Trump Hits the Stalemate Phase of His International Interventions, and It Stings

News Analysis

Trump Hits the Stalemate Phase of His International Interventions, and It Stings

 

In Ukraine, Gaza and now Iran, President Trump’s early declarations of easy wins have given way to harsh reality.

 

David E. Sanger

By David E. Sanger

David E. Sanger has covered five American presidents over four decades at the Times, and writes often on the revival of superpower conflict, the subject of his latest book.

https://www.nytimes.com/2026/05/31/us/politics/trump-iran-stalemate-ukraine-gaza.html

May 31, 2026

 

President Trump likes his military and diplomatic victories quick, clean and decisive.

 

On his desk in the Oval Office, he keeps models of the B-2 bombers that took out three Iranian nuclear sites in one night, not quite a year ago. In the opening weeks of the Iran conflict this year, he talked often about replicating his success in Venezuela — “the perfect scenario,’’ he said — shorthand for overthrowing a troublesome leader with one quick commando raid, and replacing him with a pliant, American-friendly successor.

 

But now, Mr. Trump has hit the stalemate phase of his presidency.

 

The war with Iran is clearly at that stage. When he declared a cease-fire on April 7, Mr. Trump said on social media that the end of combat operations would be conditional on “the COMPLETE, IMMEDIATE, and SAFE OPENING of the Strait of Hormuz.” It wasn’t. Even if commerce now resumes across the strait under a memorandum of understanding still under negotiation, it will still leave the future of Iran’s nuclear and missile programs exactly where they were in February: stuck in a further negotiation that the administration insists will be “time limited,” probably to 60 days.

 

But the Iranians sense Mr. Trump’s deep reluctance to restart combat operations that are deeply unpopular in the United States, and most Iran experts say they expect Tehran to try to stretch the negotiations for months or years — as they have with past administrations.

 

Then there is the Ukraine war, a conflict in its fifth year that Mr. Trump famously boasted he would end in 24 hours after taking office. Sixteen months after he was sworn in, he rarely mentions the war anymore, and Secretary of State Marco Rubio recently complained that he was tired of wasting time in endless negotiations, suggesting that he would be perfectly happy if some other country wanted to step in and play that role.

 

For their part, the Russians have quietly made clear that they are tired of periodic visits from the president’s special envoy Steve Witkoff and Mr. Trump's son-in-law Jared Kushner, according to people familiar with the negotiations. They say they want a stable, diplomatic process, with working groups and regular meetings. They also want an American ambassador to Russia — a job that has been open, astoundingly, for nearly a year.

 

And there is Gaza. When Mr. Trump flew to Israel to celebrate the release of the last of the living hostages from the Oct. 7, 2023, terror attack, he enthused about a 20-point plan that started with the disarming of Hamas, the creation of an international stabilization force and, ultimately, rebuilding Gaza into a gleaming territory of glass office towers and seaside resorts. Eight months after that trip, Hamas has still not disarmed, except in fake, A.I.-generated videos. (One, sent out by Mr. Trump, depicts him and Prime Minister Benjamin Netanyahu sunbathing.)

 

While more aid is making its way into the territory, Palestinians are still sleeping in tents, the rat-infested rubble has not been cleared, and Mr. Netanyahu announced last week that the Israeli military would expand its control to about 70 percent of the Palestinian enclave.

 

Perhaps all of this is the inevitable result of a president with huge ambitions running into the brick walls of global realities. Perhaps it is the result of overreach, as Mr. Trump — infused with the success of his first two military adventures, into Iran and Venezuela — assumes that there is no task too big for the U.S. military.

 

Some experts suggest that it arises from a fundamental misunderstanding of American power. As one of Mr. Trump’s close aides said recently, destroying nuclear sites from the air is what America does best, and controlling political events in nations like Iran, Russia and Ukraine is what the United States does worst.

 

“Foreign policy tends to be a long and difficult enterprise,” Richard Fontaine, a former top aide to Senator John McCain and now the chief executive of the Center for a New American Security, said in an interview over the weekend. “Mr. Trump is not the first president to imagine quick, simple solutions to complicated and enduring international problems. Yet it is the sustained management and follow-through that often makes all the difference, not the grand and dramatic announcement.”

 

Follow-through has never been Mr. Trump’s strong suit. To establish his bona fides for a Nobel Peace Prize, he liked to gather testimonials to the breakthroughs he made or invite leaders at the White House and hold a signing ceremony; if fighting resumes, he is unlikely to dwell on the implications.

