Iran:  A Reality TV President Comes Face to Face … With Reality

At the time this was typed, the New York Times was reporting that there were “conflicting signals” as to the level of progress of negotiations between the Trump Administration and the Iranian Regime to resolve the current conflict.  When this is published, the two sides are again exchanging fire while still orchestrating negotiating sessions.  Who knows where they’ll be when you actually read this.

While any end to the current war will bring about the opening of the Strait of Hormuz on some basis, and thus, from a practical perspective, will over time alleviate the stress that the two sides’ actions have placed on the global economy, I don’t believe that the terms that they finally agree to will ultimately matter that much from a strategic geopolitical perspective. 

Over the last couple of months, I have written drafts of several posts about the Trump Administration’s assault on Iran never entered here (for which I am sure you are grateful 😉); each seemed to me to miss the essence of the encounter.  I would now offer this:  President Donald Trump took the strategic gamble that in attacking Iran, America was going to be able to remove the Iranian Regime.  Iranian Regime change was the key, the only key, to the mission.  The gamble failed.   

As all who care are aware, in the period immediately before America launched its military assault on Iran on February 28, Trump Envoys Steve Witkoff and Jared Kushner had been in negotiations with the Iranian regime about Iran’s stockpile of nuclear material (we’ll put aside the fact that the Trump Administration had already indicated that it had “obliterated” the material that it was still discussing with the Iranians), Iran’s development of a nuclear weapon, Iran’s sponsoring of proxies that spread terror and unsettled other governments within the Middle East and elsewhere, perhaps about Iranian’s ballistic missile capability, undoubtedly about what concessions Iran would have to make for America to provide economic relief for Iran – you know, all the normal stuff American administrations have been discussing with the Iranian regime, either covertly or overtly, for at least the last 25 years.  Mr. Trump ordered an attack on Iran not long after Messrs. Witkoff and Kushner returned to Washington and briefed him on the status of negotiations.

No matter what you think of the morality of Israel’s extended assault on Palestinians since Hamas’ attack on Israel in October 2023, recall that at the time when Messrs. Witkoff and Kushner briefed Mr. Trump, there was a general consensus among foreign policy experts that in the preceding two-plus years since the Hamas attack, Israel’s aggressive campaigns had weakened Iran by both striking at Iranian regime leadership and substantially degrading the capabilities of Iranian proxies such as Hamas and Hezbollah in Lebanon.

Recall that when Messrs. Witkoff and Kushner briefed Mr. Trump, most commentators were opining that Iran’s chief ally, Russia, given the Ukrainian quagmire into which it had blundered, needed assistance from its allies; Russia was seemingly not in much position to provide much assistance to the Iranian regime.

Recall that starting in late December, 2025, there had been mass rallies in Iran by citizens protesting the regime’s political repression and the country’s economic depression.  The protests were reported to be among the most, if not the most, widespread and vociferous faced by the Iranian regime in its decades in power.  Those protests had since been dispelled by the Regime’s massacre of thousands of protestors in the first two weeks of January, 2026.

Put aside whether Messrs. Witkoff and Kushner were the most appropriate of emissaries for these kinds of negotiations, and let’s play it straight here:  they probably told the President of the United States exactly what presidential advisors have been telling U.S. Presidents since 1979, probably what you, I, or any savvy American 14-year-old would have told Mr. Trump if we had been on the U.S. negotiating team:  No matter what they say, you can’t trust them.

It has been reported that at the same time as Messrs. Witkoff and Kushner were reporting back to Mr. Trump, Israeli Prime Minister Benjamin Netanyahu was telling the President that Israeli intelligence was indicating that the Iranian people would again rise up against the Iranian regime if America launched an assault.  Although its reputation for excellence was certainly tarnished by Hamas’ attack in October, 2023, Israeli intelligence has long been considered one of the best in the world, perhaps the best in the Middle East.

Finally, recall that on January 3, 2026, the American military had successfully snatched Venezuelan President Nicolás Maduro without losing a soldier, and the Trump Administration and replaced Sr. Maduro with a Venezuelan government leadership team amenable to American interests.  I don’t think it takes much to infer from the President’s own comments comparing Venezuela and Iran that his fascination with what seems to him to be American military omnipotence caused him to believe that when the Iranian Regime experienced the shock of America’s true military might, it would roll over as the Venezuelans had.

