Responding to a taunt from an ally about his inaction on Iran, Trump asked: "How did going into the Middle East, how did that work out? And how did going into Iraq work out?"
Having broken the multinational denuclearisation deal with Iran, despite being warned by allies like Britain and Germany, Trump finds himself in the year before the presidential election with no carrots to persuade Tehran to back down but with a stick that he finds he can't swing as the US - and he - have little appetite for war.
It would also be devastating for the global economy teetering on the edge of a recession because it would disrupt energy supplies.
In essence, Iran holds global economy hostage and though weak compared to the mighty US, it now acts from a position of strength.
While Trump wants talks with Iran, Supreme Leader Ayatollah Khamenei has said that there won't be any, unless Trump removed the economic sanctions he has imposed on it.
Ever since the deal was scuttled and Trump piled on sanctions, Tehran has been ratcheting up the level of provocaton.
Iran has begun enriching uranium now as it considers the nuclear deal as dead.
Two oil tankers were attacked in the Gulf of Oman in June and Iran was blamed for it by the US.
Iran brought down a US drone in the area of the Strait of Hormuz in June and America was poised to strike back with missiles when Trump dramatically stopped it at the last month having realised the cost of Iranian retaliation and a slide to war.
Two Saudi oil facilities were attacked on September 14 disrupting about half the Kingdom's petroleum production.
The Tehran-backed Houthi rebels in Yemen, where the Saudis and the Iran have been locked in a proxy war, claimed they carried out the attacks.
But Secretary of State Mike Pompeo blamed Iran for it and called it an "act of war" putting Trump in a tight spot.
Trump was elected on a promise to cut foreign entanglements and bring troops home. But he had also swaggered in declaring he would be tough on adversaries and back Israel - and, less openly, other Middle East allies.
Now both those objectives are in conflict.
He tried in unprecedented ways to make a deal with the Taliban that would enable him to bring troops back home.
Playing the role of a peacemaker, he attempted to get North Korea to agree to curb its nuclear ambitions even as he was undoing the multinational deal with Iran end its nuclear programme that was heading towards weaponisation.
He was egged on by the hawks in his party, who underestimated Teheran, and by Prime Minister Benjamin Netanyahu of Israel and the royals of Saudi Arabia to break the Iran deal.
But Trump and the US hawks lacked lessons in the history of the region and the culture of Iran that could have warned them of the risks.
Iran suffered massive casualties and economic damages from the war with Iraq in the 1980s, but were unbowed, almost embracing the pain masochistically.
The punishing economic sanctions after the Iranian revolution of the 1970s, and before the nuclear deal left them undaunted, too.
Saudi Arabia now finds itself without a reliable protection from the US.
First of all, despite having spent billions in US arms it found itself vulnerable to Iran-made drones and low-flying missiles.
Secondly, the US seems unwilling to go to war on its behalf. The US is now self-sufficient in oil reducing an incentive to act and the killing of journalist Jamal Khashoggi along with human rights violations, especially of women, buys it no sympathy in the US.
With a population of 83 million, Iran is the biggest nation in the region capable of raising a formidable army of its own.
It wields outsize influence in Iraq and has its tentacles across the region, reaching into the borders with Israel.
Despite an investment of more than $150 billion in sophisticated weapons, Saudi is no military match.
It has had to rely on Pakistani instructors and at various times troops from that country have been stationed on its soil.
Israel's Netanyahu is facing uncertainties in elections and the country is in political turmoil. That limits the diplomatic pressure that can be exerted on the US to take on Iran. And although Israel can carry out pinpoint military missions against foes and has defeated several countries attacking it simultaneously, projecting its power all the way to Iran would be a stretch.
Pakistani Prime Minister Imran Khan has pledged his support to Riyadh during his current visit, his military can hardly be expected to defend Saudi Arabia. It has even refused get involved in Yemen on Saudis' behalf. And as Iran's neighbour, it is even more vulnerable.
The West European co-signatories of the nuclear deal - Britain, France and Germany - are powerless to meet Iran's demands that they disregard Washington's sanctions because of the US economic muscle. Even China has generally fallen in line with the sanctions.
That leaves only Russia with a degree of leverage with Iran with whom it has some degree of cooperation in Syria.
The US has tried to form an armada to protect the shipping in the Gulf, but they would hardly be able to do much if a large scale conflict broke out.
Trump will now have to work with Pompeo and his new National Security Adviser Robert O'Brien to work a way out of the standoff, either by de-escalation or a show of force that does not cause serious harm to the global - and US economy - endangering his re-election prospects.
(Arul Louis can be contacted at arul.l@.in and followed on Twitter @arulouis)
( With inputs from IANS )