 

An exception is the Russia-Ukraine conflict, where Mr. Trump has episodically admitted he underestimated the complexity of the problem, and perhaps his powers of persuasion.

 

“I’ve had cases where I had Putin all done and Zelensky wouldn’t make the deal, which shocked me,” Mr. Trump said in an interview with The New York Times in January, referring to Presidents Vladimir V. Putin of Russia and Volodymyr Zelensky of Ukraine. “Then I’ve had cases where it was the reverse. I think now they both want to make a deal, but we’ll find out.”

 

In the nearly five months since that interview, Mr. Trump has repeatedly predicted a deal was near, and repeatedly it has fallen through. Today the Ukrainians feel more empowered. Their long-range drones and homemade missiles are reaching deep into Russian territory, striking critical energy sites, factories and laboratories that churn out key weapons components, and occasionally targets in Moscow. One of Britain’s intelligence chiefs, Anne Keast-Butler, said last week that nearly half a million Russian soldiers had been killed in a conflict that Mr. Putin thought would be over in weeks.

 

Yet Mr. Rubio, who left the negotiating chiefly to Mr. Witkoff and Mr. Kushner, sounded the other day as though he had given up on moving either side to a peace accord anytime soon. “The U.S. stands ready and prepared to help do whatever we can to help facilitate the end of this war,” he told reporters on Tuesday. “And hopefully the opportunity will present itself at some point that we can play that role again.”

 

To some experts who have been playing a behind-the-scenes role in trying to spur negotiations, the administration’s mistake has been relying too much on episodic phone calls or visits of special envoys, without the day-to-day engagement of traditional diplomacy to keep talks moving.

 

“This conflict is ripe for conclusion,” said Thomas Graham, a longtime American diplomat who served in Moscow before the collapse of the Soviet Union and managed a strategic dialogue with the Kremlin during the George W. Bush administration. “The mood has changed in Moscow. The battlefield is different: The Ukrainians have frozen the front line. The economic problems in Russia are building, and some political discontent is bubbling up. Conversations inside the Kremlin are on ‘How do we present this as a victory?’”

 

But he noted that “you have to have a negotiating process,” and that is still missing. “I think they would like to see the process institutionalized,” Mr. Graham added, “so it’s more than a couple of envoys talking to Putin.”

 

Iran is a particularly complex form of stalemate.

 

During the negotiations with Iran in Geneva in February, Mr. Witkoff said in an interview with Fox News that Mr. Trump was “curious as to why they haven’t — I don’t want to use the word ‘capitulated,’ but why they haven’t capitulated.”

 

Mr. Trump asked the same question in the opening weeks of the war. He declared that the only outcome acceptable to him would be an Iranian “unconditional surrender.”

 

None of that happened. When I asked Mr. Trump, on his flight back home from China in the middle of May, why he thought resuming military action would bring him any closer to his political goals than the first round of strikes had, he erupted with a list of targets hit by the military, and pointed to a devastated Iranian air force and navy, but never answered the question of why Iran never gave up its enriched uranium or its missile program. He called the Times, and me, “treasonous.”

 

That was two weeks ago. Now Mr. Trump is trying a mix of incentives, threats and revised demands to force the country into the kind of negotiation that was underway in February, when he and Mr. Netanyahu initiated the war.

 

“He tried to bomb Iran, he tried to blockade Iran, he tried to bully Iran, and he is stuck,” Jake Sullivan, the national security adviser to President Joseph R. Biden Jr., and a key player in the Obama-era negotiations with the country, said recently.

 

Should Mr. Trump and Iran’s clerical and military leadership agree to the accord, that would start a new round of negotiations that could stretch on.

 

“The narrower problem of ongoing Iranian enrichment was solvable through bombing, at least in the medium term,’’ Mr. Fontaine noted. “The broader problem of the Islamic Republic is not.”

 

Mr. Trump ran into similar discoveries in Gaza. There, he successfully brokered a truce between Israel and Hamas, and all hostages, both dead and alive, were released. But everything after that has stalled, and Mr. Trump lost focus as the Iran conflict consumed attention.

 

A new Palestinian administration, which Mr. Trump suggested would be in place in months, has not entered the territory to take charge of rebuilding the cities. Mr. Trump’s “Board of Peace,” which was supposed to oversee the rebuilding and investment effort, has barely gotten out of the starting gate. And Israel continues bombardments almost daily.

 

David E. Sanger covers the Trump administration and a range of national security issues. He has been a Times journalist for more than four decades and has written four books on foreign policy and national security challenges.