02 US detainees 091023
CNN  — 

In the final hours as the United States closed in on a controversial but historic deal to bring five Americans deemed wrongfully detained in Iran home, Iranian officials threw up roadblocks, attempted to force the US government to make last minute concessions and even stalled the process minutes before the detainees were set to board a flight out of Tehran.

CNN has learned new, behind-the-scenes details about the final few days and the obstacles American diplomats had to navigate as they sought to ensure a diplomatic breakthrough that had been years in the making did not fall apart in the crucial last stages. Senior State Department officials spoke to CNN about what happened on the condition of anonymity to discuss the sensitive details.

According to the officials, acting US Special Envoy for Iran Abram Paley and Special Presidential Envoy for Hostage Affairs Roger Carstens arrived in Doha on Saturday afternoon to coordinate with Qatari and Swiss officials on the logistics for the release of the five American detainees and two of their family members, which they anticipated would take place on Monday.

The diplomatic relationship with Iran is incredibly tense and even though years of painstaking indirect negotiations had brought the process to an apparent finish line, the Americans had to contend with last minute efforts to stall and try to get more out of the US, despite the two sides having an agreed-upon deal.

The Iranians even threatened not to include all five of the Americans in the release unless the US did more, the officials told CNN.

But having come this far, the Americans made clear they were not going home without all five – it was a non-negotiable to the US and the Iranians relented.

“We held our line and the Iranians backed down and we made it work,” a senior State Department official said.

The US officials suggested the negotiators didn’t see these Iranian attempts as a significant threat that could sink the deal, but rather as part of a typical strategy by Tehran.

“They’re always just trying to throw sand in the gears, always trying to negotiate and try to get more and more,” the official said. “We’ve taken a very firm line and a very principled position, so we stood firm.”

Still, “each hour there was something new that the Iranians were trying to stall with or just be difficult for the sake of being difficult,” they added.

Hurdles on the day of departure

The Americans felt confident that the deal itself was enticing enough that Iran wouldn’t actually walk away and that it was strong enough that they couldn’t renege on it and still get what they wanted. Under the agreement, $6 billion in Iranian funds were transferred from restricted accounts in South Korea to restricted accounts in Qatar to be used for humanitarian purchases, and the US would release five Iranians from US custody.

The last of the Iranian funds reached the bank accounts in Qatar on Monday, and the US had coordinated with the Qatari officials to notify Iran that the funds had arrived, which would then set off a sequence of steps to lead to the release.

There was a delay, however, because the Iranian officials “couldn’t find the head of the Central Bank to sign some letter that they had to transmit throughout their interagency to then authorize people to let them leave the hotel and go to the airport to pave the way for everything,” the senior State Department official told CNN.

But the money arrived, and everything seemed set. But nothing in this process was simple and even in the hours before the freed Americans were set to board a Qatari jet from Iran to Doha, Iranian officials were still trying to cause delays, the officials told CNN.

The Iranians tried to insist that everyone, the released prisoners and diplomats from all sides, have lunch at the airport in Tehran before departing. But the Qatari officials, in a smooth diplomatic maneuver, countered that they would be offended if everyone did not eat while on board the Qatari plane and an agonizing final delay was avoided.

Having navigated the series of late hurdles, the Qatari plane carrying Siamak Namazi, Morad Tahbaz, Emad Shargi, and two other freed detainees whose names are not publicly known, as well as Namazi’s mother, Effie, and Tahbaz’s wife, Vida, took off from Tehran shortly before 9 a.m. ET on Monday.

US citizens Siamak Namazi (R), Emad Sharqi (L) and Morad Tahbaz (C) disembark from a Qatari jet upon their arrival at the Doha International Airport in Doha on September 18, 2023.