Trump’s Iran Gamble Is Catching Up with Him

James Durso • January 26, 2026

• Donald Trump publicly encouraged Iran’s 2025 protests but then pulled back, leaving protesters feeling abandoned as Tehran cracked down.
• Years of U.S. policy reversals—from exiting the Joint Comprehensive Plan of Action to renewed “maximum pressure” and military strikes—have hardened Iran.
• Any escalation risks a wider regional conflict, with Iran threatening retaliation against U.S. bases and energy infrastructure.

It seemed like a good idea at the time…

After protests against economic mismanagement broke out in Iran in December 2025, U.S. President Donald Trump encouraged the protestors: “Iranian Patriots, KEEP PROTESTING – TAKE OVER YOUR INSTITUTIONS!!!” and “HELP IS ON ITS WAY.” He threatened to attack Iran if the government executed any of the protestors. Tehran relented, and Trump replied, “I greatly respect the fact that they canceled [the executions].”

Iran’s top prosecutor then rebutted Trump and declared, “We have a separation of powers, the responsibilities of each institution are clearly defined, and we do not, under any circumstances, take instructions from foreign powers.”

Iranian protestors felt betrayed by Trump’s reversal, and one declared, “Trump is worse than Obama…He pulled the rug from under our feet.”

Iranian and U.S. officials traded barbs after the protests subsided, and Iran’s internet is still down, possibly for the government to install a firewall. Tehran announced it would seize the property of protestors to pay for the damages.

Iran’s Arab neighbors urged Trump not to attack Iran as they fear violent spillover, a surge in refugees, and economic dislocation; Israel asked the U.S. to pause an attack as it did not have sufficient interceptor missiles to fend off another Iranian attack.

The U.S. is building military forces in the Middle East as Trump decides whether or not to strike Iran or to respond if Iran retaliates to an American or Israeli strike. Or Trump may hope to motivate the protestors to rise up again, but will they take the bait?

How did Trump get into this position?

It started when, in October 2017, Trump “decertified” Iran’s compliance with the Joint Comprehensive Plan of Action (JCPOA), the “Iran nuclear deal” that Trump called “the worst deal ever negotiated,” even though the European Union (EU) and the International Atomic Energy Agency agreed Iran was meeting its commitments. In May 2018, the U.S. withdrew from the agreement and reinstated sanctions on Iran.

Trump may have really felt the JCPOA was a “bad deal”, but he was also likely motivated because the JCPOA was Obama’s deal.

Iran abided by the JCPOA for a year after the U.S. withdrawal, maintaining limits on enrichment and stockpiles while the EU tried to preserve the deal. After the U.S. re?imposed sanctions and Europe failed to deliver meaningful economic relief, Iran began incrementally breaching the agreement starting in May 2019 by exceeding limits on enriched uranium stockpiles, enrichment levels, and centrifuge numbers, ultimately moving far beyond JCPOA constraints by 2020–2021.

In 2020, U.S. presidential candidate Joe Biden promised to rejoin the JCPOA but failed to do so upon assuming office. Iran signaled it was ready to resume nuclear negotiations but the Biden administration wanted a “longer and stronger deal” that would update the 2015 deal to extend key nuclear restrictions for a longer period; impose stronger limits on Iran’s nuclear program and regional activities; and address issues not covered in the original JCPOA, such as ballistic missiles or Iran’s support for its allies. Ignored was the fact that the reason Obama’s project succeeded was that it was narrowly focused and wasn’t a grab bag of Western grievances against Iran.

After he returned to office in January 2025, Trump reimposed “maximum pressure” on Iran, and in June 2025 U.S. forces attacked and “obliterated” Iran’s nuclear research sites in Operation Midnight Hammer.

Trump may be stalling to get military units in place to attack Iran or, despite his claim his forces are “locked and loaded,” he may now know that an Iran op won’t be as easy as the abduction of Venezuelan leader Nichola Maduro now that Iran’s clerical regime is back in control. He may also be having second thoughts about Crown Prince Reza Pahlavi, who he said “seems very nice,” but may be the wrong horse, much as Ahmed Chalabi was for the U.S. in Iraq. He may also recognize it is incongruous to try to reinstall a hereditary monarch in the name of “democracy.”

And The Telegraph reports, “Iran’s military power made Trump think twice,” as Tehran’s missiles and UAVs reached most U.S. bases in the region. And the countries that host those bases have no interest in being a target in an Israeli-American war of choice against Iran just to help Trump restore his amour-propre, especially when they would prefer to normalize relations with the Islamic Republic.

Trump’s retreat was not unique for a U.S. president.

In February 1991, U.S. President George H.W. Bush called on “the Iraqi military and the Iraqi people to take matters into their own hands and force Saddam Hussein, the dictator, to step aside.” When Iraqis rebelled, the U.S. did nothing.