In a nutshell:  no matter what the Trump Administration says now, no matter the give-and-take, the back-and-forth, the moving goal posts, the details that the talking heads seeking to fill telecast and podcast minutes now dwell upon, I would repeat that the mission President Trump ordered had to have been really focused on only one objective:  effecting Iranian regime change.  Everything – all of America’s subsidiary objectives — fell into place if the Ayatollahs and the Iranian Revolutionary Guard were toppled, replaced by officials with sentiments similar to the other Gulf States.  Nothing sustainable was achieved if the Iranian Regime wasn’t toppled.  Recall that after the first assault assassinating the Ayatollah Ali Khamenei and the top echelon of the Iranian Regime, Mr. Trump kept talking about finding someone “to negotiate with.”  In those early days, he was anticipating an uprising by the Iranian people and looking for the emergence of the Iranian equivalent of Venezuela’s Delcy Rodriguez – somebody compliant. 

Despite my general sentiments about Mr. Trump, I would suggest that – except for his idiotic misconception that Iran was like Venezuela — the other factors he had in front of him made launching an attack on Iran an objectively closer call than it now appears.  Iran will indeed remain a destabilizing influence on the Middle East and the world as long as the current regime is in power.  Messrs. Witkoff and Kushner apparently understood that the day after the Iranians formally agreed not to build a nuclear bomb, they would find some desert cave and start building a nuclear bomb.  The Iranian regime and its proxies were in the weakest state they had been for decades.  Russia wasn’t in much position to assist Iran defend itself from any American attack, and China’s assistance would be muted at best.  The Iranian civilians had already shown their willingness to rise up, and Israeli intelligence is reported to have claimed that the Iranian citizenry would rise up again if inspired by an American assault.  (With the benefit of hindsight, it is also not unreasonable to surmise that both American and Israeli intelligence underestimated the extent and dispersion of Iran’s missile, drone, and like capability.)  When Mr. Trump was briefed, I wonder how much the potential ramifications on shipping through the Strait of Hormuz was even considered if the Trump Administration was confident that the Iranian regime would fall or capitulate when confronted by overwhelming American military prowess.

But … the regime hasn’t fallen or capitulated.  Now, no matter what “deal” the Trump and Iranian regimes ultimately cook up, this foray was a strategic American failure that will resonate for years, perhaps generations.  The Iranians have not only refused to be docile apprentices, refused to be fired; by choking the Strait of Hormuz they have spread molasses all over Mr. Trump’s gold-plated conference table.  Today, the Iranian regime is without doubt hardened and emboldened.  It will remain a destabilizing influence on the Middle East and the world.  It will take whatever finances it obtains as part of any settlement to strengthen its hold on power and refresh its proxies.  It (obviously) still can’t be trusted, and the American assault may only have increased the Iranian regime’s determination to build a nuclear bomb (I use the “may only” qualification because it was pretty darn determined before), and the day after it makes whatever nuclear representation it needs to make to get economic relief, it will find some desert cave and start to build a nuclear bomb.  Israel and the Gulf States are reportedly concerned – and if the reports are accurate, justifiably so – that Mr. Trump is willing to strike a deal that does not limit Iran’s ballistic missile and drone capabilities – the capabilities that present the most danger to them and their infrastructures today.  The Iranian regime can seemingly rest assured that if the civilian population was too cowed to rise up when the Americans attacked, they won’t be a challenge for a while.  Meanwhile, although it may be currently objectively militarily weakened by the American salvos, its global stature is enhanced simply by withstanding the American assault; the limits of American power and commitment have been demonstrated; Mr. Trump’s blowhard ambivalence has materially weakened America’s heretofore relationships with the Persian Gulf States; and even assuming that the agreement that the Iranian Regime ultimately works out with Mr. Trump provides for ships’ safe passage through the Strait of Hormuz with no “tolls,” its demonstrated capacity to strangle the Strait at will provides it significant implicit power it did not have before the assault.

It is clear that in this second term, Mr. Trump has primarily been engaged on a legacy-building spree from the East Wing ballroom to attempting to rewrite the reality of his 2020 election loss and the January 6th insurrection to the erection of the supposedly “Triumphal Arch” (which seemingly only lacks a McDonald’s at its top; no one does arches better than Mickey D’s 😉).  Had Mr. Trump’s assault on Iran successfully installed a replacement Iranian government whose disposition was aligned with other Gulf States – no more nuclear weapon threat, no more destabilization threat, perhaps providing greater freedoms to its citizens – even Trump naysayers such as myself would have recognized the Iranian foray as an historic legacy foreign policy achievement.  But … it didn’t work.  The President finds himself in a room with no exits. 

