Anatomy of a Gamble

The Memorandum of Understanding signed by US and Iranian representatives in Switzerland on Friday almost certainly brings to an end the Middle East war that commenced with the Hamas attacks on Israeli communities of October 7, 2023. The trajectory of the war may already be traced. Its longest phase, from October 2023 to October 2025, follows an easily understandable pattern in which an initial act of aggression by one component of a regional alliance, Hamas, was then followed by the piecemeal mobilization of the various elements of the (Iran led) alliance of which it is a part. Lebanese Hezballah entered the fray first, on October 8, then the Yemeni Houthis in November of that year, and then Iran itself in April of 2024. The subsequent process, from mid 2024 until late 2025, was one in which Israel, accompanied in part by the United States, systematically degraded the capacities of Iran and its various clients and proxies across the region, leaving them bruised and bloodied by the years’ end.

The last phase of the war, now concluded, ran from February 2026 until June 2026 and has followed a rather different path. It was initiated by Israel and the United States with the clear intention of finishing the job, and leaving the Iranian regime either destroyed or severely strategically weakened. These aims have not been achieved. Rather, Tehran has emerged from this last chapter strengthened on the strategic level. This final phase of the war was a strange affair, based on a series of Israeli and American misjudgements, which together have combined to produce a damaging and negative conclusion. Taken together, these amount to a significant mis-step, which has allowed a powerful anti-western regional bloc based on a shared commitment to political Islam to demonstrate its own strengths and turn these into achievement. Let’s take a look at this series of misjudgements and how they were able to produce this outcome.

Why was the war re-launched on February 28^th? There was no clear and immediate danger. To be sure, Iran retained possession of 440 kg of heavily enriched uranium, and a much larger amount of uranium enriched to lower levels. But Tehran’s nuclear facilities had suffered massive damage in the US’s Operation Midnight Hammer and Israel’s Operation Rising Lion in June, 2025. The key installations at Isfahan, Fordow and Natanz were all targeted and all suffered severe structural blows. Iranian efforts at excavation and construction of new facilities were under way. But there is no evidence that these had reached a critical point making renewed intervention urgent. Certainly, no proof has been offered to indicate that an Iranian decision to attempt an immediate breakout to nuclear weapons capacity had been made.

With regard to Iran’s missile array, similarly, while Tehran was attempting to accelerate its repair of missile facilities from the massive damage suffered in mid-2025 (60% of ballistic missile launchers destroyed at that time, according to one estimate), it had not yet come close to return to the capacities possessed on the eve of that war. In April and October of 2024, Israel and its allies proved that in the field of air defense, they were able to successfully divert the best efforts of Tehran’s missile and drones to strike at Israeli civilian and military targets. The degraded capabilities of early 2026 presented no clear and imminent threat.

Rather, it’s clear that Israel’s leadership surveyed their considerable military achievements, observed the massive Iranian popular demonstrations against the regime in December, 2025 and January, 2026, and considered that the regime was ripe for the coup de grace.
This appears to be the case that Prime Minister Benjamin Netanyahu presented to President Donald Trump on February 12 at the White House. According to reporting in the New York Times and the Jerusalem Post, an argument was made by videolink at that meeting by Mossad espionage agency head David Barnea for the possibility of regime change, utilising a combination of aerial bombing and covert action on the ground.

Details of the Israeli plan have since become publicly available. The American scepticism appears well founded. The plan seems to have been wildly ambitious. An example: in its initial stages, it was meant to involve the entry of Iranian Kurdish militias from Iraqi Kurdistan across the border into the Iranian province of Kordestan. The militias in question (the PDKI, Komala, PAK, Khabat and PJAK) are small political military groups, with a combined strength of about 8000 fighters. I have visited the bases of three of these groups and interviewed the leaderships of four of them, over the years. The most formidable of them is PJAK, which is the Iranian Kurdish franchise of the PKK organization. PJAK, however, declined to participate in the operation.

