It may never be known whether Trump assumed that conventional bombing of Iran would produce a Venezuela-like outcome, with the regime collapsing and agreeing to do Trump’s bidding, or not. But what has become overwhelmingly clear, long before Trump’s surrender to Iran, was that there was no consideration of what Iran would do with the Strait of Hormuz or Plan B strategy if the regime survived.

Perhaps it would have gone smoother had Trump focused on a goal in advance of an unlawful war rather than throw things against the wall and see what would stick, thereby being able to sell the war to Americans as worth the cost, in terms of lives and money. It surely would have gone better had Trump not blathered about how we won, we decimated Iran (as opposed to obliterated their nuclear program a few months earlier), how Iran was nice to him and agreed to everything he wanted. And oh yeah, how he was in control of the Strait of Hormuz, a critical international waterway that was open to all before he started the war and was now closed, whether by Iran, the United States or both.

Then came the surrender, the Memorandum of Understanding crafted by the brilliant international diplomat, Steve Witcoff, Jared Kushner, the president’s son-in-law who has no official role in government but is busy soliciting money for his hedge fund, and the Vice President, J.D. Vance, who did everything in his power to dissociate himself from responsibility because “I don’t know nothin’ about birthin’ no babies.” It was doomed, lasting for a few hours before the bombs began and the ships stopped. No one expected otherwise.

When confronted with this scenario, there are a few options on the table.

1. Do nothing.
2. Make it better.
3. Make it worse.

Trump declared the ceasefire is over and recommenced bombing, lack of congressional approval notwithstanding, stockpiles of armaments heading toward depletion and costs mounting. And Trump, being Trump, kept digging. After calling the Iranians “scum” and “sick,” something that always helps when seeking a diplomatic way out of a debacle, Trump dug even further.

How this will be explained in light of Little Marco Rubio’s earlier, and correct, statement that it is contrary to international law to charge tolls remains something of a mystery.

Secretary of State Marco Rubio on the Strait of Hormuz: “No country is allowed to charge tolls or fees on an international waterway.” pic.twitter.com/BOBBfiDN43

— CBS News (@CBSNews) June 23, 2026

Will Trump re-evaluate his impetuous claim to 20% of the value of good traveling through the Strait of Hormuz after being informed that it’s neither lawful nor something he has the authority to do? Has he ever admitted error before? Sure, he’s smarter than all the generals, not to mention everyone else, if he does say so himself, but even a stable genius can make a mistake. But it takes a bigger person than Trump to admit it.

Now that he’s made this wild if unlawful and ultra vires claim, atop his many other adventures in warfighting, has he dug himself into a hole too deep to get out? Is there any strategy that will enable the United States to end this war? Will more bombing produce a different result than bombing did before? Can the Strait of Hormuz ever return to its former status as a free and open international waterway now that Iran knows it can close it at will, and force the world to either fight it or drop to its knees?

Has Trump foreclosed any possibility of a diplomatic end, whether surrender with or without honor, because of his mercurial moods and unrestrained impulse to play the tough guy? How does this disastrous war end? How does Trump back down from his wild if ridiculous claims of victory and mastery, having left himself no room to pretend he has not lost his war of choice? Or will he just pretend that none of this ever happened, confident that the MAGA faithful will shut their eyes very tightly and believe him despite every fact to the contrary?

Where do we go from here?

*Tuesday Talk rules apply.