In the two months since U.S. President Donald Trump agreed to a ceasefire with Iran after initiating a joint offensive against the Islamist regime on Feb. 28, the whole world has been wondering what he is going to do next.
He’s faced with a difficult choice. The president is under enormous pressure to end the war and lower gas prices—primarily because of the damage it’s doing to the Republican Party’s chances in the midterm elections and fears that renewed fighting will lead to casualties that will do even more political damage to the administration.
But he also has to know that if he concludes a deal with Tehran about its nuclear program, then he will have to endure the sort of criticism that will infuriate him. Both his opponents and some allies will say—and not without justice—that he fought a war, but then settled for an accord that was little different from the one concluded in 2015 by former President Barack Obama, which Trump had bitterly criticized as dangerously inadequate.
Why was the war fought?
Indeed, if he ends the conflict with not only the Islamist terrorist government still in place, but ultimately strengthens and enriches it via relaxed sanctions and billions in released frozen funds, then it will be reasonable to ask why the war had to be fought. It will also be fair game to ponder what happened to the bold leader who had ordered strikes on Iran in June 2025 and again earlier this year, while demanding the “unconditional surrender” of a dictatorial Islamic regime that has been at war with the United States since it came to power in 1979.
At this moment in time, no one knows what Trump will decide to do. It may be that his decision to respond to the latest provocations by Iran, which shot down a U.S. helicopter in the Persian Gulf, and that of Hezbollah, which continues to fire on Israel from Lebanon, with “proportional response” rather than with a resumption of the war, will render a judgment on the fate of his presidency. It could be an indication that this is not the Trump who prided himself on his unpredictability and willingness to flout the conventional wisdom of the establishment he despises, which has warned ad nauseam that the war was certain to end in failure.
At this point, we might do well to consider how Trump made a very different yet equally important decision in his first term.
In David Friedman’s memoir Sledgehammer, the former U.S. ambassador to Israel recalled a crucial meeting in the White House situation room in November 2017. At this gathering, Friedman was confronted by opponents to his effort to move the U.S. embassy in Israel from Tel Aviv to Jerusalem—as Trump had promised to do—from his main foreign-policy advisers. U.S. Secretary of State Rex Tillerson, Secretary of Defense James Mattis and National Security Advisor H.R. McMaster all stood against the move, while the less formidable trio of Friedman, Vice President Mike Pence and U.S. Ambassador to the United Nations Ambassador Nikki Haley were in favor of it.
Trump’s vision of himself
As Friedman tells the story, after exposing Tillerson’s ignorance about the subject and illustrating that Mattis misunderstood where capitals belonged, he turned to the president and told him that “the world is watching.” What they were looking to see was “whether you are truly the courageous leader you claim to be, or just another politician who gets cold feet and breaks a promise.”
He added that the issue will “reverberate in Iran, North Korea and anywhere else America is challenged.”
That was all Trump needed to hear. The ambassador had read the president perfectly.
He might be persuaded to temporize and break a promise if he thought it was prudent. But the thought that people might not think that he was the decisive leader who was unafraid to tell off the foreign-policy establishment was intolerable.
Friedman noted that after a “few seconds of awkward silence,” Trump simply replied: “Of course, that’s right. Let’s do it.” He then exited the room, the crucial decision having been made, leaving Tillerson, Mattis and McMaster in a state of consternation.
The current Iran dilemma is not exactly analogous to the decision to move the embassy, though the thread linking them to each other is rooted more in Trump’s vision of himself than in the specifics of the policy implications.
In one sense, Trump took a tremendous risk deciding to go to war against Iran alongside Israel. The naysayers proclaimed that it was certain to fail. More than that, his political opponents were also in favor of returning to the appeasement of Iran pursued by Obama and former President Joe Biden.
Trump had rightly understood that the nuclear deal that was Obama’s signature foreign-policy accomplishment was not merely weak but a disaster for several reasons.
First, it did not prevent Iran from getting a nuclear weapon; it merely kicked the can down the road. The restrictions on Tehran’s nuclear program were due to expire by the end of the 2020s, meaning that it actually guaranteed that the Islamists would eventually get such a weapon with Western acquiescence.
On top of that, the relaxation of sanctions and release of frozen funds meant that Iran was enriched and empowered, and thus able to use that financial windfall to better finance its terrorist proxies and further their efforts to achieve regional hegemony. When Trump pulled the United States out of the agreement in May 2018, it was, by contrast, a terrible blow to Hamas in Gaza and Hezbollah in Lebanon. There was a chance that Trump’s “maximum pressure” campaign might have eventually succeeded had he been re-elected in 2020. Instead, when Biden became president in 2021 and resumed appeasement, Iran was again rewarded with funds. One can draw a direct connection between that and the war against Israel that was begun with the Palestinian Arab atrocities committed on Oct. 7, 2023.
When Trump returned to the presidency for his second term, he approached this question with the sort of sober analysis that the so-called adults who conducted Obama and Biden’s foreign policy lacked. He seemed to know that the Islamist fanatics who ran Iran would never stop until they achieved their nuclear ambitions, something that would not merely endanger Israel but place the entire region—and perhaps, America—under a deadly threat.
Trump strikes, then falters
That’s why Trump gave Israel a green light for the 12-day war on Iran last summer, ordering devastating American strikes on the country’s nuclear facilities. And after Iran chose to try and rebuild its program—moving quickly to increase their supplies of ballistic missiles that threaten its neighbors and the West—Trump decided to strike it again on Feb. 28, jointly with Israel.
