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Can Trump secure release of all US hostages in Iran?

Another prisoner exchange between Iran and the United States seems possible after two in just six months, but the previous exchanges have not generated any mutual trust.
Michael White, a freed U.S. Navy veteran detained in Iran since 2018, poses with U.S. Special Envoy for Iran Brian Hook while on his return to the United States at Zurich Airport in Zurich, Switzerland June 4, 2020.  U.S. State Department/Handout via REUTERS. THIS IMAGE HAS BEEN SUPPLIED BY A THIRD PARTY. THIS IMAGE WAS PROCESSED BY REUTERS TO ENHANCE QUALITY, AN UNPROCESSED VERSION HAS BEEN PROVIDED SEPARATELY. - RC2K2H90N3HH

On the surface, momentum seems to be building toward a further prisoner exchange between Iran and the United States. After two detainee swaps in the past six months, both sides have expressed a desire for more. The Donald Trump administration has made winning the release of US citizens a priority, and the Hassan Rouhani administration called for its own citizens to be allowed to come home. Yet the previous exchanges have not generated any mutual trust.

On June 5, Iran turned over Navy veteran Michael White to US special representative for Iran Brian Hook in Zurich. White had been held in Iran for nearly two years on charges of "insulting the country's top leader” and publicly “posting a private photograph.” The United States then reciprocated by releasing Majid Taheri, an Iranian-American doctor who had been held over a sanctions violation. Science professor Sirous Asgari, who had also been caught up on a sanctions charge, was also allowed to return to Iran, although the United States said his case was unrelated to White’s. These releases followed a similar exchange in December, when Iran freed Princeton graduate student Xiyue Wang, a US citizen who had been held for three years on spying charges, and American authorities freed stem cell scientist Massoud Soleimani, who faced sanctions charges.

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