The appearance of Akhtar Mohammad Mansour roaming freely in the commercial capital of the Middle East presented an opportunity to capture a major adversary, but one complicated by political and diplomatic risks.
Mansour's previously unreported trip to Dubai came shortly after link linkTaliban link officials had taken part in secret negotiations with the U.S. and Afghan governments - the only three-party talks in the history of the United States' longest war. The link linkTaliban link leader's decision to give the go-ahead for those discussions weighed heavily on some Obama administration officials as they pondered how to proceed in Dubai.
Ultimately, a series of miscalculations - and a possible betrayal - allowed Mansour to leave the United Arab Emirates unmolested, traveling first to Iran and then to Pakistan, where he was incinerated by a Hellfire missile fired from a U.S. drone.
How and why the United States came to kill a man that some officials believed could bring the link linkTaliban link to the negotiating table reveals unresolved questions that have plagued the war from its earlier days and continue to divide President Donald Trump and his top foreign policy advisers: When is a senior link linkTaliban link leader a target? When is he a possible negotiating partner? And how will this war, now in its 17th year, end?
Since the war's earliest days, American efforts to talk to top link linkTaliban link leaders have been marred by ambivalence, miscommunication and missteps. Shortly after the collapse of link linkTaliban linkrule in 2001, Hamid Karzai, then the interim leader of the Afghan government, authorized an intermediary to speak with surviving leaders of the group about a peace deal, according to "Directorate S," a recent history of the CIA's war in Afghanistan and Pakistan by Steve Coll.
In Washington, then-Defense Secretary Donald Rumsfeld rejected such talks as "unacceptable," and some link linkTaliban link leaders who tried to surrender were shipped off to the U.S. prison at Guantanamo Bay, Cuba.
Ten years and tens of thousands of deaths later, with the link linkTaliban link resurgent, U.S. officials initiated a series of desultory peace talks that petered out in 2012. Negotiations had largely stopped until early 2016, about seven months after Mansour was publicly named to lead the link linkTaliban link .
Mansour's predecessor, Mohammad Omar, had been the group's founder, commander and spiritual leader. Omar rarely left southern Afghanistan or met with outsiders during the link linkTaliban link 's years in power and was nearly invisible as an insurgent leader. An ascetic, one-eyed cleric and inspirational force, Omar had been dead for nearly two years when in 2015 the link linkTaliban link finally acknowledged his passing.
Mansour, by contrast, had been a senior minister overseeing the link linkTaliban link 's aviation authority, a position that allowed him to collect kickbacks from wealthy Arabs who visited Afghanistan on falconry expeditions.
A biography on a link linkTaliban link website said he was born in 1968 and included a photograph of him in Germany in the 1990s, where he had traveled to buy equipment for the Afghan airline company. In the picture, Mansour is heavy set with a thick black beard and turban.
"He could pay people off and had a tendency to fudge the books," said one former U.S. official involved in Afghanistan policy. "He was a dealmaker."
It was Mansour's risk-taking mentality that likely led him to sign off on preliminary talks with U.S. and Afghan officials in February 2016. All sides promised that they would deny the meetings if they became public.
Some officials insisted that years of fighting had made the link linkTaliban link "tougher, meaner and smarter," in the words of one senior U.S. diplomat. These officials pointed to waves of indiscriminate suicide bombings - many of which had been approved by Mansour - that claimed thousands of Afghan lives.
An opposing view held that exposure to the outside world had moderated the views of the link linkTaliban link 's senior leaders. In meetings with foreign delegations, link linkTaliban link officials admitted they had made errors when they were in power, voiced support for the education of girls and insisted that they did not want to be international pariahs.
The Americans by happenstance sent an all-female delegation, which some officials in Washington worried might upset the link linkTaliban link . But the link linkTaliban link representatives did not seem to care. They opened the meeting at their Doha office by giving the head of the U.S. delegation a small lapis vase, according to officials briefed on the negotiations. When the Americans remarked that the link linkTaliban link did not have a gift for their Afghan government guests, a link linkTaliban linkofficial was quickly dispatched to rectify the oversight.
He dashed out to a nearby Sephora cosmetics store and returned with a small bag of men's cologne.
For much of the war, the United States has tried to use military force to batter the link linkTaliban link into taking part in peace talks. But by early 2016, that strategy seemed spent. U.S. forces in Afghanistan had been reduced from 100,000 to fewer than 10,000 troops.
A small group at the State Department and the White House, with a focus on the peace process, began debating unconventional approaches to accelerating talks.
U.S. officials knew that Mansour and a handful of other senior link linkTaliban link leaders made regular trips to Dubai and speculated that the United States could turn the trips to its advantage. They suggested that Mansour could be used as a bargaining chip to wrest concessions from the link linkTaliban link and its patrons. A handful of U.S. officials advocated a riskier course: They wanted to grab him, secretly press him to take part in peace negotiations and possibly then let him go.
