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Taliban fighters brandished Kalashnikovs and shook their fists in the air after the Sept. 11 terrorist attacks, defying American warnings that if they did not hand over Osama Bin Laden, their country would be bombed to smithereens.

The bravado faded once American bombs began to fall. Within a few weeks, many of the Taliban had fled the Afghan capital, terrified by the low whine of approaching B-52 aircraft. Soon, they were a spent force, on the run across the arid mountain-scape of Afghanistan. As one of the journalists who covered them in the early days of the war, I saw their uncertainty and loss of control firsthand.

It was in the waning days of November 2001 that Taliban leaders began to reach out to Hamid Karzai, who would soon become the interim president of Afghanistan: They wanted to make a deal.

“The Taliban were completely defeated, they had no demands, except amnesty,” recalled Barnett Rubin, who worked with the United Nations’ political team in Afghanistan at the time.

Messengers shuttled back and forth between Mr. Karzai and the headquarters of the Taliban leader, Mullah Omar, in Kandahar. Mr. Karzai envisioned a Taliban surrender that would keep the militants from playing any significant role in the country’s future.

But Washington, confident that the Taliban would be wiped out forever, was in no mood for a deal.

“We don’t negotiate surrenders,” Secretary of State Donald Rumsfeld said in a news conference at the time, adding that the Americans had no interest in leaving Mullah Omar to live out his days anywhere in Afghanistan. The United States wanted him captured or dead.

Almost 20 years later, the United States did negotiate a deal to end the Afghan war, but the balance of power was entirely different by then — it favored the Taliban.

For diplomats who had spent years trying to shore up the U.S. and NATO mission in Afghanistan, the deal that President Donald J. Trump struck with the Taliban in February 2020 to withdraw American troops — an agreement President Biden decided to uphold shortly after taking office this year — felt like a betrayal.

Now, with the Taliban back in power, some of those diplomats are looking back at a missed chance by the United States, all those years ago, to pursue a Taliban surrender that could have halted America’s longest war in its infancy, or shortened it considerably, sparing many lives.

For some veterans of America’s entanglement in Afghanistan, it is hard to imagine that talks with the Taliban in 2001 would have yielded a worse outcome than what the United States ultimately got.

“One mistake was that we turned down the Taliban’s attempt to negotiate,” Carter Malkasian, a former senior adviser to Gen. Joseph Dunford, who was chairman of the Joint Chiefs of Staff during parts of the Obama and Trump administrations, said of the American decision not to discuss a Taliban surrender nearly 20 years ago.

“We were hugely overconfident in 2001, and we thought the Taliban had gone away and weren’t going to come back,” he said. “We also wanted revenge, and so we made a lot of mistakes that we shouldn’t have made.”

Little more than a year later, the United States would bring the same air of confidence, and unwillingness to negotiate, to its invasion of Iraq, opening another war that would stretch long past American predictions.

By the time the Trump administration reached a deal with the Taliban, the United States was exhausted by war, with little leverage given that it had announced its intention to leave Afghanistan. Nearly 2,500 Americans had died fighting on Afghan soil, along with almost 1,000 troops from allies like Britain and Canada.

The toll for Afghans has been far higher: At least 240,000 Afghans have died, many of them civilians, according to the Watson Institute at Brown University. By some estimates, American taxpayers had spent nearly two trillion dollars on the effort, with few assurances of anything lasting to show for it.

The Taliban, by contrast, went into the negotiations far stronger than before. Their safe haven in Pakistan, to which they had fled in 2001, had turned into a supply line. And even at the height of the American troop presence, the insurgents were able to keep a growing stream of recruits coming both from Afghanistan and Pakistan, fueled in part by rising profits from the opium trade.

They eventually controlled much of Afghanistan, moving first into rural areas and then poking at cities, occasionally dominating the streets for a few days and then fading back into the countryside. Deaths of Afghan security forces increased, sometimes rising to hundreds in a week.

“When I heard the U.S. were going to meet in Doha with the Taliban and without the Afghan government, I said, ‘That’s not a peace negotiation, those are surrender talks,’” said Ryan Crocker, a former ambassador to Afghanistan.

“So, now the talks were all about us retreating without the Taliban shooting at us as we went,” Mr. Crocker added, “and we got nothing in return.”

The deal the Trump administration struck did not enshrine rights for women, nor guarantee that any of the gains the United States had spent so many years, and lives, trying to instill would be preserved. Nor did it keep the Taliban from an all-out military push to take over the country.

It was not even a peace deal. Instead, it extracted a somewhat vague promise by the Taliban to prevent future attacks against the United States and its allies. And even that language was contested: In the agreement, the Taliban refused to accept the word “terrorist” to describe Al Qaeda.

Now, the Taliban control the country again, are hunting down Afghans who worked with or fought alongside the United States, are violently suppressing protests and, even as they promise to allow women to participate in society, are again starting to limit women’s roles outside the home in some parts of the country.

