Looking ahead to the final two years of President Obama’s second term, analysts are positing that this Administration will turn its focus away from domestic issues and toward cementing a foreign policy legacy. To that end, the remainder of 2014 and the beginning of 2015 will be decisive. In the coming days and months, the Administration is likely to make major decisions on whether and how to achieve historic diplomatic détentes with two of the country’s long-standing foes, Iran and Cuba.As Administration officials carry on those discussions in the West Wing, five Americans—a Washington Post correspondent, a former Marine, a Christian preacher, an FBI agent, and a USAID contractor—sit in captivity, held by the very governments with which the White House would seek renewed relations. President Obama has an opportunity to leverage negotiations with Iran and Cuba to bring these imprisoned Americans home. But with nuclear negotiations set to expire in a matter of days barring an extension, and with the clock ticking for a critical facet of détente with Cuba, the question is, will he?Regarding Iran, it appears that the Administration will not link the release of Americans to a nuclear deal; it is very possible that a deal would be consummated without ensuring their release. With respect to Cuba, the American prisoner himself may be the key to normalization—if the President acts now.Nearly four months ago, Iranian authorities arrested Jason Rezaian, the Washington Post’s Tehran correspondent, along with his wife, journalist Yeganeh Salehi, and two American freelance photographers. Rezaian joins a list of Americans held in Iran over the past several years, including Amir Hekmati, a former U.S. Marine, who was arrested in Iran in 2012 while visiting family there; Saeed Abedini, an American Christian preacher, who has been in an Iranian prison since 2012 for espousing his evangelical faith; and Robert Levinson, a former FBI agent, who was abducted in Iran in 2007, and whose precise location is not known. Meanwhile, Alan Gross, a USAID contractor imprisoned in Cuba since 2009 for the “crime” of disseminating communication equipment to members of Cuba’s small Jewish community, languishes in a prison in Havana with two other cellmates.The Administration has not connected the status of American prisoners to a thaw in relations with Iran, though some experts, such as Dennis Ross, counselor at the Washington Institute for Near East Policy and President Obama’s former top Iran advisor at the National Security Council, advocate a more assertive approach to securing their release. According to Ross, “these cases should be raised” during the ongoing nuclear negotiations in Vienna.However, National Security Council Spokeswoman Bernadette Meehan has made clear that the United States does not intend to broach the topic of imprisoned Americans in the context of the P5+1 nuclear negotiations. “We have been very clear publicly since the beginning of the nuclear talks that the P5+1 negotiations with Iran are solely focused on the nuclear issue,” Meehan wrote in an e-mailed statement prior to Rezaian’s arrest. “While the U.S. delegation raises the cases of [American prisoners] with the Iranians in our bilateral meetings on the margins of those talks, the status of the Americans is not a part of the nuclear negotiations.”Ross argues that Rezaian’s imprisonment, as well as that of his wife and photographers, could actually be leveraged to augment America’s position at the negotiating table. “I would not only raise [these arrests] but make it clear that these cases, collectively, now will make reaching an agreement and explaining it more difficult.”Yet the Administration appears to have decided otherwise. Even after Rezaian’s imprisonment, Meehan says that the administration’s policy of not linking their status to progress in P5+1 negotiations holds despite Rezaian’s imprisonment. Thus, it is possible that America will reach a nuclear accord with Iran while still allowing Tehran to hold four Americans, including two former public servants, in captivity.The Administration has pursued a different policy altogether with respect to Alan Gross and Cuba. Unlike the nuclear negotiations with Iran, it has made clear publicly that any thawing of ties between the United States and Cuba is contingent on a negotiated deal that results in Alan Gross’ freedom. According to a February 2014 Atlantic Council poll, a majority of both Democrats and Republicans, as well as a significant majority in Florida (home to the country’s largest Cuban-American population), currently favor this shift in policy. “I cannot emphasize enough that Cuba’s continued detention of Alan Gross is a major impediment to improved relations between the United States and Cuba,” Vice President Joe Biden told a Cuban media outlet earlier this year.For its part, the Castro regime in Cuba has made clear that, in order for Gross to be released, the United States must free the three remaining members of the of the so-called “Cuban Five,” a group of Cuban intelligence officers convicted in 2001 of crimes related to espionage and conspiracy against the U.S. government.To win Gross’s freedom, the Obama Administration will have to act quickly. Gross, 65, has said that 2014 will be the last full year that he remains in Havana; rather than turn 66 in confinement, he is determined to make it out “dead or alive.” According to Gross’s lawyer, Scott Gilbert, Gross is “deadly serious”:
Look, it is very simple. Alan has been confined to one small room with two other prisoners for five years. He cannot see out of his right eye, his hips are so bad that he has not gotten any exercise in months, and he has lost most of his body mass. Physically, he is just getting worse. Alan turned 65 in prison in May and then sat helplessly in his cell while his mother died without her son. His family has endured countless hardships without their husband, father and brother. He has told me that he simply won’t spend another year in prison as his life goes on without him.
Through the Cuban government’s persistent messaging and public rallying, the case of the “Cuban Five” has become a cause célèbre in the Cuban street. Between Cuba’s public demand for a trade and America’s requirement that Gross be freed before bilateral ties warm, neither side has offered any face-saving alternatives to a negotiated deal. Thus, if Gross dies before such a deal is consummated, any chance that the Obama Administration has for rapprochement with Cuba could perish with him.America’s relationship with two longtime enemies may be about to undergo fundamental change, and with it, America stands to potentially recover five of its own. Should the Administration achieve détentes with Iran and Cuba, the headlines of tomorrow will declare that President Obama has cemented his foreign policy legacy.But that will only be partly true, as there is a second part of this legacy at stake. For a Washington Post reporter, a former Marine, a Christian pastor, an FBI agent in Iran, and anyone else considering serving this country in dangerous parts of the world, this is the legacy that matters. And for a USAID contractor imprisoned in Havana, part of that legacy will live—or die —with him.