These new strikes achieved great success in destroying Iran’s military, further damaging its nuclear and missile programs, and eliminating much of its leadership. But it was never going to be a war that could be won merely by airstrikes. And once Iran threatened shipping in the Straits of Hormuz—sending fuel prices up around the world—it achieved some leverage over the United States. That could have been removed by an American takeover of the key areas where Iran was blocking sea traffic, but that was a potentially risky move and something Trump was unwilling to do.
He responded with a highly effective blockade of Iranian ports that has the potential to eventually collapse the Iranian economy. But with his poll numbers dropping precipitously because of the unpopularity of the war and the increase in gas prices at the pump, he also agreed to a ceasefire with Iran and initiated diplomatic talks conducted by Middle East envoy Steve Witkoff, and his adviser and son-in-law, Jared Kushner.
Since then, the fighting has occasionally flared. Yet it has done so without the United States drawing conclusions about Iran’s seriousness in agreeing to Trump’s demands about giving up its nuclear program, let alone ending the missile threat or its terrorism. Worse than that, Trump has seemingly acquiesced to Iran’s demand that Israel halt its efforts to prevent Hezbollah from firing on the Jewish state. That revived the terrorist group’s role as Tehran’s protector and ally that had seemed to be neutered by Israel’s smashing victories over it in 2024 and 2025, as well as the collapse of the allied Bashar Assad regime in Syria.
And by conducting “proportional” attacks on Iran, Trump is behaving like the sort of president he claims not to be. Such measures, which are ineffective by definition, resemble those undertaken by the Johnson and Nixon administrations when they were trying to craft a peace deal that would allow them to exit Vietnam. The North Vietnamese understood these half-hearted measures as a sign of weakness, not strength. And unfortunately, the Iranians may be drawing the same conclusions about Trump, a development that bodes ill for his ability to get a deal on terms that would actually advance U.S. interests rather than those of Iran.
Witkoff and Kushner’s terms
The conditions that Witkoff and Kushner have been pursuing are no secret, with the pair or their aides likely being the source of leaks with the details to hostile publications like The New York Times.
For those who looked to Trump as someone who, unlike his predecessors, basically understood the nature of the regime that he was fighting, the accounts of the deal that he claims to be close to concluding make for sobering reading.
The Iranians are unlikely to fully agree to Witkoff and Kushner’s conditions. As they have done in the past with equally foolish negotiating partners, they will draw out the talks and demand concessions from diplomats who, as was the case with Obama’s diplomats, are desperate for a deal. Even if they signed on to what the Times claims are Trump’s terms, they are only marginally better than those in Obama’s Joint Comprehensive Plan of Action (JCPOA), with the promise of snap inspections and the dismantling of nuclear sites being the major improvements.
Yet the basic premise of a Trump Iran deal would be the same as Obama’s. It would, as the Times rightly points out, be as completely dependent on Iranian cooperation as the JCPOA. And anyone who thinks they will fully cooperate with the United States on this and not cheat on a new deal, as they did on the old one, has learned nothing from the past two decades of behavior from Tehran.
The new deal only makes sense if the Americans believe that Iran is more desperate to repair its economy and engage in global commerce than it is to pursue its Islamist terror goals. Obama believed that its leaders wanted a chance to “get right with the world” and get richer. Witkoff and Kushner apparently believe the same, and are thus willing, like Obama and his Secretary of State John Kerry, to agree to a 15-year moratorium on Iranian nuclear activity rather than its end.
Handing a victory to Tehran
Perhaps some in the administration think that the damage done to the Islamist government during the last few months of fighting is such that peace and the necessity of rebuilding so much of its infrastructure will undermine it to the point where it might fall. Such an assumption ignores the essential nature of the regime, which is a toxic combination of fanatical Islamism, corruption and bloodthirsty tyranny. As with past relaxations of sanctions and unfreezing of funds by the West, peace is far more likely to strengthen the Islamic Revolutionary Guard Corps, which essentially now runs the country, rather than weaken it.
The arguments for ending the war on even these dismal terms may seem persuasive to some in the administration and the GOP who are desperate for oil prices to fall. Vice President JD Vance, a war skeptic whose neutrality about the Jew-hatred spewed by his podcaster friend, former Fox News host Tucker Carlson, makes him eager to promote peace with Iran on virtually any terms. He has been claiming that the proposed deal is a “home-run win for the American people.”
There should be no illusions, however, about what this means for the Middle East or Trump’s presidency.
A deal on the terms that are being discussed will mean that Iran won the war that began on Feb. 28, no matter what Trump might say about it. It will mean that Washington will be essentially propping up one of its chief enemies on the world stage without really ensuring that Tehran won’t get a bomb in the long run or prevent it from spreading terror or threatening its neighbors with missiles.
That’s bad for Israel, Saudi Arabia and other Gulf states. But it will also be terrible for Trump, since a deal that is obviously a gift to Iran won’t undo the damage done by the war to his popularity or the Republicans’ chances in the midterms. The only thing that will reverse that trend would be a decision to take the risk of continuing the war. The United States should not let up on the military and economic pressure it can bring to bear on Iran until the regime is defeated or does actually surrender its ability to pursue nuclear weapons, missile production or terrorism.
That is something that the Donald Trump who defied the foreign-policy establishment and moved the embassy to Jerusalem—not to mention many other decisions that similarly infuriated the “expert” class but which proved to be right—might have done. But a Trump who listens to Witkoff and Kushner is not only someone who doesn’t understand the enemy he’s been fighting, but who lacks the will to go with his gut regarding moves the establishment decries.
It’s still possible that tough-minded Trump will wake up to the trap that he’s fallen into and reverse course. But unless he does, the taunts of Obama supporters about a new Iran deal being no better than theirs will be both painful and largely accurate.
Jonathan S. Tobin is editor-in-chief of JNS (Jewish News Syndicate). Follow him: @jonathans_tobin.
