Among the more surprising cheerleaders for President Donald Trump’s diplomacy with Iran were several progressive foreign policy analysts who had advised former President Barack Obama and former Vice President Kamala Harris. 

Now, many of those same voices — including Phil Gordon, Harris’ national security advisor who would likely have stayed in the role if she had been elected president last year — are expressing skepticism about Israel’s preemptive strikes on Iranian military and nuclear sites, and urging Trump to pressure Israeli Prime Minister Benjamin Netanyahu to cool it.

“I would have found it too risky to initiate military force with all that that could unleash,” Gordon told Jewish Insider on Friday. His approach would have been “to try to get an enduring, diplomatically-negotiated nuclear arrangement that prevented Iran from being able to get a nuclear weapon.” 

If he were advising Harris, or another Democratic president, Gordon would’ve wanted “to try to get that accomplished without having used this military action,” he said. 

Gordon also argued that Trump was manipulated into supporting Israel’s strikes by Netanyahu, even as Trump celebrated Israel’s killing of Iranian hardliners, noting that several of Trump’s senior advisors have urged restraint rather than intervention.

“His supporters did not put him in place to get involved in the conflict in the Middle East,” Gordon said. “A lot of his advisors … served in Iraq or are against U.S. military interventions in the Middle East. We know where Vance is in terms of intervention. The Tucker Carlson view, Don Jr. I think Trump really wanted to avoid military conflict and negotiate a deal and be the guy who got a better deal than Obama.” 

Ilan Goldenberg, who served as an Iran advisor at the Pentagon in the Obama administration and who advised Harris on Middle East issues during her 2024 campaign, told JI that Trump should try to encourage parties in the region to tone it down. 

“I think the appropriate position for the United States to be in now is the role of de-escalator,” said Goldenberg, now the senior vice president and chief policy officer at J Street. “The better option, the less risky option that had more good outcomes, was the diplomatic option. Unfortunately, it’s not the way it went. So now we have to see.” 

J Street released a statement on Friday calling for an end to the “cycle of retaliation and escalation,” and for a return to diplomacy between the U.S. and Iran. 

Both Gordon and Goldenberg questioned Israel’s end game in the strikes, which killed several senior Iranian military leaders and destroyed an above-ground uranium enrichment site at Natanz. 

“It definitely has set back the timetable for Iran’s nuclear capacity, but it hasn’t eliminated it, and we also don’t know what happens in terms of retaliation. We’d like to think and hope that Iran has been deterred and won’t respond in a way that we can’t handle,” Gordon said. “So far, so good, but we’re only on the first day, so there were real risks of doing it this way. And that’s why I would have sought, if at all possible, to do it a different way.” 

Goldenberg, who said the most important next step in stopping the violence is for the U.S. to help Israel defend against Iran’s retaliation, said he is unsure whether the Israeli success will turn into a long-term victory.

“The Israelis are incredibly good operationally, but they have challenges sometimes translating that into a strategic kind of sustainable victory, as opposed to just continuing to fight,” said Goldenberg. “What’s the end state here? What are you trying to do? Or is the objective to just be in constant conflict?”

Still, even as they said a return to diplomacy is the best way to move forward, both Gordon and Goldenberg acknowledged that Israel’s Friday attack on Iran had so far gone well for Israel.

“It is a remarkable display of Israeli military and intelligence capabilities,” said Gordon. 

“I think in the immediate [term], it had a lot of success. Very impressive operationally,” Goldenberg noted. 

Trump said in Truth Social posts on Friday that Iran could have a “second chance” at a deal, and that they should return to the negotiating table “before there is nothing left.” 

Goldenberg agrees — and he thinks Israel needs to hear from Trump that they can’t attack Iran forever.

“Make clear to the Iranians that there’s still a deal on the table. We’re willing to negotiate,” Goldenberg said. “And at the same time, make clear to the Israelis, there are limits to this. We can’t see this get out of control.”