WASHINGTON – In the spring of 2016 senior officials at the White Houselearned that the head of the Taliban had turned up in Dubai for a few daysof shopping and fundraising.

The appearance of Akhtar Mohammad Mansour roaming freely in the commercialcapital of the Middle East presented an opportunity to capture a majoradversary, but one complicated by political and diplomatic risks.

Mansour’s previously unreported trip to Dubai came shortly after Talibanofficials had taken part in secret negotiations with the U.S. and Afghangovernments – the only three-party talks in the history of the UnitedStates’ longest war. The Taliban leader’s decision to give the go-ahead forthose discussions weighed heavily on some Obama administration officials asthey pondered how to proceed in Dubai.

Ultimately, a series of miscalculations – and a possible betrayal – allowedMansour to leave the United Arab Emirates unmolested, traveling first toIran and then to Pakistan, where he was incinerated by a Hellfire missilefired from a U.S. drone.

How and why the United States came to kill a man that some officialsbelieved could bring the Taliban to the negotiating table revealsunresolved questions that have plagued the war from its earlier days andcontinue to divide President Donald Trump and his top foreign policyadvisers: When is a senior Taliban leader a target? When is he a possiblenegotiating partner? And how will this war, now in its 17th year, end?

Since the war’s earliest days, American efforts to talk to top Talibanleaders have been marred by ambivalence, miscommunication and missteps.Shortly after the collapse of Taliban rule in 2001, Hamid Karzai, then theinterim leader of the Afghan government, authorized an intermediary tospeak with surviving leaders of the group about a peace deal, according to”Directorate S,” a recent history of the CIA’s war in Afghanistan andPakistan by Steve Coll.

In Washington, then-Defense Secretary Donald Rumsfeld rejected such talksas “unacceptable,” and some Taliban leaders who tried to surrender wereshipped off to the U.S. prison at Guantanamo Bay, Cuba.

Ten years and tens of thousands of deaths later, with the Talibanresurgent, U.S. officials initiated a series of desultory peace talks thatpetered out in 2012. Negotiations had largely stopped until early 2016,about seven months after Mansour was publicly named to lead the Taliban.

Mansour’s predecessor, Mohammad Omar, had been the group’s founder,commander and spiritual leader. Omar rarely left southern Afghanistan ormet with outsiders during the Taliban’s years in power and was nearlyinvisible as an insurgent leader. An ascetic, one-eyed cleric andinspirational force, Omar had been dead for nearly two years when in 2015the Taliban finally acknowledged his passing.

Mansour, by contrast, had been a senior minister overseeing the Taliban’saviation authority, a position that allowed him to collect kickbacks fromwealthy Arabs who visited Afghanistan on falconry expeditions.

A biography on a Taliban website said he was born in 1968 and included aphotograph of him in Germany in the 1990s, where he had traveled to buyequipment for the Afghan airline company. In the picture, Mansour is heavyset with a thick black beard and turban.

“He could pay people off and had a tendency to fudge the books,” said oneformer 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 onpreliminary talks with U.S. and Afghan officials in February 2016. Allsides promised that they would deny the meetings if they became public.

One question that divided U.S. officials as they prepared for the secrettalks was whether the Taliban had changed during its years of exile andinsurgency.

Some officials insisted that years of fighting had made the Taliban”tougher, meaner and smarter,” in the words of one senior U.S. diplomat.These officials pointed to waves of indiscriminate suicide bombings – manyof which had been approved by Mansour – that claimed thousands of Afghanlives.

An opposing view held that exposure to the outside world had moderated theviews of the Taliban’s senior leaders. In meetings with foreigndelegations, Taliban officials admitted they had made errors when they werein power, voiced support for the education of girls and insisted that theydid not want to be international pariahs.

U.S. officials received a glimpse of what some of the Taliban had becomewhen they greeted the Taliban and Afghan teams in Qatar – the site of theFebruary 2016 talks.

The Americans by happenstance sent an all-female delegation, which someofficials in Washington worried might upset the Taliban. But the Talibanrepresentatives did not seem to care. They opened the meeting at their Dohaoffice by giving the head of the U.S. delegation a small lapis vase,according to officials briefed on the negotiations. When the Americansremarked that the Taliban did not have a gift for their Afghan governmentguests, a Taliban official was quickly dispatched to rectify the oversight.

He dashed out to a nearby Sephora cosmetics store and returned with a smallbag of men’s cologne.

For much of the war, the United States has tried to use military force tobatter the Taliban into taking part in peace talks. But by early 2016, thatstrategy seemed spent. U.S. forces in Afghanistan had been reduced from100,000 to fewer than 10,000 troops.

A small group at the State Department and the White House, with a focus onthe peace process, began debating unconventional approaches to acceleratingtalks.

U.S. officials knew that Mansour and a handful of other senior Talibanleaders made regular trips to Dubai and speculated that the United Statescould turn the trips to its advantage. They suggested that Mansour could beused as a bargaining chip to wrest concessions from the Taliban and itspatrons. A handful of U.S. officials advocated a riskier course: Theywanted to grab him, secretly press him to take part in peace negotiationsand possibly then let him go.

