The Islamic Republic might believe it has the upper hand as negotiations restart in Italy between its foreign minister, Abbas Araghchi, and President Trump’s special envoy, Steven Witkoff. Will the Saturday talks, then, turn into an Iranian version of Hollywood’s 1953 “Roman Holiday”?

“Traditionally, Italy has been Europe’s weak link on Iran” a Tehran watcher at Israel’s Institute for National Security Studies, Beni Sabti, tells the Sun. “Since the 1990s there have been extensive trade ties” between the countries. “Revolutionary Guards types went to study in Italy. The works.” Under Prime Minister Meloni, he adds, relations might be less favorable for Iran.  

Ms. Meloni is scheduled to visit the White House later this week, and before negotiations resume in her country, as Mr. Trump toughens up his talk on Iran. “These are radicalized people and they can have a nuclear weapon,” he said Monday. “If we have to do something very harsh, we’ll do it. And I’m not doing it for us, I’m doing it for the world.” Asked if that includes military strikes on nuclear facilities, he said, “of course it does.”  

Tehran might hope to use Italy against the three European members of the 2015 Iran deal, known as the Joint Comprehensive Plan of Action. Britain, France, and Germany increasingly signal they would use a United Nations motion known as snapback to reimpose the onerous global sanctions on Iran that existed before the deal rescinded them. 

“A source tells me the Islamic Republic of Iran has been pushing for Italy’s involvement in negotiations for some time now to diminish the E3’s (UK, Germany & France) active role in talks,” a United Against Nuclear Iran researcher, Kasra Aarabi, writes on X. “Another tells me Tehran has calculated E3 will activate snapback by June/July.”

Iranians might believe Rome is a good venue for them. Further, they say that Mr. Trump’s decision to charge his long-time friend, Mr. Witkoff, with handling the talks is to their advantage 

“Trump wanted his State Secretary Marco Rubio to take part in Iran talks, but we insisted on Witkoff, and the U.S. backed down,” the deputy head of the Iranian Parliament’s Foreign Policy Committee, Mahmoud Nabavian, is quoted by Iran International as saying. “In every aspect of the negotiations, whatever we said was accepted, and the American side gave ground.” 

Yet, Tehran gave ground by merely returning to the negotiations table after the supreme leader long opposed “useless” diplomacy with Mr. Trump.  “The Iranians are spinning and seeking to amplify perceived fissures in the U.S. administration,” United Against Nuclear Iran’s policy director, Jason Brodsky, tells the Sun.

Washington’s public statements, though, do point to some fissures. National security adviser Mike Waltz, Mr. Rubio, and Secretary Hegseth repeatedly say that the goal of diplomacy is “full dismantlement” of Iran’s nuclear infrastructure. Mr. Witkoff has countered that compromises can be discussed as long as a red line — “weaponization” — isn’t crossed. 

Mr. Witkoff is also negotiating over Gaza hostages. Last week he flew to Russia to negotiate an end to the Ukraine war, where “he hasn’t produced much of anything,” the founder of the Institute for Science and International Security, David Albright, tells the Sun. “And now he’s joined a very complicated nuclear deal with Iranians who are very adept at negotiations. He’s just way over his depth.”

Dismantling the Iranian nuclear infrastructure will be more difficult than the successful end to Libya’s program. In 2003 Muammar Qaddafi, in the aftermath of Saddam Hussein’s ouster, announced his readiness to end Libya’s nuclear ambitions and have the International Atomic Energy Agency verify it.

Mr. Albright, who participated in the IAEA verification in Libya, says a similar process with Iran would be much more difficult. In Libya, “a significant program was dismantled, but it was not nearly as large as Iran’s,” he says. 

Additionally, he says, unless the Iranians believe that the process is in their interest, it will be impossible to “really dismantle the program for the long term. As soon as you turn your back, they can start springing back into action.”

To assure that the Iranian program is indeed fully and verifiably dismantled the Islamic Republic must genuinely want it gone. “Iran needs to feel that the regime is going to collapse,” Mr. Albright says.  “I’m not sure these negotiations are going to get anywhere close” to that. 

Mr. Trump vows to prevent the talks from dragging on. After Mr. Witkoff returned Saturday from Oman, the president said he will make a decision “very quickly.” Two American aircraft carriers are in the region, alongside B-2 bomber jets. Israel, too, is reportedly in the final planning stages for strikes on Iran’s nuclear facilities.