I recall from reading I did years ago (it might have been in David Halberstam’s The Best and the Brightest) an account of a senior military officer, lamenting after the Bay of Pigs invasion failed, that he should have made it clearer to President John Kennedy before the mission began that if Mr. Kennedy authorized the mission – which was supposed to be without American involvement — Mr. Kennedy could not allow it to fail – i.e., that if the American-sponsored Cuban insurgents weren’t successful in overcoming the Castro forces, and the Cuban populace didn’t rise up against the Castro Regime as American intelligence believed they would, Mr. Kennedy had to be ready to order a full-scale military invasion of Cuba to take out the Castro regime.  I recall other accounts of the Bay of Pigs incident suggesting that the generals around Mr. Kennedy assumed that if the insurgents didn’t succeed, the President would feel unbearable pressure to commit American forces.  Obviously, despite the complete collapse of the covert invasion, Mr. Kennedy elected not to commit American troops to sustain it.  Some historians maintain that what then appeared to be Mr. Kennedy’s lack of resolve was what tempted Soviet Leader Premier Nikita Khrushchev to subsequently attempt to place nuclear weapons in Cuba.  (I understand that most historians now believe that Mr. Kennedy was right to hold back in 1961, although such was not nearly so clear at the time.  Even without the benefit of the hindsight of the favorable outcome of the 1962 Cuban Missile Crisis, perhaps the wisdom shown by the President’s restraint arose from his experience in the World War II Pacific island-to-island theater; perhaps he understood that Cuba was bigger, with more difficult terrain, than some supposed, and that unseating the Castro regime would be more difficult than many imagined.  Factors that the Trump Administration might be well to consider.  The Castros haven’t stayed in power for over 65 years by being stupid, and have been waiting for an American invasion even longer than the Iranians had.  But that’s a different blog.)

Maybe we’ll know from some future account – although we’ll have no reason to place any greater faith in the veracity of any member of the Trump Regime than we do in the Iranians – whether the Trump team was so sure that the Iranian regime would fall if Mr. Trump ordered the attack that none of the President’s advisors placed directly in front of him – really made him consider — whether he was willing to deploy ground troops, and incur American deaths, to “finish the job” if the regime didn’t fall.  Given Mr. Netanyahu’s demonstrated tendencies, it’s not difficult to suppose that he assumed, like the generals around Mr. Kennedy may have in 1961, that Mr. Trump would commit American forces rather than suffer what will would look like a humiliating setback.  It certainly now appears the Mr. Trump is unwilling to do so.  I’m not going to question which is the right course; while there are strong objective arguments on both sides, given Americans’ manifest lack of support for the war, there really is only one side.  The President clearly has greater fear of the political backlash that would accompany any American casualties and continuing disruption of the global economic system from what would be an extremely domestically unpopular ground war than he does of the continuing threat that the Iranian regime creates for geopolitical stability and America’s Middle East allies. 

The Reality TV President is looking for a commercial break.  There isn’t one.  He has come face to face with … Reality. 

There is one silver lining to what now appears to be an impending American humbling – and I consider it to be a lining wide, bright and shiny for those currently deeply concerned about the threat that Mr. Trump and his cohort present to true American democracy.  Had Mr. Trump’s Iranian venture been successful, I would expect that his popularity would have risen substantially despite the economic distress currently suffered by a significant majority of our citizens.  The President and his MAGA acolytes, rather than the Iranian regime, would have been both hardened and emboldened.  It is not difficult to suppose that he and they would have ratcheted up their frankly fascist repressive domestic measures – through criminal prosecutions, election interference, National Guard deployments, ICE’s Sturmabteilung activities, protester surveillance, a declaration of Martial Law allegedly necessary due to Iranian terrorist reprisals, and the like — against those whom they consider their political enemies.  As the Iranian negotiations now seem likely to conclude indecisively, it is hard not to believe that Mr. Trump — after having spent billions of taxpayer dollars on an ill-fated effort half a world away that increased Americans’ cost of living and diverted the Trump Administration’s attention from other issues most Americans care about much more than Iran — is going to look like a loser to all American citizens but his hardest-core, most brainwashed MAGA base.  (That “Triumphal Arch” could quickly become a mocking symbol of an American embarrassment.)  I am more than happy to suffer a temporary reduction in American global prestige – which, as Mr. Kennedy proved during the Cuban Missile Crisis, can be retrieved in the future by a future courageous and skillful American president — if such enhances our ability to preserve American democracy today.

We’ll see what happens.

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