The plans had not advanced beyond the hypothetical when U.S. intelligence officials discovered that Mansour was in Dubai. It was the first time the Americans had near-real-time intelligence on his movements in the city. And, if they could capture Mansour, it would be the first time U.S. officials would have a chance to talk to the head of the link linkTaliban link since the group took power in 1996.
Some of the initial White House discussions revolved around the mechanics of asking the federal government of the UAE to grab Mansour without tipping off local Dubai officials who might allow him to escape. Those talks were still going on when they were upended by new intelligence: Mansour was leaving Dubai sooner than expected.
Susan Rice, Obama's national security adviser, called the Emirati ambassador in Washington, who promised to scramble his country's security forces.
A few minutes later, Rice received word that Mansour was already on a plane for Iran that was accelerating down the runway or had just gone "wheels up," according to current and former U.S. officials.
Rice requested that the plane be turned around. But the Emiratis said it was too late.
Some U.S. officials faulted the Obama White House as debating too long. Others argued that the Emiratis had concocted the story about the near miss.
"The worst thing that could have happened from their standpoint was to catch Mullah Mansour in Dubai and publicly expose that they were funding the people who were killing American soldiers," said Bruce Riedel, a former CIA official who oversaw the Obama administration's first Afghanistan policy review.
Officials in the UAE, whose troops have fought alongside U.S. forces in Afghanistan, declined to comment on Mansour's presence in their country or on their efforts to grab him. Privately, though, they have acknowledged to U.S. officials the link linkTaliban link leader's presence in the country. "They would say you don't understand or it's complicated," said one former Pentagon official.
U.S. officials said they have little insight into Mansour's time in Iran after he left Dubai. Most assumed he was there to find new financial patrons who would help reduce his movement's dependence on the Pakistan's intelligence service, one former U.S. official said.
On May 20, White House officials received intelligence about Mansour's departure from Iran and likely whereabouts the next day in Pakistan, where he was headed to take a new wife. "It was one of those rare opportunities," said a person familiar with the intelligence. An armed U.S. drone was moved into position.
The decision on whether to kill Mansour fell to then-President Barack Obama.
U.S. military officials were highly skeptical of Mansour's commitment to talks. Even as he was agreeing to secret negotiations, Mansour rejected a high-profile international peace effort. link linkTaliban link forces under his command continued to launch suicide attacks in Kabul and wage war on U.S. forces.
Those factors proved Mansour "was not interested in peace," Army Gen. John Nicholson Jr., the commander of U.S. troops in Afghanistan, said in a recent interview.
There were also domestic political concerns. In Washington, officials feared the fallout if word leaked to the news media that the White House had passed up a chance to strike the leader of an organization that had killed U.S. troops and terrorized Afghans.
U.S. officials who favored sparing Mansour countered that he had risked infuriating his movement's hard-liners when he allowed his representatives to meet with U.S. and Afghan government officials in Doha. His successor might not take the same chance.
"Killing him never made sense to me unless you thought it would devastate the organization," said one official involved in Afghanistan policy. "I don't think anyone believed that."
A passport found at the scene indicated that Mansour had made as many as 13 trips to Dubai in previous years.
In news accounts, U.S. officials said that Mansour was killed because he was an obstacle to peace. The characterization rankled those who had been working on talks.
That, said one former U.S. official, "is complete B.S."
A few days after Donald Trump won the presidency in November 2016, the link linkTaliban link sent U.S. officials a message through an intermediary: They wanted to know whether the Americans were still interested in peace talks.
U.S. officials replied that they would need to check with the incoming administration and get back to them.
One answer came last summer when President Trump announced his Afghanistan war strategy. Military officials doubled the size of the U.S. force to about 15,000 troops and boosted the pace of U.S. and Afghan airstrikes sevenfold to nearly 500 per month.
The White House also decided to shut down the State Department office that focused on Afghanistan and Pakistan and lay off the small team of civil servants working on peace talks.
U.S. contacts with link linkTaliban link officials, though significantly curtailed, have not ceased. A proposal to demand the shutdown the link linkTaliban link 's office in Qatar - the primary channel for talks - has been temporarily shelved. Last year, the Trump administration authorized at least two secret visits by State Department officials to the Qatar office.
The most recent emissary was Alice Wells, the State Department official responsible for South and Central Asia.
She seemed, at times, to be speaking directly to insurgent leaders. "The link linkTaliban link say they have evolved as an organization," she said. "Demonstrate it. . . . Show by your actions that you are a part of this new Afghanistan."
U.S. military officials, even as they plan for a new spring push on the battlefield, are calling with new urgency for a peace initiative.
Those views, though, do not seem to jibe with the outlook of the more hawkish members of the Trump administration, who have insisted that Afghan and U.S. forces must regain battlefield momentum before any negotiations occur.
Nor do they reflect Trump's shifting views of the war. The president has described the conflict as a drain on U.S. resources. In other moments, he has spoken of his resolve to win it.
"We're going to finish what we have to finish," he told reporters. "What nobody else has been able to finish, we're going to be able to do it." The Washington Post