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Reading: Iran is gambling that Trump will cave. It hasnt gone well for them so far
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Iran is gambling that Trump will cave. It hasnt gone well for them so far

Last updated: May 20, 2026 1:55 pm
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Iran is gambling that Trump will cave. It hasnt gone well for them so far
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As reports emerge of a possible new phase of confrontation between the United States and the Islamic Republic, one reality is becoming increasingly clear: the ruling system in Tehran still does not fully believe President is prepared to go beyond pressure and fundamentally alter the balance of power.

History does not remember those who merely manage crises. It remembers those who confront — and dismantle — the ideologies that produce them. The 20th century proved this decisively: Nazism, fascism and communism once appeared immovable, yet each ultimately collapsed under sustained and determined pressure.

The belongs in that same category. It is not a state that evolves toward moderation. It is an ideological system that sustains itself through repression, deception and expansion.

The roots of this challenge trace back to 1979s revolt, when a profound failure of judgment in Washington reshaped the . The removal of the late Shah, Mohammad Reza Pahlavi — Americas most reliable regional ally during the Cold War — created a vacuum that was filled not by democratic forces, but by a radical clerical mafia whose nature was neither fully understood nor seriously examined. Critical warnings were dismissed. The ideological foundations of Khomeinism were underestimated. Even its core texts were never meaningfully studied by those responsible for shaping policy.

What followed was not transition, but collapse — chaos hardening into theocratic power, and a system built on absolutism, coercion, violence and perpetual ideological expansion.

For decades, successive U.S. administrations attempted to manage this reality — through engagement, negotiation or strategic patience. The outcome was consistent: the steady expansion of a destabilizing force across the region. From to Lebanon, from Syria to Yemen, the Islamic Republic constructed a transnational terrorist network of militias and proxies, forming what is now widely recognized as the “Shia Crescent.” The war on terror, launched in 2001 at immense cost, failed to confront its central engine of instability.

Then came Donald Trump — and . He did not reinterpret the system; he confronted it. In doing so, he changed the balance of power.

Unlike his predecessors, he refused to treat the Islamic Republic as a state actor capable of reform through diplomacy. He recognized it for what it is: the epicenter of a transnational ideological project rooted in coercion, expansion, and permanent conflict. And he acted accordingly.  

The elimination of Iranian Maj. Gen. Qasem Soleimani was not simply a tactical strike. It was a strategic rupture in the modern Middle East. Soleimani was the architect of Irans regional Islamic terrorist network — the connective force linking proxy structures from Baghdad to Beirut. Removing him disrupted not only operations, but the regimes sense of reach and impunity.

For the first time in years, the system — effectively a Shia Islamic caliphate centered in Tehran — was .

Trump followed this with another unprecedented decision: terrorist organization. It exposed the regimes core institution as what it has long been in practice — a transnational instrument of ideological warfare, not a conventional military force.

Clarity puts pressure on your adversary. Ambiguity lets it breathe. The impact was felt far beyond Washington.

For millions of Iranians — nearly 90 million people living under repression — this was not abstract policy. It was one of the rare moments when reality. For many, Trump came to represent the possibility of breaking the grip of a regime that has held the country hostage for decades.

That distinction is not semantic. It is strategic. Yet the story remains unfinished. But pressure is not resolution. At critical moments, escalation and incomplete follow-through introduced ambiguity into an otherwise clear framework. Time was given back to a system that survives on time.

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