Trump’s war with Iran is filled with flaws worsening things

June 28, 2026, 4:30 a.m. ET

The war with Iran that President Donald Trump and Israeli Prime Minister Benjamin Netanyahu partnered on is now entering its fifth month. Iran is a wreck. But so is the relationship between America and Israel.

Iran probably sees that as a victory on its own.

A flawed war plan that predicted a swift victory now pits Trump’s short attention span and aversion to accountability against Netanyahu’s continuing quest to topple Iran’s regime and desperation to hold sway over voters ahead of the next Israeli election.

To gauge the impact of the war on that relationship, I spoke to leaders of two American pro-Israel groups. Those interviews, conducted on June 26 while both men were in Israel, showed shared concerns about the relationship and the shaky “memorandum of understanding” (MOU) that Trump agreed to with Iran, without Israel’s participation.

Even so, they had very different ideas about how to proceed.

The Iranians are ‘mocking’ President Trump

Ilan Goldenberg, senior vice president and chief policy officer at the progressive, pro-peace group J Street, told me that Trump’s MOU with Iran is a bad deal, but that continuing the war was worse.

Michael Makovsky, CEO of the more hawkish Jewish Institute for National Security of America, is a critic of Trump’s MOU and thinks the war should continue until Iran’s nuclear program is eliminated and the Strait of Hormuz is fully open to traffic.

Makovsky, who spoke to me after being part of a delegation that met with Netanyahu on June 22, said public feuding between American and Israeli officials “only boomerangs against us” and benefits Iran.

Polls show that support among Americans for Israel is falling, and that Netanyahu is increasingly unpopular in this country.

Trump has confirmed recent reports that he profanely berated Netanyahu as the partners in war failed to remove the Iranian regime and instead created economic stress in America and around the world.

And Vice President JD Vance, in a not-so-veiled public threat, cast America as Israel’s only international friend and supporter after Israeli National Security Minister Itamar Ben-Gvir objected to the MOU in a social media post.

“It’s a little mind-boggling, frankly, and obviously strategically damaging to the United States to have these public spats when President Trump does it, and obviously it’s really stupid if any Israeli official does that as well,” Makovsky said.

The Iranians, Makovsky added, “are effectively mocking President Trump” by denying the terms of the announced agreement and continuing to attack ships in the Strait of Hormuz. America’s relationship with Israel can be further strained by a “strategically feckless” resolution that leaves Iran’s regime in place, doesn’t address nuclear concerns and allows for Iranian control of the strait, he said.

How did we get to this war with Iran?

Netanyahu has lobbied American presidents for years to partner in a military attack to wipe out the repressive regime in Iran. He sold the war with Iran to Trump in a February meeting in the White House’s Situation Room.

But Goldenberg, from J Street, told me the start of the fracturing between America and Israel came a decade ago, when then-President Barack Obama negotiated a 2015 nuclear deal with Iran that outraged Netanyahu, who then aligned himself with American Republicans who opposed the deal. Democrats, who had been widely supportive of Israel, began to peel away.

Now the war with Iran has concerned independents who supported Trump because of his campaign pledge to stay out of foreign conflicts, Goldenberg said, and may well “start a conversation inside the Republican Party” about our relationship with Israel.

He pointed to right-wing influencers ‒ Tucker Carlson, Megyn Kelly and former U.S. Rep. Marjorie Taylor Greene ‒ as starting that conversation, and Vance’s criticism of Netanyahu’s Cabinet as part of it.

One likely result of that: an end to what Goldenberg called the “blank check support” America provides Israel.

The United States was the first country to recognize Israel as a new nation in 1948. The Council on Foreign Relations in 2025 reported that Israel has received more than $300 billion in economic and military assistance ‒ adjusted for inflation ‒ from America.

A 10-year agreement between America and Israel, signed in 2016 as Obama was finishing his second term, provided for $3.8 billion in funding for Israel per year, which the White House called “a significant increase” at the time.

Goldenberg told me he doesn’t think that deal will be renewed when it expires in 2028. And he predicted that America will scale back on providing Israel with offensive weapons, sticking instead with “Iron Dome” missile defenses, especially if Democrats make big gains in November’s midterm elections and win the White House in 2028.

Iran emerges from the war bloodied and broken ‒ but also with sanctions on lucrative oil sales lifted, the prospect of a $300 billion reconstruction fund, billions more in frozen assets being released, and the potential for future tolling of ships in the Strait of Hormuz.

Goldenberg, who worked on Middle East issues at the Department of State and the Pentagon, said the long-term scenario always discussed to be avoided was a region with “Iran still in power, weaker, angrier, more dangerous, with the U.S. stuck managing a messier, more unstable Middle East.”

That sounds a lot like where we are right now. And Goldenberg said new outbreak of hostilities will create “more backlash” as Trump’s administration will need to “tamp Israel down” from aggressive retaliation.

At this point, America’s best prospect is for conditions in the Middle East to just return to how they were before Trump and Netanyahu started the war four months ago. That seems unlikely, since Iran has successfully frustrated the partners in war and has no reason now to stop.

The tension that creates seems like it will inevitably drive America and Israel further apart, a victory Iran might not have expected but will certainly celebrate.