U.S. envoy to Afghanistan faces greatest challenge - and an unpredictable president

A Republican with decades of diplomatic experience, he hadn't disqualified himself by speaking out about the president. A polyglot Afghan native, he was a skilled bureaucratic operator with clout in the halls of Washington and the craggy peaks of the Hindu Kush. 

Those qualities appear to have played a meaningful role in clinching last month's landmark deal with the Taliban, a milestone after two decades of war. 

But it's uncertain whether they will prove decisive in the next, more difficult phase of negotiations, which will include a fractious group of Afghans and entail an unpredictable, potentially destabilizing role for Trump. 

Khalilzad is expected to be closely involved when representatives from the Taliban, the Afghan government and Afghan society sit down as early as this week to begin mapping out a future governing structure and finding consensus on divisive issues such as the role of Islam and women's rights. 

There are signs of trouble. Afghan and Taliban leaders are disputing the terms of Khalilzad's initial deal, and the militants have launched deadly attacks. The format, objectives and even precise location of the next negotiations remain a mystery. 

"This is his biggest challenge," said Carter Malkasian, a former Pentagon official who took part in some of the talks Khalilzad conducted with militant leaders over the past two years. "This negotiation is much more difficult than what we've done up to now, including in political terms for the United States." 

Looming over the negotiations is officials' hazy understanding of what Trump wants and will tolerate. While the president has consistently voiced his desire to get troops out of the country, it is less clear how he will define American interests in what will probably be a protracted effort to shape Afghanistan's future. 

"Countries have to take care of themselves," Trump said this week as officials scrambled to keep the negotiating process on track, referring to the 18-year American effort that has cost more than $900 billion and more than 2,000 American lives. "You can only hold someone's hand for so long." 

Khalilzad's unlikely path to becoming a high-wattage American diplomat began in the city of Mazar-e Sharif, which, like most of Afghanistan in the early 1950s, was an undeveloped place. 

In Mazar-e Sharif, children went to school on horseback. There was no radio station or sewage system, and health services were poor. His father, a civil servant, married Khalilzad's mother when she was between age 9 and 12, Khalilzad wrote in his autobiography. She gave birth 13 times; six of those children died.

As a teenager, Khalilzad, along with current Afghan President Ashraf Ghani, secured what would become a life-changing opportunity when he was selected to spend a year in the United States as an exchange student. He saw his first television set and rode in an elevator for the first time. 

Khalilzad rose quickly through the Republican foreign policy world, joining the State Department in the 1980s after completing a PhD at the University of Chicago. By the time George W. Bush's administration launched a military campaign against the Taliban in response to the Sept. 11, 2001, attacks, Khalilzad was already an important voice on Afghanistan policy. 

In December of that year, Khalilzad served as a top aide at the Bonn conference, designed to give shape to Afghanistan's post-Taliban state. Khalilzad had relationships with the main Afghan players and, like no other U.S. diplomat, could call up warlords on their satellite phones to cajole or coerce them. As U.S. ambassador in Kabul from 2003-2005 and Baghdad from 2005-2007, he helped oversee America's attempts to stabilize nations upended by war. 

But Afghanistan's conflict continued, year after year. By the time Khalilzad joined the Trump administration in the fall of 2018, Trump had grudgingly approved sending more troops to Afghanistan. Military leaders, long suspicious of cutting a deal with their enemy, had slowly warmed to negotiations as they concluded that nothing - not troops surges or a succession of commanders and strategies - would bring a Taliban defeat. 

From the start, Khalilzad's approach reflected his brand of vigorous, sometimes improvisational diplomacy. In Kabul, he took walks with Ghani, seeking to mollify the Afghan leader's fears that Washington would leave his government in the lurch. In the Qatari capital, where militant negotiators were based, he would often pull Mullah Abdul Ghani Baradar, a senior Taliban official, aside for one-on-one conversations. Sitting down for lunch shared by American officials and the Taliban, the Afghans would switch to speaking Pashto, and the room would erupt in laughter, according to former officials, who spoke on the condition of anonymity to describe sensitive negotiations. 

While officials saw the power of Khalilzad's background and relationships, some accused him of glossing over or liberally wheeling and dealing with U.S. interests in his haste to clinch a deal. 

