WASHINGTON – Iran and America are poised for war. The Trump administration has surrounded the Middle Eastern country with a staggering quantity of military personnel and equipment, and many officials and experts now see an American strike within weeks as inevitable, likely to spur a sharp Iranian response, then a spiraling and gruesome conflict. The best way to avert that outcome is successful diplomacy, but its prospects are extremely slim. Trapped in Iran’s most notorious jail is an ailing Iranian American journalist whose situation helps explain why: Reza Valizadeh.

Imprisoned by Iranian authorities over his ties to the U.S. and work as a reporter, Valizadeh was deemed “wrongfully detained” by the State Department in May 2025. That unlocked “special consideration” and government resources to help free him, a GOP congressional aide told HuffPost. The status bolstered Valizadeh’s relevance to President Donald Trump’s personal “commitment to leaving no American behind” and to Washington’s overall claim of fighting Iranian repression.

“We have a lot of faith in the negotiators [with Iran] and the president. This has been a top-of-mind issue for him and for the administration: They don’t waver on bringing people home,” the Republican aide said, saying Trump had so far freed roughly 150 Americans held abroad. Asked for comment on Valizadeh, the State Department sent HuffPost a statement from a U.S. official demanding his release and that of “all others unjustly detained in Iran,” adding: “The Iranian regime has a long and shameful history of unjustly detaining U.S. nationals.”

But today, the likeliest scenarios for Valizadeh’s release appear extremely improbable. That is in part because of the Trump administration’s choices as it has both negotiated with Tehran and subjected it to military and economic pressure — including direct American attacks last summer — in pursuit of limits on Iran’s nuclear program, missile capabilities and regional influence. Meanwhile, Iran’s own calculations complicate the prospect too.

Previously, agreements between U.S. and Iranian officials to exchange prisoners like Valizadeh have helped Washington and Tehran reduce tensions.

Ryan Fayhee, Valizadeh’s attorney in the U.S., said he does not believe the two countries are now considering such a swap. Instead, Fayhee sees Iran releasing Valizadeh and other U.S. citizens “to reset their own standing in the region and to allow for a greater focus on the issue or issues the Iranians want to engage the U.S. on.”

Iran’s other American detainees include two septuagenarians, he said, arguing such detentions hurt the country’s international image. (At least four Iranian-Americans are estimated to be in Iranian captivity.) And Fayhee noted Tehran does not appear to be pushing Washington to release any of its citizens held in the United States.

“I don’t know exactly what the U.S. government strategy is [but given] initial contacts, I’m feeling very optimistic that there’ll be an opportunity to discuss these matters, because previously there were not communications,” Fayhee told HuffPost.

A gesture of goodwill or PR bid by Iran is conceivable, but hard to imagine amid constant threats and conflicting messages from Trump. The president on Friday said he is considering a limited attack on Iran, the day after he said he still believes a deal is possible. Trump framed an assault as a negotiating tactic. Yet even an ostensibly modest strike would cause Iran to “walk away” from talks with Trump, a senior diplomat from the region told HuffPost on Thursday.

Iranian leaders, who are attempting to reassert power after brutally suppressing domestic protests last month, are reluctant to appear weak relative to the U.S. or make big concessions, but the Trump administration continues to demand sweeping restrictions on Iran that would be perceived as a capitulation. Talks between envoys in Switzerland on Tuesday offered little evidence of a compromise. On Thursday, the U.S. official told HuffPost: “Progress was made, but there are still a lot of details to discuss. The Iranians said they would come back in the next two weeks with detailed proposals to address some of the open gaps in our positions.”

Some analysts believe that given those gaps and the signs Trump is leaning toward an attack, Iran’s leadership now sees outright fighting as its best step strategically, rather than taking steps to de-escalate by, for instance, freeing American detainees.

“Tehran may calculate that the longer the war lasts and the higher the stakes become, the U.S. will be more likely to look for a way to end it. Negotiations then could yield a different — and more desirable — result for Iran,” Vali Nasr, a Johns Hopkins University professor, wrote in the Financial Times on Thursday. “Many in the west will interpret this line of thinking as a catastrophic miscalculation… But it would be a mistake if they dismiss it.”

