A high school friend I’ve known for close to 60 years asked me that yesterday just after President Trump unilaterally announced a new “deal” to end the war. Trying to avoid his question, I told him that I had no way of knowing because I gave up my security clearance some years ago and I have no privileged access to people who are making the decisions now. He said that for our conversation purposes my best guess would suffice.
The short answer is yes, I suspect the Iran War will drag on for some time. My best guess is that we are looking at two possible scenarios:
President Trump continues to decide each evening what new ploy we will try the next day, (1)
The Trump Administration belatedly decides on a war strategy and sticks to it with a modicum of discipline.
The first scenario cedes the strategic initiative to the brutal new Iranian regime. The history of the 1979-80 Iran Hostage Crisis suggests that this will lead to the current war dragging on until 20 January 2029, when America inaugurates a new President.
In the second scenario, America takes back the strategic initiative and creates a reasonable possibility that in a messy 12 months or so we can get back to the status quo ante - meaning the free flow of maritime traffic through the Strait of Hormuz but continued uncertainty regarding an Iranian nuclear weapons program.
Negotiating with The New Iranian Regime?
On and off for the last few months, America has been trying to negotiate with the new regime in Teheran. This new regime is run by the Sepah, Persian for the “Corps.” In English we more formally call it the Islamic Revolutionary Guard Corps or IRGC.
Any Iranian can tell you that there are no moderates in the Sepah. They may pretend to negotiate but what they want is revenge, including revenge for President Trump’s 2026 assassination of their Grand Ayatollah Ali Khamenei and revenge for President Trump’s 2020 assassination of their hero General Qasem Soleimani.
The Sepah will never agree to anything proposed by Trump’s America. For them, this is a fight to the finish and they think they are winning. Negotiating with them is worse than a waste of time, it allows them to make President Trump look as foolish as President Carter did back in 1979-80.
Having Started this War, What Do We Do Now?
To limit damage to our vital national interests, America needs to take back the strategic initiative and keep it. The most promising way of doing this would probably be strict enforcement of the US naval blockade of Iranian shipping. Imposing the naval blockade on 13 April was an improvisation but it was a smart one. Hats off to whomever recognized that time was on our side. In May, the President was rightfully confident that America could bear moderate economic pain much longer than Iran could bear severe economic pain.
But as his 80th birthday approached on 14 June, the President seemed to panic. He agreed to a vague Memorandum of Understanding with the brutal Iranian regime, walked away from the blockade which was working, and got less than President Obama got in 2015 on the nuclear front. This was an unforced error.
President Trump is who he is. But if he is at all concerned with his historical legacy, he needs to (a) find a new Secretary of Defense in whom he has confidence and (b) give that Secretary some rein to coherently execute an Iran War strategy that better serves American vital national interests. Pete Hegseth is clearly not up to that challenge. Maybe John Ratcliff is.
For more, please check out my website above.
(1) For more detail see What Just Happened in Iran - Bruce Held, A Spy’s Guide to America’s Future, 19 June 2026
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