President Donald Trump’s decision to negotiate directly with Hamas for a cease-fire and hostage-release deal, to keep Israel in the dark about elements of the secret back-channel conversations, and then write a letter to Iranian Supreme Leader Ayatollah Ali Khamenei expressing interest in negotiating a nuclear deal are being viewed warily by some pro-Israel leaders as a break from the president’s first-term toughness against the Islamic Republic.

But the unconventional moves, particularly the push for a nuclear deal, are being received favorably by an unlikely group — progressive foreign policy officials from the Obama and Biden administrations.

The administration’s moves, which have drawn objections in private from the Israeli government and public concerns from pro-Israel conservatives, are reminiscent of former President Barack Obama’s efforts to reach a nuclear deal with the Islamic Republic, foregoing tougher sanctions and military pressure.

Like Trump, Obama wrote a letter to Khamenei, trying to nudge Iran’s leader toward a nuclear deal. Obama regularly faced criticism over his back-channel diplomacy with America’s enemies that sometimes left Israel out of the loop.

Khamenei has publicly rejected Trump’s diplomatic overtures.

Democratic boosters of the original Iran deal are backing Trump’s letter, and sound more enthusiastic about his efforts toward a nuclear deal than those most supportive of the president’s hawkish first-term Iran policy.

Philip Gordon, the national security advisor to former Vice President Kamala Harris, said that Trump’s interest in a deal was a “welcome” development.

“Obviously, it’s ironic that Trump would be the one who would be pushing for a nuclear deal with Iran having denounced the previous one,” Gordon, who also served in the Obama administration, told JI. “But remember, he denounced it because he said it wasn’t a good deal … One reason he might be able to do it, want to do it, is he could arguably get a ‘better’ deal than Obama.”

And, Gordon continued, Trump would likely be able to get the Republican Party in Congress to back a deal he negotiated, something that GOP legislators would likely not have done for a Biden-negotiated deal.

“If we could get a deal with even better terms than the last one and deal with the problem of Iranian nuclear efforts, which has been such a thorn, more power to them,” Gordon said. “I’m not going to be against it just because it’s Trump.”

Ilan Goldenberg, who served as an advisor to the National Security Council and to the former vice president on the Middle East in the previous administration, also praised Trump’s diplomatic moves.

“I have very deep, fundamental disagreements with Donald Trump and a lot of what he’s doing, but when he does the right thing on something, we should support that,” Goldenberg said. “If he wants to have a serious process with Iran where he uses all the leverage that’s been built up against them, I would support that. And I think a lot of Democrats would.”

Goldenberg added that he wasn’t surprised to see the letter, given Trump’s public comments on wanting a new deal and noted, unprompted, that similar outreach happened during the Obama and Biden administrations.

“I think [Trump’s] doing whatever he wants. In some ways he’s supporting the Israelis and in others he’s thumbing his nose,” Goldenberg said, arguing that Trump’s popularity with Israeli Prime Minister Benjamin Netanyahu’s base in Israel gives him more flexibility in his relationship with Israel than past Democratic presidents have had.

Goldenberg and Gordon both argued that Iran’s degraded posture puts the U.S. in a stronger negotiating position now than it was in 2015, when the original deal was signed. Goldenberg said he’s open to a range of configurations for a deal, including one that is ultimately less far-reaching and shorter than the original nuclear deal in exchange for less sanctions relief, if that is ultimately more feasible.

Republicans who backed Trump’s muscular Iran policy in his first term are, comparatively, more hesitant about his new posture and want to see stricter guardrails on negotiations.

“I have no problem with U.S. presidents writing letters to American enemies, as long as there are clear red lines,” said Mark Dubowitz, the CEO of the Foundation for Defense of Democracies. “The clear red line has to be that Khamenei has to commit to fully dismantle Iran’s nuclear program, and Trump has to make clear that if, if he doesn’t, then the United States and Israel will fully dismantle the program for him.”

“My big fear,” Dubowitz continued, “is that the Iranians are going to try to rope-a-dope Trump in the way they’ve successfully done multiple U.S. presidents,” dragging out negotiations, getting significant concessions and a weak deal and ultimately winning GOP support under Trump’s pressure, before later completing a bomb under a less confrontational future president.

Michael Makovsky, the president and CEO of the Jewish Institute for National Security of America, told JI that it’s “dangerous to U.S. interests to enter talks with Iran at this late stage, and the U.S. could be walking into quicksand,” cautioning that Trump needs to set strict parameters to prevent Iran from exploiting the talks.

At the same time, Dubowitz argued that Trump’s recent moves aren’t necessarily a repeat of the Obama playbook, noting that President Ronald Reagan negotiated with the Soviet Union “to keep the Soviets off balance. I think Trump sees it the same way.”

“The difference between Reagan and Obama was that Reagan was prepared to use all instruments of national power to severely weaken and undermine and ultimately collapse the Soviet Union,” Dubowitz said. “And the question is, is Trump willing to do the same with respect to American enemies?… That’s what Obama was not prepared to do, and [President Joe] Biden was not prepared to do.”

Dubowitz also contrasted the “disagreement over tactics” between Trump and Netanyahu over the Hamas talks with the “breach over strategy… a severe fundamental difference of opinion” between Trump and Ukrainian President Volodymyr Zelensky at their contentious recent Oval Office meeting.

Even some who support the prospect of new talks with Iran say they’re worried they could mirror Trump’s unprecedented first-term outreach to North Korea, which culminated in high-profile talks between Trump and Pyongyang’s Kim Jong-Un, and concessions from Trump that delivered little in return.

“Everybody feels good with a big press conference and in exchange, you give up way too much for nothing,” Goldenberg said, characterizing the North Korea talks. But he also said that scenario is less likely with Iran, however, given the Iranians’ lesser interest in a public display with Trump, and the domestic and Israeli pressure Trump will face to reject a weak deal.

Jewish Insider’s senior national correspondent Gabby Deutch contributed reporting.