Trump is setting himself up to fail in Iran for the same reason he won in Venezuela

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Three recent major geopolitical confrontations teach a consistent lesson: overwhelming military power alone cannot produce the desired political outcome. Ukraine, Venezuela, and Iran differ vastly in culture, geography, and strategy, but together they illustrate an enduring rule of statecraft: If you intend to force fundamental change on an adversary, you must know how to engage it from both without and within.

Russian President Vladimir Putin learned the first half of this lesson the hard way. When Russia launched its full-scale invasion of Ukraine, Moscow anticipated a swift collapse, but that didn’t happen. Instead, Putin badly miscalculated on two fronts:

First, the Ukrainian military was no longer the fractured force Russia encountered in 2014. By seizing Crimea and backing separatists in the Donbas, Russia unintentionally handed Ukraine eight years to reform, train, and build hard-won combat experience. 

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Second, and more critically, Ukraine’s internal political order held fast. President Volodymyr Zelensky stayed in Kyiv, state institutions remained operational, society mobilized, and Western support poured in. Russia struck hard from the outside, but it failed entirely to break Ukraine from within.

The Trump administration’s operation against dictator Nicolas Maduro’s regime in Venezuela presents a striking contrast. Unmatched American military force and intelligence capabilities proved decisive. Yet force alone does not explain why Maduro’s capture avoided leaving a chaotic power vacuum behind. Long before troops arrived, Washington was already cultivating key figures inside the Venezuelan political architecture.

Subsequent reporting confirmed that high-level regime figures — including then-Vice President Delcy Rodriguez and National Assembly President Jorge Rodriguez — had maintained discreet backchannels with U.S. and regional intermediaries, signaling a readiness to cooperate once Maduro was removed.

Real changes come from the inside out

That preparation mattered enormously. Washington did not simply decapitate a government and ask, “What happens tomorrow?” It leveraged existing lines of communication into the surviving power structure. Rodriguez assumed office as acting president, institutions remained functional, and the government swiftly moved toward pragmatic engagement with Washington.

The post-Maduro Venezuela government has even initiated the phased release of political prisoners. While critics argue the U.S. interest remains driven largely by access to Venezuela’s energy reserves, the early results suggest something broader: the groundwork for gradual structural reform and a path toward political and economic normalization.

Iran, however, represents a far more dangerous dilemma. Recent joint U.S.-Israeli strikes demonstrated extraordinary kinetic reach, proving that even Tehran’s senior leadership can be penetrated and targeted. But eliminating top officials is fundamentally different from transforming the underlying political system.

Prior intelligence assessments explicitly warned that targeted assassinations could produce the exact opposite of the desired result, potentially driving power straight into the hands of harder-line factions within the Islamic Revolutionary Guard Corps. The rapid rise of Ayatollah Ali Khamenei’s son, Mojtaba Khamenei, as his successor only reinforces this point — signaling little pragmatism or willingness to diverge from his father’s hard-line course.

Military force is an extension of political strategy, not vice versa

This reality exposes a glaring strategic gap: Who holds the legitimacy, organization, and authority to succeed the old guard? Which factions — clerical, military, or economic — might accept a restructured relationship with the West or anchor a transition? Were any internal channels cultivated before the ordnance was dropped?

Military firepower can obliterate command posts, nuclear facilities, and key leaders. It cannot manufacture a functional political order from the rubble. Furthermore, unlike Venezuela, Iran retains vast capacity to inflict asymmetrical costs on the international community. Leveraging its strategic position along the Strait of Hormuz, along with a formidable regional arsenal of ballistic missiles and proxies, Tehran can absorb external pressure and retaliate aggressively rather than capitulate.

None of this suggests that Washington and its allies should avoid confronting adversary regimes; Iran’s regional hostility and nuclear ambitions demand a firm response. But coercive statecraft requires political preparation equal to military execution — not just target lists.

The broader lesson from Ukraine, Venezuela, and Iran is not that force is obsolete — it remains an indispensable instrument. Rather, force achieves lasting success only when tied to an internal political lever within the adversary’s system. Pressure from without creates the structural shock; engagement from within converts that momentum into stable, strategic change.

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If President Donald Trump’s ultimate goal is to force a genuine transformation or bring a rival — Iran, for example — to the bargaining table, it must ask the crucial question: is there a viable “within” strategy ready to deploy? Without internal channels, popular momentum, or a clear architecture for succession, tactical success will consistently fail to yield strategic victory.

Destroying the old order is always the easier task. Knowing what replaces it is what separates a dramatic military campaign from a successful strategy and enduring victory.

David W. Wang (@DavidWWang203) is a senior international business executive, geopolitical affairs consultant, analyst, and writer based in the Washington, D.C., metro area.

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