Iran’s assessments of its options draw partly on its interpretation of U.S. moves. As Trump’s negotiating team — dominated by special envoy and fellow real estate developer Steve Witkoff and now including the president’s son-in-law, Jared Kushner — has held discussions with Iranian counterparts, few indications have emerged that those talks prioritize American detainees.

“Shockingly, the administration has completely dropped the case of American hostages in Iran. They haven’t brought it up even once,” said Ali Vaez, an analyst at the International Crisis Group think tank. “I hope that this will be part and parcel of a deal, not as a follow-on to it.”

When HuffPost asked the regional official if Iran might free jailed Americans to improve the tone around the talks, the official said it would be best for the dialogue to focus narrowly on Iran’s nuclear program, in the vein of the last agreement between Iran, the U.S. and other world powers (which Trump weakened and then abandoned despite Iranian compliance).

In Iran’s view, the U.S. is already in violation of a prior agreement over detainees, Vaez noted. In September 2023, the Biden administration agreed to let Iran tap $6 billion in frozen oil revenue held outside the country as part of a prisoner exchange deal, only for Washington to freeze the money again after the Oct. 7, 2023, attacks on Israel by the Iranian-backed Palestinian militia Hamas, which led to the massacre of hundreds of civilians.

Iranian officials raised that money in talks with the Trump administration last year, a former U.S. official told HuffPost, arguing their concern was not even the amount but evidence that the U.S. would follow through on its word. Trump made “an explicit decision not to release the funds,” the official said.

Iran does not appear to “recognize the political toxicity that exists for this administration” regarding the Biden-era agreement, the former official continued, noting the freeze was widely treated in Washington, including by many Democrats, as “the de facto punishment for Oct. 7.” Any attempt to free the money would likely draw sharp resistance from Congress and fresh gambits to target Iran.

With the two sides “talking past each other,” the latest U.S.-Iran discussions “went poorly,” the former official said. Asked about the administration’s avowals that it would like to avoid a war, the official recalled Trump’s negotiations with Tehran before the Israeli offensive against the country last year that the U.S. joined: “I thought we were against the June war until we weren’t.”

Held in a cell in Evin prison along with 17 others, in a ward where 200 inmates share four toilets and without access to essential prescription throat medication or treatment for his dental and gastrointestinal issues, Valizadeh is among those who would be most vulnerable if a U.S.-Iran conflict breaks out. HuffPost drew information about his case and conditions from a report Fayhee prepared for United Nations experts.

Now 50, the jailed reporter was arrested in September 2024, after he traveled to Iran to visit his elderly parents upon receiving assurances he would not be targeted for his years of criticizing the Iranian government and working for Radio Farda, a Persian news outlet funded by the U.S. government. He was held in solitary confinement and interrogated, including about his radio work, for more than two months, before being sentenced following brief hearings in an Iranian court where the judge also acted as the prosecutor. Valizadeh’s attorney was not allowed to represent him, the report says, and his appeal was rejected in January 2025.

War has worsened Valizadeh’s 18-month imprisonment. During the U.S.-Israeli bombing of Iran last summer, the Israeli military hit the Evin prison in an apparent war crime, killing and injuring civilians. Valizadeh was near one explosion. He and other screaming prisoners faced another blast, then were shot at by guards and “hovered between life and death,” Valizadeh’s brother told the Committee to Protect Journalists last year.

The smoke severely worsened Valizadeh’s asthma and led to his being briefly transferred to another prison known for contaminated food and greater isolation, according to his brother.

Detained Americans’ conditions could be a factor as Trump weighs a strike and a possible tit-for-tat conflict with Iran, endangering tens of thousands of other Americans across the Middle East.

“That’s a significant variable in this in that the protection of American citizens is one of the government’s most sacred priorities,” the GOP aide said. “It’s a consideration moving forward, in particular regarding Evin prison. That’s front of mind not only for [Valizadeh’s] advocates but also the administration.”

But the Trump administration has also subjected hundreds of U.S. citizens to violence and detentions and suggested some should be stripped of citizenship. And in dealing with people linked to Iran, it has claimed to support their human rights, including to dissent against the Iranian government, while barring most Iranian nationals from traveling to America and causing mass impoverishment through sanctions.

The U.S. official who emailed HuffPost wrote: “We remind U.S. nationals of the warning on travel.state.gov: ‘Do not travel to Iran for any reason.’ Americans there should leave.”

For Valizadeh, that is not an option.