I Wargamed Iran for Obama. This Is the Worst-Case Scenario
As a former US official, Ilan Goldenberg spent years gaming a conflict with Iran. Here are 5 lessons he learned that Trump hasn't.
Earlier this week, Donald Trump was asked whether he was surprised that no one briefed him in advance that Iran might respond to an American attack by targeting Gulf countries. His response? “Nobody. Nobody. No no no.”
That is evidence that either Trump is lying or his administration has so cut itself off from experts that no one briefed him on what was essentially common wisdom amongst US experts – that major strikes on Iran could prompt Tehran to respond by targeting oil infrastructure and US bases across the Middle East and closing the Strait of Hormuz.
For the past 15 years, I’ve participated in and helped run scenario exercises and war games on Iran both at the Pentagon and then outside of government. These exercises are not about predicting the future with certainty. They are about understanding the possible consequences of choices.
And on Iran, the lessons from these exercises were remarkably consistent and quite similar to what we’ve seen play out over the past two weeks. Here are five things Trump should have known and would have known if his administration had listened to experts:
1. When the regime feels existentially threatened, Iran will escalate
In most war games, conflicts began at a lower level: an Israeli strike, a proxy attack, a miscalculation. At that stage, Iran usually calibrated its response. It retaliated, but tried to avoid drawing the United States fully into the conflict because it knew that a full-on war with the US represented a massive threat. That pattern held in real life during the Israel-Iran exchanges of 2024 and 2025.
But once the United States entered directly, and once the regime believed its survival was at stake, those restraints would disappear.
At that point, Iran’s playbook was well understood: strike US bases, harass shipping in the Gulf, activate proxy forces across the region, and target oil infrastructure and civilian assets. The goal was to impose costs, spike oil prices, and create international pressure on Washington to stop.
This was not hard to foresee. It was one of the most consistent conclusions in the exercises I saw. What we are watching now was entirely predictable.