Unfair play! Trump prefers to make big moves during "market closures." Is he going to "harvest" again this weekend?

From midnight operations to weekend threats, the kind of “no rules followed” surprise attacks by Trump not only have Wall Street traders walking on eggshells, but are also thoroughly reshaping the playbook of the game between Washington and financial markets.

U.S. President Donald Trump is used to bombarding people with all kinds of messages around the clock, but his recent sharp shift in stance on the Iran issue makes one thing clear: he often saves his biggest chips for when the market is closed.

On Saturday night in U.S. Eastern Time, Trump announced that Iran would have 48 hours to reach an agreement, or else its utilities and other critical infrastructure would face a wave of devastating strikes. However, just after 7 a.m. on Monday, he canceled that action. Although this back-and-forth tightrope—only temporary—has managed to curb a potential wave of market sell-offs and ease pressure in the oil market. And within minutes after the closing bell rang on Thursday, Trump again extended the deadline to April 6.

As a result, traders across the stock market, fixed income, and commodity markets are now increasingly reluctant to make big bets ahead of the weekend. Given that various asset classes may see wild swings when markets open next week, staying in cash over the weekend can effectively reduce the risk they face.

This is no different from Trump’s familiar playbook of staging a “shocking Saturday” stunt: his June strikes on Iran, his “great job” actions in controlling Maduro, and the Iran mission he has recently launched were all carried out on Saturdays and throughout the weekend—at a time when major global markets, including foreign exchange, are closed.

The drivers behind each major announcement are different. His allies insist that even though Trump knows market dynamics inside out, he makes every decision strictly on its own merits. Even when viewed with the most discerning lens, it’s clear that different market factors are influencing Trump: sometimes he acts only after the market has been hit by sell-offs; sometimes he moves in a preemptive effort to prevent an expected crash; and sometimes he’s simply making time for traders to digest major moves that could change the world order.

But Trump’s preference for these dramatic actions, along with his track record of causing trouble specifically during market-closed periods, has already rewritten the rules of the game between Wall Street and Washington. As the real-world impact of the blockade in the Strait of Hormuz continues to intensify, his ability to calm markets with polished talk is steadily weakening. Even when Trump announces a pause of 10 days for certain strike actions, no one dares to guarantee he will follow through.

Kathy Jones, chief fixed-income strategist at Charles Schwab?—this week said, “Entering the weekend with any position means taking on a tremendous amount of risk when Monday morning comes.”

Trump just likes making big news when markets are tense

A theory that’s widely circulated, built by Deutsche Bank strategists led by Maximilian Uleer, suggests: Trump often makes moves when market pressure appears at its highest.

Deutsche Bank’s “pressure index”—which takes into account the performance of the S&P 500 index and U.S. Treasury yields, inflation expectations, and Trump’s approval rating—shows that before Trump decided to delay last spring’s so-called reciprocal tariffs, clarify that he does not plan to fire Federal Reserve Chair Jerome Powell last summer, and the threat earlier this year of using force to seize Greenland, the index had been surging. Currently, the index is at the highest level since Trump took office in January 2025.

There is also evidence suggesting Trump’s weekend actions create violent swings for investors when the markets open on Monday, leaving them with almost no chance to quickly unwind the orders that went the wrong way. Take two major markets as examples: the EUR/USD exchange rate and the S&P 500 index. Their Monday opening prices have become increasingly often much higher than—or much lower than—their Friday closing prices. Traders call this phenomenon a “gap-up” or “gap-down.”

“I think it’s reasonable for everyone—whether it’s the markets or regular people like us—to expect more volatility over the coming weekends,” Josh Lipsky, chair of international economics at the Atlantic Council, said. But he also warned: “Some signals are indeed hidden in the noise, but we shouldn’t overinterpret them.”

The White House said it did not intentionally time military actions to coincide with market closures, but it did not directly respond to Trump’s remarks last weekend.

“Somehow people have come to think that the timing of these military actions is based on when the stock market is closed, rather than on the best operational window for intelligence recommendations and mission success. That idea is utterly ridiculous—only someone who has never even planned a kid’s birthday party would believe it,” spokesperson Kush Desai said in a sharply worded statement sent via email.

As Trump takes his latest steps, the U.S. military continues to assemble in the Middle East or move toward the region—intensifying concerns that the U.S. may take new actions or that the situation could potentially escalate, such as seizing the key export hub, the island of Harkle, which Trump has previously repeatedly touted as not having had its oil infrastructure destroyed.

In addition, the frenzy in which these major headlines were released has also sparked questions about insider trading, including precise bets made minutes before Trump issued the announcement.

The weekend military actions themselves also brought logistical challenges. For example, when Trump was directing some of the most significant military missions involving his government, he wasn’t sitting in the Oval Office or the White House war room—instead, he was operating from a temporary secure facility at his Mar-a-Lago estate in Florida.

A White House official who asked not to be named said many of Trump’s most significant moments happened to fall on weekends, which was purely coincidental, with other factors certainly at work behind the scenes. Trump has said that the strike against Maduro was postponed by several days to wait for good weather, and only at around 4 a.m. on Saturday did he pull the trigger. And last June’s “Midnight Hammer” operation is said to have been partially because Saturday is the Jewish Sabbath, maximizing the element of surprise.

“Given other conditions equal, I’m sure decision-makers would tend to minimize market turbulence, but mission success and the safety of the personnel executing the mission weigh far more,” said Victoria Coates, vice president at The Heritage Foundation and a former Trump national security adviser. “I don’t think ‘market-closed weekends’ would be the main driver.”

Even so, Trump does not hide his desire to soothe markets even in times of crisis. On Monday morning, after he abruptly issued a statement, the oil market reacted with relief. In addition, Trump also praised the exceptional ability of Treasury Secretary Bessent to contain negative effects.

Bessent’s “comfort pill”

“He runs the money bag in this country. You know, as soon as he goes on television, he can put a comfort pill into everyone’s mouth,” Trump said earlier this month about Bessent.

The Treasury Secretary regularly appears on early-morning television interviews before U.S. stock markets open. He is also a frequent guest on Sunday morning news programs, repeatedly communicating the areas he believes the market should focus on. Just last Sunday, on NBC’s “Meet the Press,” he emphasized that energy prices, after the current conflict ends, would “return to reasonable levels.”

However, Trump’s actions on Monday—something Tobin Marcus of Wolf Research dubbed “Schrödinger’s TACO (Trump always backs down)”—still leave a key unanswered question: are the negotiations with Iran a genuine possible escape route, or did Trump merely pause the most intense attacks during this trading week to stabilize the situation, planning to reignite hostilities again next weekend?

In a report on Monday, Marcus warned investors that as Trump sends more Marine Corps units to the region, the risk of escalation remains high, increasing the likelihood that the U.S. military could seize Harkle Island. “When this force arrives, Trump will face a choice: to give ground, double down, or muddle through,” he wrote. “We think this decision won’t be easy to make, but we’re confident investors must take seriously the possibility of escalation.”

Trump continues to release confusing signals about his true intentions. Just a few hours before he pushed back the deadline on Thursday, he even questioned Tehran’s willingness to reach an agreement.

“That could be a delaying tactic until our troops are deployed,” Wendy Sherman, former U.S. Deputy Secretary of State, said. “But if that’s indeed the case, then the United States must be prepared for a long, drawn-out tug-of-war—and the president can’t forever freely control the market’s pulse every Saturday and every Monday morning.”

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