President Barack Obama did not support the 2009 Green Movement against the Islamic Republic, though he later admitted he made a mistake. In August 2012, Obama also claimed that Syrian government use of chemical weapons against rebels would be “a red line for us,” but did not follow through when they were used.

In January 2026, the Trump administration stood aside when the Syrian government moved against the U.S.-supported Kurdish-led Syrian Democratic Forces (SDF). The two sides signed a cease-fire that effectively dissolved the SDF and allowed the Syrian Army will take control of three eastern and northeastern provinces that are the location of the country’s oil and natural gas reserves.

Former United Nations weapons inspector Scott Ritter argues that Trump stalled attacking Iran as a deliberate move to dismantle a long-prepared regime-change operation involving Mossad, the CIA, and the war party in Washington, D.C. Trump’s aim was to make both sides expose their plans, though the Israelis lost the most as their network in Iran exposed itself and is being dismantled. There’s no way to tell if Ritter’s claim is true, but if it is, Trump will brag about it eventually.

There is a long, sad history of U.S.-Iran relations, two parties in an abusive relationship; each side considers itself not the sinner, but sthe inned-against. The history includes:

• The U.S.-UK sponsored coup d’état that ousted a populist prime minister who wanted Iran to take control of its oil resources (1953)
• The Iranian Revolution that ousted the Shah, a U.S. client (1978-1979)
• The 444-day hostage crisis (1979-1981)
• S. support for Iraq in the Iran-Iraq War (1980-1988)
• Iran involvement in the bombing of the Marine barracks and the American embassy in Beirut, Lebanon (1983)
• Operating Praying Mantis, U.S. attacks on Iran oil facilities (1988)
• The U.S. navy shootdown of Iran Air flight 655 (1988)
• Abandonment of the Iran-Conoco deal to develop offshore oil fields (1995)
• Naming Iran as part of the “Axis of Evil” just when an influential military leader mused, “maybe it’s time to rethink our relationship with the Americans.” (2002)
• Abandonment of the JCPOA (May 2018)
• Killing of General Qasem Soleimani, the influential military leader who suggested a rethink of “our relationship with the Americans” (January 2020)
• Killing of Iranian military leaders and nuclear scientists (June 2025)
• S. strikes on nuclear sites (June 2025)
• Assassinations of Iranian nuclear scientists (since 2010, likely at the hand of Israel and the Mojahedin-e-Khalq but likely with approval by the U.S.)
• S. sanctions against Iran (1979-2026)

Trump may feel he has to attack Iran, regardless of the consequences, which will mostly be suffered by people who are not American, to reestablish his credibility. Instead, he should think twice and go against the counsel of Israeli Prime Minister Benjamin Netanyahu and the American hawks and…do nothing. The Iranians will never believe he isn’t dissembling, so even honest outreach will move very slowly, though Trump’s envoy Steve Witkoff plaintively said, “‘Iran needs to change its ways,” a sure sign the administration doesn’t understand Iran.

Iran is rearming, and Foreign Minister Abbas Araghchi said Iran will fire “back with everything we have if we come under renewed attack.” The commander of the Islamic Revolutionary Guard Corps, Mohammad Pakpour, warned Washington against “miscalculation” and declared, “Our finger is on the trigger.” Iranian officials warned neighboring countries that if the U.S. launched strikes from bases in their territory, Iran would target those bases in retaliation.

Tehran hopes to disabuse Trump of any idea that attacking Iran will be like attacking Venezuela. Even if Trump signals an end to fighting, Iran may continue to escalate and embroil the U.S. in an extended fight in the Persian Gulf and split from its allies, at least up to the mid-term elections on 3 November 2026.

Iran’s neighbors pressed Trump not to attack Iran on the protestors’ behalf, and will do so again. A U.S. attack on Iran will cause Iran to attack regional infrastructure such as oil and natural gas facilities, airports, seaports, and power plants. Hydrocarbon exports via the Strait of Hormuz will be disrupted just when prices jump, depriving the Gulf states of extra revenue that will be captured by U.S. exports instead.

Former Israeli defense minister Avigdor Lieberman noted, “They [Iran] didn’t hit random places. They knew exactly where to aim,” and “The next confrontation will not look like the last one.” Lieberman admitted Iran did more damage to Israel than what was reported publicly, “I don’t want to go into details, it’s impossible to explain more now.”

If Iran’s next barrage of attacks on Israel is “longer and stronger” than its June 2025 counterattacks, there will be enormous pressure on Trump to escalate attacks on Iran, though this will seriously deplete U.S. weapons stockpiles, which are much reduced after the U.S. defense of Israel in 2025 (and may take eight years to replenish)

Russia and China are not obligated to defend Iran when it is attacked by the U.S. and Israel. Russia is busy in Ukraine, but it may send weapons and intelligence to Iran. China is in a more difficult position as a U.S.-Israel attack on Iran will threaten the USD400 billion China-Iran 25-year strategic cooperation agreement and the USD60 billion China–Pakistan Economic Corridor, a 3,000 km infrastructure network project, and the main plank of China’s Belt and Road Initiative. China’s credibility will be damaged if it does nothing so it will also send weapons and intelligence, but will not confront the U.S. directly. Beijing may also threaten political or economic consequences for any country that helps the U.S. and Israel attack Iran.

