesting that American planners fundamentally miscalculated both the objective and the expected consequences of their initial military action.

• Iran sustains armed militias across Iraq, Syria, Lebanon, and Yemen, complicating direct military response.
• Advanced air defence networks and decentralised command systems reduce success rates of air operations.
• Cybernetic assets and unmanned aerial systems offer unconventional tactical responses against American and Israeli targets.
• Command over critical shipping routes through Hormuz offers commercial pressure over international energy supplies.
• Institutionalised governance prevents state failure despite removal of supreme leader.

The Strait of Hormuz as a Deterrent

The Strait of Hormuz serves as perhaps Iran’s strongest strategic position in any protracted dispute with the United States and Israel. Through this narrow waterway, approximately one-third of global maritime oil trade passes annually, making it one of the world’s most critical chokepoints for global trade. Iran has repeatedly threatened to close or restrict passage through the strait if US military pressure increases, a threat that possesses real significance given the country’s military capabilities and geographical advantage. Obstruction of vessel passage through the strait would swiftly ripple through international energy sectors, sending energy costs substantially up and imposing economic costs on partner countries reliant on Middle Eastern petroleum supplies.

This economic constraint fundamentally constrains Trump’s choices for military action. Unlike Venezuela, where American intervention faced restricted international economic repercussions, military action against Iran could spark a global energy crisis that would damage the American economy and weaken bonds with European allies and additional trade partners. The prospect of strait closure thus serves as a strong deterrent against further American military action, providing Iran with a degree of strategic advantage that conventional military capabilities alone cannot deliver. This situation appears to have escaped the calculations of Trump’s war planners, who carried out air strikes without fully accounting for the economic consequences of Iranian response.

Netanyahu’s Clarity Against Trump’s Spontaneous Decision-Making

Whilst Trump appears to have stumbled into military confrontation with Iran through intuition and optimism, Israeli Prime Minister Benjamin Netanyahu has adopted a far more deliberate and systematic strategy. Netanyahu’s approach embodies decades of Israeli defence strategy emphasising sustained pressure, incremental escalation, and the maintenance of strategic ambiguity. Unlike Trump’s seeming conviction that a single decisive blow would crumble Iran’s regime—a misjudgement based on the Venezuela precedent—Netanyahu understands that Iran represents a fundamentally distinct opponent. Israel has invested years developing intelligence networks, establishing military capabilities, and building international coalitions specifically intended to limit Iranian regional power. This measured, long-term perspective stands in sharp contrast to Trump’s preference for sensational, attention-seeking military action that offers quick resolution.

The divergence between Netanyahu’s clear strategy and Trump’s ad hoc approach has created tensions within the armed conflict itself. Netanyahu’s administration appears committed to a long-term containment plan, equipped for years of low-intensity conflict and strategic contest with Iran. Trump, meanwhile, seems to expect rapid capitulation and has already begun searching for exit strategies that would allow him to claim success and move on to other concerns. This fundamental mismatch in strategic outlook undermines the cohesion of US-Israeli military cooperation. Netanyahu cannot risk adopt Trump’s approach towards early resolution, as taking this course would make Israel at risk from Iranian retaliation and regional competitors. The Prime Minister’s organisational experience and institutional recollection of regional disputes provide him advantages that Trump’s transactional, short-term thinking cannot equal.

The shortage of strategic coordination between Washington and Jerusalem produces precarious instability. Should Trump advance a negotiated settlement with Iran whilst Netanyahu stays focused on armed force, the alliance may splinter at a crucial juncture. Conversely, if Netanyahu’s drive for continued operations pulls Trump deeper into intensification of his instincts, the American president may find himself locked into a sustained military engagement that undermines his expressed preference for swift military victories. Neither scenario advances the strategic interests of either nation, yet both stay possible given the core strategic misalignment between Trump’s improvisational approach and Netanyahu’s organisational clarity.

The International Economic Stakes

The escalating conflict between the United States, Israel and Iran could undermine worldwide energy sector and disrupt tentative economic improvement across numerous areas. Oil prices have already begun to swing considerably as traders foresee likely disturbances to sea passages through the Strait of Hormuz, through which approximately one-fifth of the world’s petroleum passes daily. A sustained warfare could trigger an energy crisis similar to the 1970s, with cascading effects on price levels, exchange rates and investor sentiment. European allies, currently grappling with economic headwinds, face particular vulnerability to supply shocks and the risk of being drawn into a confrontation that threatens their strategic autonomy.

Beyond energy concerns, the conflict endangers global trading systems and fiscal stability. Iran’s possible retaliation could target commercial shipping, disrupt telecommunications infrastructure and prompt capital outflows from emerging markets as investors look for secure assets. The volatility of Trump’s strategic decisions exacerbates these threats, as markets work hard to factor in outcomes where American decisions could shift dramatically based on presidential whim rather than careful planning. Global companies conducting business in the region face escalating coverage expenses, logistics interruptions and regional risk markups that ultimately pass down to customers around the world through increased costs and diminished expansion.

• Oil price fluctuations jeopardises global inflation and monetary authority credibility in managing monetary policy successfully.
• Shipping and insurance costs escalate as ocean cargo insurers require higher fees for Gulf region activities and regional transit.
• Investment uncertainty prompts capital withdrawal from developing economies, worsening currency crises and government borrowing challenges.