Opinion

Iran is gambling that Trump will cave. It hasn’t gone well for them so far

Decades of half-measures have failed and the regime survives on time, ambiguity and Western hesitation

By Erfan Fard Fox News

Published May 20, 2026 5:00am EDT

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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 Donald Trump 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 Islamic Republic of Iran 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 1979’s revolt, when a profound failure of judgment in Washington reshaped the Middle East. The removal of the late Shah, Mohammad Reza Pahlavi — America’s 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.

FROM HOSTAGE CRISIS TO ASSASSINATION PLOTS: IRAN’S NEAR HALF-CENTURY WAR ON AMERICANS

An Iranian flag is placed amid rubble and debris next to a destroyed residential building near Ferdowsi Square in Tehran on March 3, 2026. (ATTA KENARE / AFP via Getty Images)

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 Iraq 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 broke the pattern. He did not reinterpret the system; he confronted it. In doing so, he changed the balance of........

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