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Now Trump, and the Iranians, find themselves in a familiar predicament. The latter are once again facing American military attacks across their territory, underlining their inability to defend their territorial sovereignty. With the reimposed blockade, their oil revenue – a lifeline for the Iranian regime – is again cut off.
Meanwhile, Trump is again facing a choice between escalation, which comes with domestic economic and political costs, and settling for some kind of resolution that leaves a hostile Iranian regime in power.
"We're back to where we were initially, where the question was: who's got more patience?" said Elliot Abrams, senior fellow for Middle Eastern studies at the Council on Foreign Relations. "The Iranians, who will not be able to export oil, or the US and other countries that use Persian gulf oil?"
After months of concern that the Iran war was triggering a new round of popularity-crushing inflation, Trump received some good news on Tuesday that consumer prices were dropping.
A resumption of full hostilities, or even an escalation in the conflict, would inevitably push oil prices back toward previous highs, endangering that positive trend and again putting Republicans in a tenuous position heading into November's midterm congressional elections.
On Monday, after Trump's Truth Social post, the price of a barrel of oil jumped nearly 10% - the biggest one-day increase in six years.
The first time around, Trump's blockade helped pressure the Iranians to the negotiating table and set the table for the memorandum of understanding and a framework for a more lasting peace.
Now, according to Kelanid, the president's leverage over Iran may be diminished.
"He has already tried the things he can easily do, can credibly do," she said. "He can attack military targets, regime targets. He's done that before, and it didn't cause Iran to surrender."
The latest target Trump has suggested is Pickaxe Mountain, a heavily fortified nuclear research site south of Tehran. But there is conflicting evidence of the value of the site – or of whether US airstrikes can cause significant damage to the tunnels which are deep beneath granite rock.
If Trump's latest moves do ultimately end with yet another ceasefire and face-to-face talks, the underlying, difficult-to-reconcile disagreements – over Hormuz, over the disposition of Iran's nuclear programme, over Iran's influence in the Middle East - remain.
"I think there's room for negotiation here over a Strait of Hormuz deal," said Abrams. "But not a return to the MOU."
With the war approaching its fifth month, Trump again on Monday noted that other American conflicts – including the Vietnam War – stretched on for years.
That particular quagmire, however, hobbled and ultimately ended the presidency of Lyndon Baines Johnson and damaged US global standing for at least a decade. That is a fate Trump is certainly hoping to avoid.
His supporters also are weary to repeat the kind of Middle East "forever wars" that Trump condemned in previous presidential campaigns.
But with the memorandum of understanding in tatters, the ceasefire ended and the prospect of further conflict looming, the end of the Iran War appears no closer to a resolution than it was in the weeks after it began.
