American officials involved in efforts to negotiate the release of detainees are viewing the Taliban’s recent release of a U.S. citizen in Afghanistan as a positive development. This could signal a breakthrough toward a more comprehensive prisoner exchange agreement involving other Americans held in the country.
However, the path to such a deal remains incredibly challenging. The Taliban is insistent on the release of a high-ranking Al Qaeda operative currently held at the U.S. naval prison in Guantánamo Bay. Furthermore, the precise whereabouts of several other Americans in Afghanistan are still unknown, potentially even to the Taliban themselves, highlighting the intricate nature of these negotiations.
Both parties stand to gain significantly from an agreement. The Taliban seeks global recognition and legitimacy, while President Trump has consistently prioritized securing the freedom of Americans detained abroad throughout his two administrations.
President Trump’s stance on securing such a deal with the Taliban was unequivocal. Following the release of American citizen Amir Amiry, Sebastian Gorka, one of the president’s senior counterterrorism advisors, affirmed on social media that “All Americans must come home. That means all.”
Mr. Gorka, along with Adam Boehler, the Trump administration’s special envoy for hostage response, personally escorted Mr. Amiry on his journey home. Mr. Boehler, who has made multiple visits to Afghanistan this year for negotiations, was pictured wearing a jacket adorned with the flags of both the United States and Qatar, underscoring Qatar’s crucial intermediary role in these discussions.
A State Department spokesperson confirmed on Tuesday that “Amir Amiry’s release was a positive step by the Taliban as we work towards the release of all Americans detained in Afghanistan.”
The Taliban has not yet responded to inquiries for comment. Afghanistan has experienced a widespread internet blackout since Monday, effectively halting communications. This disruption follows an order from the country’s leader, Sheikh Haibatullah Akhundzada, aimed at curbing the spread of “vice,” as confirmed by a diplomatic official who spoke anonymously about the restrictions. Both this official and an Afghan Foreign Ministry representative indicated that the blackout would persist indefinitely.
A significant obstacle to a comprehensive deal is the Taliban’s ability to account for every American held in Afghanistan. This includes Paul Edwin Overby Jr., a Massachusetts author last seen in 2014 in Khost, a city in the southeastern region of the country, where he was conducting research for a book. U.S. investigators harbor concerns that he may be deceased, and if so, it remains uncertain whether the Taliban possesses knowledge of his remains.
According to congressional documents and U.S. officials, two other American citizens, Dennis Walter Coyle and Polynesis Jackson, a former U.S. Army soldier, are also being held by the Taliban. While the State Department has officially designated Mr. Coyle as wrongfully detained, the circumstances surrounding Mr. Jackson’s custody are less clear.
Mahmood Shah Habibi is another American who vanished in Afghanistan. The State Department reports he was abducted in August 2022. He and his colleagues at a telecommunications firm were detained by Afghan authorities after the C.I.A. eliminated Ayman al-Zawahri, the leader of Al Qaeda, in Kabul that same month.
In June, the State Department offered a reward of up to $5 million for any information leading to Mr. Habibi. However, officials noted that the Taliban had provided no details regarding his whereabouts or condition.
Ahmad Habibi, Mahmood Shah Habibi’s brother, commended the Trump administration’s efforts to secure his sibling’s freedom. He stated, “My brother is an innocent American and he deserves to come home.”
Eric Lebson, an advisor to the Habibi family and a former U.S. national security official, emphasized that any agreement excluding Mr. Habibi or his remains would be unacceptable to the family and, in his view, “should also be to President Trump.”
On their part, Taliban officials have specifically focused on the repatriation of Muhammad Rahim. He is a man suspected of being an Al Qaeda operative, captured in Lahore, Pakistan, in June 2007, and subsequently held for many months by the C.I.A., according to a U.S. official and other sources familiar with the negotiations.
The U.S. government has accused him of serving as a “translator, courier, facilitator and operative for the group’s senior leadership, including Osama bin Laden.”
The United States further alleges that Mr. Rahim possessed prior knowledge of the September 11 attacks and has consistently “sought to intimidate and taunt his captors even if it means never being released and dying as a martyr, which he appears to welcome.”
In March 2008, Mr. Rahim became the final detainee transferred by the George W. Bush administration to the Guantánamo Bay prison as a combatant in the war against terrorism. Notably, he has never faced formal charges or appeared before a court.
A U.S. interagency intelligence review board has repeatedly advised against his release, with the most recent recommendation in July 2024. They have consistently cited his detention as a national security imperative. The C.I.A. remains opposed to his release.
Carol Rosenberg contributed reporting, and Kitty Bennett contributed research.