To some in Washington, those criticisms were compounded by Khalilzad's ties to shadowy figures or rumors that he considered running for Afghan president a decade ago, making him what one person with knowledge of the talks described as a "charming scoundrel. "

Secretary of State Mike Pompeo proved critical in providing political cover for Khalilzad in Washington as he explored new ways to forge a deal with the Taliban. Pompeo had urged Trump to send more troops to Afghanistan early in the administration but came to accept the need to reduce the U.S. role in the conflict. Pompeo began using his formidable influence - and the perception that it curried the wishes of the president - to allow his envoy to stake out previously taboo positions.

Officials close to Pompeo say he knew Trump viewed withdrawal as a priority. While the idea of a military departure contradicted the secretary's hawkish instincts, he began viewing the arguments against leaving as outdated "establishment thinking." 

Pompeo approached the talks asking, "If you're opposed to withdrawal, what's your alternative? Keep American troops there another 10 years? Another 20?" a senior administration official said. "He sees some critics as lacking any workable plan."

In one important shift, Khalilzad was permitted to jettison an Obama administration-era requirement that the Afghan government take part in talks from the beginning, a position that had stymied progress for years.

Crucially, Khalilzad was able to offer, for the first time, a full withdrawal of American troops, a move that reflected not only Trump's core desires but also the possibility that the president might lose patience and abruptly order a pullout, as he had in Syria. 

"Zal's willingness to rip up the failed negotiating playbook of the past and try new approaches" was significant in getting to this point, one U.S. official said, using the name Khalilzad commonly goes by. 

Some officials, especially at the Pentagon, believed Khalilzad was making dangerous concessions, especially in regards to counterterrorism. They doubted his gamble that the Taliban would follow through on a vow to break with al-Qaida and keep the Islamic State's Afghan branch in check. 

"His answer to CT was the Taliban dealing with it, which was magical thinking," one former official involved in the negotiations said, using an acronym for counterterrorism programs. 

Despite those concerns, Pentagon leaders fell in behind the deal after the resignation in late 2018 of Defense Secretary Jim Mattis, who was one of the few senior officials who seemed as if they might take a forceful stance against aspects of the deal. Khalilzad became, as one former senior military leader described him, "the only horse on the track."

"It might look at times like he's giving away too much," said Malkasian, the former Pentagon official. "But people should not distrust his ultimate goal." 

Current and former officials remain divided on the merits of the deal, but many of them credited Khalilzad for having navigated an administration devoid of regular interagency coordination and overshadowed by the uncertainty created by the president's often contradictory positions. 

Khalilzad succeeded in getting latitude and support "from an otherwise fairly divided, not particularly well-organized administration," said James Dobbins, a veteran former diplomat who was Khalilzad's chief at the Bonn conference in 2001. "He showed remarkable perseverance." 

Facing opposition to a full withdrawal from then-national security adviser John Bolton, Pompeo held small meetings that included CIA Director Gina Haspel and Patrick Shanahan, the acting defense secretary at the time, as Khalilzad sought to push forward.

The effort nearly came off the rails several times, including in January 2019 before the State of the Union address, which U.S. negotiators feared Trump might use to announce a troop withdrawal. 

Pakistan had suggested that Khalilzad meet with a different set of Taliban representatives, but after several days of U.S. officials waiting in Islamabad, Pakistani officials said they couldn't produce the group. So Khalilzad flew to Doha, Qatar, where he pushed ahead on staking out a possible deal with the Taliban's primary negotiating team. That allowed Pompeo to relay to Trump that they were making real progress, which the president cited in his address. 

How those dynamics will affect Khalilzad's prospects for helping reach a durable Afghan settlement is less clear. 

Already there are suggestions that Khalilzad's ability to finesse differences among Afghans is limited. A day after officials heralded the U.S.-Taliban deal in Doha and Kabul, Ghani publicly rejected one of its central points, a commitment that the Afghan government would release up to 5,000 Taliban prisoners before the start of the Afghan-to-Afghan talks.

Compounding the challenge ahead may be political pressure to execute the U.S. troop withdrawal on an agreed 14-month timeline, despite provisions allowing Washington to halt or reverse that if the Taliban doesn't uphold its side of the deal. That may be especially true as Trump heads into a reelection battle, again making the president's wishes an unpredictable element of Khalilzad's diplomatic test. 

"Before, the main thing Zal needed to do was to convince Trump to make concessions, then go into the room and play the string out as a negotiator," said Jarrett Blanc, who took part in discussions with the Taliban during the Obama administration. "Now, it's more complicated." 

Even Khalilzad's supporters acknowledge the meager odds of achieving a lasting peace for a nation locked in a seemingly endless conflict. "The Afghans might not be prepared to set aside their differences and make peace," the U.S. official said. "But fighting for another 18 years isn't a winning strategy either."