The plans had not advanced beyond the hypothetical when U.S. intelligenceofficials discovered that Mansour was in Dubai. It was the first time theAmericans 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 Taliban since thegroup took power in 1996.

Some of the initial White House discussions revolved around the mechanicsof asking the federal government of the UAE to grab Mansour without tippingoff local Dubai officials who might allow him to escape. Those talks werestill going on when they were upended by new intelligence: Mansour wasleaving Dubai sooner than expected.

Susan Rice, Obama’s national security adviser, called the Emiratiambassador in Washington, who promised to scramble his country’s securityforces.

A few minutes later, Rice received word that Mansour was already on a planefor Iran that was accelerating down the runway or had just gone “wheelsup,” according to current and former U.S. officials.

Rice requested that the plane be turned around. But the Emiratis said itwas 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 tocatch Mullah Mansour in Dubai and publicly expose that they were fundingthe people who were killing American soldiers,” said Bruce Riedel, a formerCIA official who oversaw the Obama administration’s first Afghanistanpolicy review.

Officials in the UAE, whose troops have fought alongside U.S. forces inAfghanistan, declined to comment on Mansour’s presence in their country oron their efforts to grab him. Privately, though, they have acknowledged toU.S. officials the Taliban leader’s presence in the country. “They wouldsay you don’t understand or it’s complicated,” said one former Pentagonofficial.

U.S. officials said they have little insight into Mansour’s time in Iranafter he left Dubai. Most assumed he was there to find new financialpatrons who would help reduce his movement’s dependence on the Pakistan’sintelligence service, one former U.S. official said.

On May 20, White House officials received intelligence about Mansour’sdeparture from Iran and likely whereabouts the next day in Pakistan, wherehe 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 movedinto 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 totalks. Even as he was agreeing to secret negotiations, Mansour rejected ahigh-profile international peace effort. Taliban forces under his commandcontinued to launch suicide attacks in Kabul and wage war on U.S. forces.

Those factors proved Mansour “was not interested in peace,” Army Gen. JohnNicholson Jr., the commander of U.S. troops in Afghanistan, said in arecent interview.

There were also domestic political concerns. In Washington, officialsfeared the fallout if word leaked to the news media that the White Househad passed up a chance to strike the leader of an organization that hadkilled U.S. troops and terrorized Afghans.

U.S. officials who favored sparing Mansour countered that he had riskedinfuriating his movement’s hard-liners when he allowed his representativesto meet with U.S. and Afghan government officials in Doha. His successormight not take the same chance.

“Killing him never made sense to me unless you thought it would devastatethe organization,” said one official involved in Afghanistan policy. “Idon’t think anyone believed that.”

Shortly after Mansour crossed into Pakistan, a U.S. military drone fired amissile that blew up his taxi, killing the Taliban leader and the driver.

A passport found at the scene indicated that Mansour had made as many as 13trips to Dubai in previous years.

In news accounts, U.S. officials said that Mansour was killed because hewas an obstacle to peace. The characterization rankled those who had beenworking 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, theTaliban sent U.S. officials a message through an intermediary: They wantedto know whether the Americans were still interested in peace talks.

U.S. officials replied that they would need to check with the incomingadministration and get back to them.

One answer came last summer when President Trump announced his Afghanistanwar strategy. Military officials doubled the size of the U.S. force toabout 15,000 troops and boosted the pace of U.S. and Afghan airstrikessevenfold to nearly 500 per month.

The White House also decided to shut down the State Department office thatfocused on Afghanistan and Pakistan and lay off the small team of civilservants working on peace talks.

U.S. contacts with Taliban officials, though significantly curtailed, havenot ceased. A proposal to demand the shutdown the Taliban’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 StateDepartment officials to the Qatar office.

The most recent emissary was Alice Wells, the State Department officialresponsible for South and Central Asia.

This month at a speech in Washington, she said the U.S. objective inAfghanistan was to “bring the Taliban to the negotiating table.”

She seemed, at times, to be speaking directly to insurgent leaders. “TheTaliban say they have evolved as an organization,” she said. “Demonstrateit. . . . 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 thebattlefield, are calling with new urgency for a peace initiative.

Those views, though, do not seem to jibe with the outlook of the morehawkish members of the Trump administration, who have insisted that Afghanand U.S. forces must regain battlefield momentum before any negotiationsoccur.

Nor do they reflect Trump’s shifting views of the war. The president hasdescribed the conflict as a drain on U.S. resources. In other moments, hehas spoken of his resolve to win it.

In January, after the Taliban exploded a bomb in Kabul, killing 103Afghans, Trump said it would be “a long time” before the United Stateswould talk to the group.

“We’re going to finish what we have to finish,” he told reporters. “Whatnobody else has been able to finish, we’re going to be able to do it.” TheWashington Post