Afshon Ostovar speculates on a coup to remove Supreme Leader Ali Khamenei from power: “If the old guard is behind a successful coup, Iran’s next regime will probably remain theocratic at home but become less ambitious abroad. If younger officials take over, Iran will likely grow less religious at home but remain assertive internationally.” If the latter comes to pass, Iran will become Pakistan with hydrocarbons, a situation everyone in the region, save Israel, can live with. It will also be a loss for the U.S. war party if Iran is “still standing,” though Trump will claim he got rid of the ayatollah.

The worst outcome for the U.S. and Israel is an Iran-directed reorganization that keeps the country intact, instead of a breakup that would “frustrate the interests of Russia, China, and others,” per Melik Kaylan. The U.S. will still demand Iran give up its nuclear program, its missiles, and its allies, but the Iranian citizenry may want to keep them as a way to secure territorial integrity as they likely noticed no one is talking about attacking North Korea.

After the June 2025 U.S.-Israel attacks, many Iranians asked why the country lacked a nuclear deterrent. One person posted, “Over 430 people were brutally murdered in Iran since the start of the war. These people died because Iran did not have a deterrence, specifically nuclear weapons…This ridiculous and completely uneducated fatwa is what helped murder these people.” If that sentiment survives another attack that causes the removal of the ayatollah (and his anti-nuclear fatwa) Iran may engage in a “redoubled effort” to go nuclear and America may be in the position of opposing defense programs with wide popular support. So much for democracy and vox populi.

Popular support for a nuclear deterrent is bad news for the Israelis and their American collaborators, and Crown Prince Pahlavi and his entourage, though Trump will move quickly to take credit for getting rid of “the turbans” and freeing the Iranian people (Iranians are generous people and will probably let him roll with it.) If that comes to pass, Iran’s new civil-military leadership gives the clerics “an offer they can’t refuse,” that is, adopting the “Najaf model” where clerics have recognized authority but stay out of politics and governance.

Trump’s real strategic interest is keeping the Republicans in charge in Congress, and that is more important than anything that happens in Iran. Trump wants a decisive attack option with little risk of U.S. casualties. Iran’s goal is to expand the conflict to split Washington from its allies and to kill Americans, so the Republicans lose the mid-term elections, and Trump is then too busy fighting the Democrats to fight Tehran.

Greg Priddy of the Center for the National Interest notes U.S. air and missile strikes are “not suited to degrading the main pillar of regime cohesion, which is the rank and file units of the Islamic Revolutionary Guard Corps (IRGC) and Basij [militia].” Though Trump claimed Iran’s nuclear program was “obliterated,” he may reattack the surviving nuclear facilities and the “missile cities” that are in all provinces of Iran. That will require an extended air campaign that risks American pilot POWs, and we will then have “America held hostage” all over again, but without the $39.50 per barrel oil.

And Trump will be the new Jimmy Carter.

Trump will not want to “chicken out” so he may default to a limited attack and then claim he “taught them a lesson they won’t soon forget!” while the Iranians claim they drove off the Zionist and American aggressors. According to prediction market Polymarket, there is a 17% chance the U.S. attacks Iran by 31 January 2026; only a 3% chance Khamanei will be ousted by the end of that month; and a 65% chance the U.S. attacks Iran by the end of June.

A limited Iranian retaliation may be against the U.S. troops based in Iraqi Kurdistan, and that will serve two purposes: strike the Americans, and discipline the Kurdish leaders who may have been aware of the attempted infiltration of Iran by Kurdish separatist forces from Iraq in the early days of the protests. (The infiltration was foiled when Turkey tipped Iran of the infiltration.) Baghdad may only register a pro forma complaint to Washington, especially after the recent U.S. threat to “starve” Iraq of oil revenue if political parties the U.S. considers friendly to Iran are in the new government.

Priddy notes that if America forgoes a decapitation attack against Iran’s leadership, the Iranian response may be measured, as it will also want to preserve relations with its neighbors. Trump’s challenge will be keeping the Israelis onside and limiting their assault to America’s preferred targets.

For Trump, there is no “easy button” for Iran, and whatever his response, it must not make things worse in the region. A political resolution between Tehran and Washington will have to await a new U.S. president, given the mistrust Trump sowed by leaving the JCPOA.

(Republished from Oil Price by permission of author or representative)

https://www.unz.com/article/trumps-iran-gamble-is-catching-up-with-him/