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The Heroes' Path Brief: Iran Update #4

March 27, 2026

Four Weeks In. Nobody Planned for This.

Day 28 of the war with Iran.

That number matters, because the people who planned this thing expected to be done by now. Three weeks, four at the outside. Shock and awe, a weakened Revolutionary Guard, and then jubilant Iranians pouring into the streets to finish the job. That was the picture in Washington and Tel Aviv when this started.

It didn’t go that way.

The Strait of Hormuz is now a toll road: $2 million per transit, collected by the Iranians, for ships they’re gracious enough to let pass. Patriot missiles are running low. The IDF Chief of Staff told his own cabinet this week that his force is on the road to collapse if they don’t get 15,000 more troops. The diplomatic channel that opened this week looks, depending on who you ask, either like the beginning of a deal or the cover story for a surprise ground assault. Russia trained Iranian forces before the shooting started. Three thousand people are dead and that number goes up every day.

Jeff Steinberg has been on the Heroes’ Path podcast three Fridays running. He comes prepared. He’s been right throughout. Tonight, we sat down with him again to ask the questions that don’t have clean answers yet: who actually wants this war to end, and what does ending it even look like now that the early assumptions are gone.

Twenty-five minutes. No spin. Worth your time.

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