So the plan included provision for a tiny and lightly armed force of probably not more than 5000 fighters to launch an armed incursion into a province characterized by a very heavy presence of the Islamic Revolutionary Guards Corps (IRGC). Success would have been predicated on Israeli air support but more crucially on the very rapid rallying of tens of thousands of young Iranian Kurds around the banner of revolt. This has the manner of a wild gamble assuming the extreme fragility of the regime, which as it turned out was an illusion. The Israeli alliance with the Iranian Kurds was rapidly cobbled together in the months preceding the renewal of hostilities. It is almost certainly to the benefit of the Iranian Kurds that the incursion did not take place.

Why did Israel misjudge the vulnerability of the Iranian regime? In the same way that Iran overestimated its conventional capacities in 2024, and foolishly chose to take on Israel in that arena, so Israel in 2026 failed to factor in the Tehran regime’s own areas of strength – namely its capacity for internal repression, but also the durability and strength of its core nucleus of support in Iran, and of its proxy militias in the Arab world.

Israel may have made an over optimistic presentation of the situation to the US. But the administration did not concur with the Israeli estimate or plan in its entirety. The Mossad’s presentation received mixed reviews from the US listeners present. Trump chose to go with the more limited option suggested by Secretary of State Marco Rubio: a massive bombing campaign that would inflict huge damage but avoid committing the U.S. to a prolonged effort to reshape Iran’s internal governance. Interestingly, however, once the air campaign began on February 28^th, the administration’s public messaging seemed to adopt the maximum goal anyway.

“The hour of your freedom is at hand,” the US president signalled to the Iranian people as the bombing started. “"There will be no deal with Iran except UNCONDITIONAL SURRENDER!” he declared on March 6.

Once the regime didn’t fall, it appears that there was no Plan B. Worse, the Administration doesn’t seem to have reckoned with the possibility that the Iranian regime might seize the Strait of Hormuz. Once that seizure took place, and the US determined that the cost in blood and treasure of reopening Hormuz by force wasn’t worth paying, it was only a matter of time before something resembling the current MOU was bound to arrive.

It is difficult from all this not to draw the conclusion that the US Administration entered the war on February 28 without a proper analysis of what the Iranian regime was, and of its strengths and weaknesses. The president was correct, as he often noted, that Iran has little left by way of a navy. “Their navy is totally gone - 100 per cent” he told Fox News recently. “The air force is totally gone - 100 per cent.”

The problem with this is that the particular strengths possessed by the Iranian regime are not located in the field of conventional air or sea power. The regime in Tehran is an Islamist, ideological gathering, engaged in a ‘forever war’ of its own, of society against society, rather than army against army. Its practical successes both in retaining power in Iran and in building influence and strength from the Gulf of Aden to the Mediterranean derive from its ability to mobilise (mainly but not only) Shia Muslim loyalties and commitments, and to use these as the engine for political and paramilitary mobilization.

It is likely that nothing like this really exists in Trump’s world. One imagines him and those around him dismissing such issues as unreal or unimportant, assuming that in the end, everyone’s motives are similar, everything is for sale and a deal can always be reached. His remarks this week following exchanges of fire between Israel and Iran that “each of them had their fun” but that now it was time to “get back to the table and make a deal” appear redolent of such a view.

Trump, caricatured before his presidency as a warmonger, is nothing of the kind. The place, very clearly, where he feels comfortable is where deals are made. And in particular, where deals reflecting the greater physical strength of his side are concluded, with the other side coming to understand the benefits of accepting the power differential and understanding how it can gain from it.

The problem is that the Islamic Republic of Iran is not an entity interested in playing this role. The US could have forced it back. But the political support for the inevitably costly means required to do this wasn’t there. The US urgently needed Gulf oil to start flowing again to international markets. Hence the current MOU, granting Iran an effective restoration of the status quo antebellum, with some added benefits.