In short, much that the United States tried to put in place is already at risk of being erased.

Some former diplomats point out that the war did bring tangible improvements. U.S. Special Operations Forces used Afghanistan as a staging point to target Osama Bin Laden, leading to his death in Pakistan in 2011. On the civilian side, the American-led effort brought education to millions of Afghan boys — and, vitally, to many girls. Afghans got cellphones and embraced social media, allowing many of them to see and communicate with the rest of the world.

But from a national security standpoint, once Bin Laden was dead, the strategic reason for the United States to stay in the country declined considerably — a rare point of policy upon which presidents Barack Obama and Donald J. Trump agreed.

There were certainly other barriers to peace talks 20 years ago. At that time, the Pentagon smoldered for days after the 9/11 attackers crashed their plane into the west side of the building, and the World Trade Center lay in ruins, a vast pile of twisted metal and concrete. The sense of a national grief, humiliation and anger was palpable, bringing a passion for revenge that may have also blinded many American officials to the long history of failed invasions and occupations in Afghanistan.

On Sept. 11, 2001, Richard Armitage, then the No. 2 person at the State Department, told the head of the Pakistani military’s Inter-Services Intelligence agency that Pakistan was either on America’s side or would be considered an enemy: “It’s black or white,” he said in an interview for PBS in which he recalled the conversation.

Mr. Armitage said that Gen. Mahmood Ahmed, then the I.S.I. chief, had started to explain how the Taliban had come into existence, their history and relationships in Afghanistan — including many who had helped in the U.S.-aided resistance to the Soviet occupation. Mr. Armitage cut him off: “I said, ‘No, the history begins today.’”

Barely two weeks after Mr. Rumsfeld torpedoed Mr. Karzai’s efforts to find a negotiated end to the fighting, a conference began in Bonn, Germany, to plan a successor government in Afghanistan, without the Taliban.

That process further sealed the Taliban’s role as outsiders — all but ensuring that any efforts to reach a deal with them would be rejected. Most of those invited to the conference were expatriates or representatives of the warlords whose abuses of Afghan civilians in the 1990s had led to the Taliban’s takeover of the country in the first place.

“At the time, there was no discussion of Taliban inclusion,” said James Dobbins, one of the American diplomats at the meeting.

“Frankly, if the Taliban had been invited, no one else would have come,” he said, adding that, in retrospect, “We should have figured the Taliban into the calculation.”

Lakhdar Brahimi, the United Nations special envoy for Afghanistan, was adamant that although the Taliban had been left out of Bonn, they should at least be included in the next step in forming a transitional government: a loya jirga, bringing together tribes, sub-tribes and other groups to determine the country’s way forward.

A few people close to the Taliban ideologically, but not part of the group, brought binders with their nominees’ resumes to a United Nations office where rising Afghan leaders were reviewing potential representatives. But some of the potential representatives were dismissed as terrorists and later detained, and one was shipped to the U.S. detention camp at Guantánamo Bay, where he spent more than six years even though he had never supported the Taliban, Mr. Rubin said.

“A number of Afghans with the Taliban offered to surrender and, when they did, we put them in prison, in Bagram and Guantánamo, and there was never any discussion if that was a good idea,” recalled Mr. Dobbins, who worked with the transitional Afghan government.

At the time, he said, “I was dismissive of the idea that the Taliban would ever be a factor in postwar Afghanistan. I thought they had been so beaten and brushed aside that they would never come back.”

Looking back, he said: “I should have known. But what we didn’t understand, didn’t pick up on for five years, was that Pakistan had abandoned the Taliban government, but had not abandoned the Taliban. That was a critical distinction. So they could re-recruit, re-fund, re-train and project themselves back into Afghanistan. That was a major missed opportunity.”

While it is not clear that a deal with the Taliban in 2001 would have been possible — or that the Taliban would have kept their word — some former diplomats say that by repeatedly shutting the door to talks, the United States may have closed off its best chance of avoiding a prolonged and extremely costly war.

“It’s true that it was completely unclear how real those attempts were or if they were the real representatives of Mullah Omar,” said Mr. Malkasian, the former adviser to the Joint Chiefs of Staff. “But in a peace deal, you have to include the defeated party — that’s how you negotiate.”

“Even if they represented only one Taliban, you have to ask: Why did we turn it down?” he said.

In those early days, I remember how quickly the Taliban went from imperious to almost apologetic. I was one of a group of journalists whom, in late November 2001 — only weeks before they were driven from power — they invited into the country to project the appearance of still being in control.

But they weren’t, and it was apparent. They did not even control the territory they nominally held, and were unable to guarantee our safety in the Afghan border town of Spin Boldak. When an anti-Western crowd pelted our cars with stones, breaking my windshield, they were helpless to stop them.

The Taliban sent us back to Pakistan after three days of being penned inside their compound, because they feared that if they let us wander, they could not protect us. Their authority was waning, their chapter almost over.

Or so it seemed.


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