On March 23, Trump announced a five-day pause in striking Iran's energy infrastructure, claiming that there had been "very good, productive dialogue" and "significant points of consensus" between the U.S. and Iran. Once the news broke, Brent crude oil fell from $112 to $99.94, plummeting 10.92% in a single day, the largest single-day drop since the launch of Epic Fury.

However, Iranian Speaker of Parliament Ghalibaf immediately denied that any direct negotiations were taking place. Turkey, Egypt, and Pakistan were acting as intermediaries relaying messages, while Kushner and Whitaker were coordinating, but there was disagreement about whether discussions were actually happening.

This is not the first time Trump has issued an "ultimatum" on the Iran issue only to retreat. From 2018 to now, similar patterns have occurred seven times.

7 Threats, 2 Fulfilled

Looking at all of Trump's major threats to Iran from 2018 to the present, the pattern is quite clear.

In 2018, he withdrew from the Iran nuclear deal and followed through, reinstating sanctions as scheduled. In February 2026, he launched Epic Fury, also following through, killing Khamenei within 24 hours and destroying over 70% of Iran's missile launchers (according to Israeli intelligence estimates). These two actions fully materialized, with oil prices reacting dramatically; Epic Fury sent Brent soaring from $71 to $119.50, an increase of 70%.

But the other side is equally notable. In June 2019, after Iran shot down a U.S. drone, Trump ordered strikes on Iranian radar and missile positions, with the military "cocked and loaded," only to call off the attack ten minutes before it was set to begin. On March 21, 2026, a 48-hour ultimatum was issued to Iran to reopen the Strait of Hormuz, and after the deadline passed, no strikes occurred; instead, a "five-day pause" was proposed.

Out of the seven instances, two were completely fulfilled, two were partially executed, two resulted in retreat, and one remains undetermined. Market reactions are also changing. Following the halt of strikes in 2019, oil prices only fell back 3-5%. This time, with a five-day pause, oil prices dropped directly by 10.92%. The market's reaction to "pause" signals is amplifying, as investors increasingly price in "threat depreciation" more quickly.

What Does $100 Oil Indicate?

Once the five-day window expires, there are three potential paths.

The first path involves reaching some sort of framework agreement. This would not be a comprehensive deal, but more likely a temporary freeze of 30-60 days to allow time for follow-up negotiations. In this scenario, Brent could fall back to the $80-90 range, approaching Goldman Sachs' average 2026 price forecast of $85.

The second path involves extending discussions. After the five days, if neither strikes occur nor agreements are signed, a new pause window may be created. Oil prices would likely remain volatile in the $95-110 range, with the war risk premium neither eliminated nor escalated.

The third path involves resuming strikes combined with continued blockage of the Strait of Hormuz. According to CSIS's scenario model, if Iran escalates attacks on Gulf oil facilities following strikes, Brent could skyrocket to $130-150. Goldman Sachs' extreme scenario is even more aggressive, forecasting that if the Strait of Hormuz is blocked for 60 days and Middle Eastern output is reduced by 2 million barrels per day, oil prices could exceed the historic high of $147 from 2008.

Currently, the pricing of Brent at $100 implies about a 30-40% probability of reaching an agreement. In other words, the market believes there is a 60-70% chance that the situation will not fundamentally improve after five days. If talks fail, oil prices could have an upside potential of $30-50.

35 Months in 2015

Trump's six core demands include zero uranium enrichment, dismantling nuclear facilities, a five-year freeze on missile development, stopping funding for proxy armed groups, recognizing Israel's right to exist, and a physical takeover of Iran's high-enriched uranium stockpile by the U.S. These demands far exceed the framework of the 2015 JCPOA. The agreement back in 2015 only restricted enrichment levels to 3.65%, allowed facilities to operate, and did not address missiles or proxy armed groups.

The JCPOA process began with secret contacts in Oman in July 2012 and culminated in a signing in Vienna, taking a total of 35 months. It underwent changes with the pragmatic rise of Rouhani, the establishment of trust through the interim Geneva agreement, and 20 rounds of direct negotiations among the P5+1 countries.

Where does the progress of 2026 stand? There was an indirect message relay from Oman on February 6, but then fighting broke out on February 28. By March 23, only 45 days had passed, and there was a lack of agreement even on whether "negotiations were occurring." The intermediaries consist of Turkey, Egypt, and Pakistan relaying messages, rather than the P5+1's multilateral direct negotiations. The prerequisite conditions for negotiations (both sides acknowledging that negotiations existed) have not yet been met, while in 2015, there was already over a year of trust established through secret channels before entering public negotiations.

What Cards Does Trump Have If Talks Fail?

The military card is the most straightforward. Strikes on power plants are the direct target of the five-day pause, and the operational threshold for resuming strikes is the lowest. More escalated options include blockades or occupations of Kharg Island, with reports from Al Jazeera indicating that plans have already been discussed as of March 20. Kharg handles 90% of Iran's crude oil exports, around 1.3-1.6 million barrels per day (according to EIA data). In terms of nuclear facilities, Natanz was already damaged in the first week of the conflict, and Fordow has not transferred high-enriched uranium since the strike in June 2025 (according to FDD analysis), but the new facility built by Iran under Pickaxe Mountain, 100 meters below a granite mountain near Natanz, is beyond the reach of air strikes. Currently, the U.S. military has deployed two carrier strike groups, over 16 surface ships, and more than 100 aircraft in the Middle East (according to Military Times), marking the largest scale since the 2003 Iraq War.

On the economic front, Trump announced in January that a 25% tariff would be imposed on countries doing business with Iran. The primary targets are China (which accounts for over 90% of Iran's oil trade), as well as India, the UAE, and Turkey. Iran's current oil exports still amount to about 1.5-1.6 million barrels per day, generating daily revenue of about $140 million (according to Defense News data).

Cyber warfare is already underway. According to Foreign Policy, prior to the kinetic strike of Epic Fury, the U.S. Cyber Command had initiated "non-kinetic effects," disrupting some of Iran's communication and early warning systems.

But Iran also has countermeasures. According to the U.S. Defense Intelligence Agency (DIA), Iran could maintain a blockade of the Strait of Hormuz for 1-6 months. The Strait sees 20 million barrels of crude oil and refined oil transit daily, accounting for 20% of global oil consumption (according to EIA data), while pipelines bypassing Saudi Arabia and the UAE have a capacity of only 3.5-5.5 million barrels per day, leading to a shortfall of up to 14.5 million barrels per day. Iran still has around 1,500 ballistic missiles and 200 launchers (according to Israeli military estimates), and Hezbollah possesses approximately 25,000 missiles (according to Israeli assessments).

This encapsulates the underlying logic of the five-day window's strategic game. Trump faces a credibility trap; if strikes occur, oil prices could spiral out of control, putting domestic economics under pressure. If strikes do not happen, the cycle of ultimatums and pauses will further undermine the pricing power of military threats. Iran's predicament mirrors this; if talks happen, hardliners domestically will not agree. If talks do not occur, the next round of strikes may target power plants and Kharg Island. The expiration date of March 28 is not an endpoint, but rather the next turn of this trap.

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