The government of Israel appears to have believed that the US administration adhered to a similar analysis of the Middle East to its own. The present administration’s participation in the war alongside Israel in June, 2025, and its many previous actions in support of the Israeli position may understandably have inclined Jerusalem towards this conclusion. Trump’s moving the embassy to Jerusalem in his first term, his killing of IRGC Qods Force leader Qassem Soleimani in January 2020, his recognition of Israel’s ownership of the Golan Heights and his brokering of the historic Abraham Accords further reinforced this impression. But this sense failed to take into account a number of countervailing elements. These include: the president and his supporters’ determination not to be drawn into new major commitments in the Middle East, a region which they consider to be of secondary importance to the American strategic interest. This wouldn’t have mattered if victory had been swift, of course. The Israeli underestimation of Iran mentioned earlier seems to have inclined Netanyahu to think it would be so. It wasn’t.

Jerusalem also underestimated Trump’s capriciousness and short attention span, and his capacity for abruptly and rapidly reversing his position. Israel also failed to take into account the growing importance of Turkish and Qatari perspectives and messaging at the top levels of the administration, via the influential positions of Middle East Envoy Ambassador Tom Barrack, and Special Envoy Steve Witkoff. Both Ankara and Doha hold to a cardinally different analysis of the Middle East which is in most ways antithetical to the Israeli interest. The growing influence of this rival analysis was evidently not accounted for.

Lastly, Israel may have underestimated the genuinely deleterious effects on the US and on the administration’s standing of surging gasoline prices and inflation as a result of the continued blockading of the Strait of Hormuz.

All this has produced a conclusion very far from what Jerusalem or Washington may have hoped for. The Iranian regime is damaged but intact, now under the control of a new, militant and ideological leadership centered on figures coming from the upper reaches of the IRGC.

Clause 1 of the MOU includes a call for ‘an immediate and permanent end to the war on all fronts, including Lebanon,’ linking Israel’s actions against Hezballah in that country with the broader settlement with Iran. Israel had striven to keep the two arenas separated so as to preserve its freedom of action in defense of its northern border communities. Trump’s latest statements suggesting that Syria should engage against Hezballah in Lebanon in place of Israel once more confirm the influence of the Turkish and Qatari perspectives on this White House, via Ambassador Barrack.

The MOU also agrees to the ‘ending, on a schedule to be agreed upon as part of the final agreement, all types of sanctions currently facing the Islamic Republic of Iran, including resolutions of the United Nations Security Council and the Board of Governors of the International Atomic Energy Agency (IAEA), and all unilateral U.S. sanctions, both primary and secondary.’

So the gamble didn’t pay off, predicated as it turns out to have been on a series of misreadings, on the part of both Israel and the US administration. The final question is why – that is, why did Netanyahu, not usually a politician known for recklessness, choose to bet on what ought to have looked at best like an uncertain outcome. Here one enters the realm of intangibles, of course, and one can only speculate. My own view, for what it’s worth, is as follows:

The Israeli Prime Minister wanted to present the people of Israel and the world with the Iranian regime’s head on a plate. I think he wanted to do that because 1. he thinks Iran is the chief danger to Israel’s security and 2. because he understood that unless he could conclude the two years of war with the destruction of the Iranian regime or something on that level of magnitude, he would be remembered, despite subsequent achievements, as the prime minister of October 7. that is, only a victory on that level of magnitude would change that historical perception, in the same way that no-one remembers FDR as the president of Pearl Harbor, because of the subsequent total defeat of the enemy who carried that out. This is only my idle thought, not based on sourcing. In any case, whatever the motivation behind the gamble, it hasn’t worked. The result is that Israel is now set to face the continued onslaught of the Iran led regional axis, which remains committed to its destruction. It is set to do so, for the next period, without the clear backing of its superpower ally.

Published originally under the title “Failure of Judgment: How U.S., Israel Overplayed Hand on Iran.”