Four days after the United States invaded Afghanistan, President George W. Bush appeared in the East Room of the White House for a prime-time news conference to address a nation gripped by fear and anger about the 9/11 attacks. Although most Americans supported Bush’s decision to go to war, there was widespread uncertainty about how the conflict would unfold and how long it might last.

Bush, then 55, had been in office for less than nine months. That evening, on Oct. 11, 2001, he sought to reassure the country that U.S. officials had learned hard lessons from the past and that they were determined not to get bogged down in an ill-defined war in a faraway land.

“We learned some very important lessons in Vietnam,” Bush said. “This is a different kind of war that requires a different type of approach and a different type of mentality.”

As for the expected duration of the war, Bush offered no definitive answers but flatly promised to win. “This particular battle front will last as long as it takes to bring al-Qaida to justice,” he declared. “It may happen tomorrow, it may happen a month from now, it may take a year or two, but we will prevail.”

But from the outset, the U.S. government never defined the terms of victory. On Wednesday, President Joe Biden prepared to announce the complete withdrawal of U.S. troops by September. Still unresolved is the question of what kind of outcome his three predecessors in the White House envisioned when they repeatedly pledged to win the war.

At first, the objective was to destroy al-Qaida and ensure that the terrorist group could not use Afghanistan as a base to launch another terrorist attack on the United States. But within six months, that goal had been accomplished. Al-Qaeda’s leaders had either been killed, captured or had fled Afghanistan.


Rather than declare the war over, Bush broadened the mission. In April 2002, he announced new military and political objectives.

The United States, he said, would help its Afghan allies build a modernized nation, with a stable democracy, a strong national army, better medical care, and a new system of public education for boys and girls alike. “We know that true peace will only be achieved when we give the Afghan people the means to achieve their own aspirations,” he said in a speech at the Virginia Military Institute.

Although the goals were noble and high-minded, Bush offered no benchmarks for achieving them and gave no indication of how long U.S. troops would have to remain. “We will stay until the mission is done,” he said.

The next two commanders in chief of the war, Barack Obama and Donald Trump, put themselves in the same bind. Like Bush, they vowed to win in Afghanistan, raising expectations of a decisive military victory over a vanquished enemy.

But they neglected to specify what that meant or what U.S. troops would have to accomplish before they could come home. They also never clearly identified whom the United States was trying to defeat. Was the enemy al-Qaida? Or also the Taliban? And what about the myriad other armed factions in Afghanistan that threatened to disrupt the country?

Army Gen. Dan McNeill, who served two stints as the commander of U.S. troops in Afghanistan during the Bush years, said the endgame was always opaque.


“I tried to get someone to define for me what winning meant, even before I went over, and nobody could,” McNeill later told government interviewers. “Some people were thinking in terms of Jeffersonian democracy, but that’s just not going to happen in Afghanistan.”

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As the war dragged on, U.S. officials kept insisting publicly that they were winning — even in the face of mounting evidence to the contrary. In private, however, they expressed serious doubts.

“Are we winning or losing the Global War on Terror?” Defense Secretary Donald H. Rumsfeld wrote in a confidential memo to several top Pentagon officials in October 2003. He concluded by saying, “It is pretty clear that the coalition can win in Afghanistan and Iraq in one way or another, but it will be a long, hard slog.”

By 2006, as the Taliban steadily regained strength and escalated its guerrilla campaign, the doubts became more severe.

“We are not winning in Afghanistan,” U.S. Ambassador Ronald E. Neumann warned officials in Washington in a diplomatic cable on Aug. 29, 2006. He added that there was “a broad Afghan perception that victory is slipping away.”

Yet in public, U.S. officials continued to declare the opposite.


“We are winning,” Lt. Gen. Karl Eikenberry, the commander of U.S. forces in Afghanistan, told ABC News just two weeks after Neumann wrote his pessimistic cable. Asked whether the United States could lose the war, Eikenberry responded: “Losing is not an option in Afghanistan.”

Two years later, U.S. field commanders pleaded with the Pentagon for reinforcements because they were losing ground to the Taliban, which they estimated had grown in strength to 7,000 to 11,000 fighters. But U.S. military officials struggled to reconcile their requests for troops with their repeated assurances of victory.

In September 2008, Army Maj. Gen. Jeffrey Schloesser, the commander of U.S. forces in eastern Afghanistan, was pressed by reporters on whether he thought his soldiers were still winning. “Let me just say that we’re not losing a war out here, by any means,” he said. “It’s a slow win, I guess.”

By the time Obama took office in 2009, U.S. military officials acknowledged that they were facing a worsening insurgency. The new president announced an expansive strategy to send thousands of additional troops to Afghanistan and spend tens of billions of dollars to build up the still-wobbly government in Kabul. “To the terrorists who oppose us, my message is the same: We will defeat you,” Obama said in March 2009.

Once again, however, no one in his administration could articulate what winning meant.

“How are we going to know when this is over? How does this end?” Sen. James Webb, D-Va., asked Michèle Flournoy, Obama’s undersecretary of defense for policy, and Army Gen. David Petraeus at a congressional hearing in April 2009.


Flournoy gave a complicated and long-winded answer.

“I think that a key point of defining success is when both the Afghans and the Pakistanis have both the capability and the will to deal with the remaining threat themselves — that the period of extraordinary intervention and assistance comes to a transition point and we go to a more long-term, normal development assistance relationship with both countries,” she said. “To me, it is when that — when they — when we have reduced the threat and built that capacity locally to the point where they can be much more self-reliant in managing this problem.”

Petraeus added, “Well, I guess I’d echo that.”

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Obama administration officials became entangled in other contradictions. On one hand, they began to acknowledge that an outright military victory was unlikely and that the only practical way to end the conflict was for Afghanistan’s warring parties to reach “a political solution.”

On the other hand, as the number of U.S. troops reached 100,000, Obama’s generals kept trying to bludgeon the Taliban into submission instead of encouraging diplomacy.

“Our argument was that we only have the insurgency because we don’t have a political settlement. And if we don’t address it, the military won’t be able to,” Barnett Rubin, a senior State Department adviser, later told government interviewers. But Rubin added that officials at the Pentagon and the CIA saw little reason to negotiate with the Taliban and defined reconciliation as “we’ll be nice to people who surrender.”

In public, some Obama administration officials began to hedge their bets.

At a congressional hearing in June 2011, Defense Secretary Robert Gates was asked whether the United States was winning or losing in Afghanistan.


“I have learned a few things in 4 1/2 years,” he replied. “And one of them is to try and stay away from loaded words like ‘winning’ and ‘losing.’ What I will say is that I believe we are being successful in implementing the president’s strategy.”

A week later, at another congressional hearing, Secretary of State Hillary Clinton walked the same fine line.

“I don’t think it’s a matter of winning or losing,” she said. “It think it’s a matter of how we measure the success we are seeking in Afghanistan.”

But, as with the terms of victory, nobody defined success with any specificity.

Obama’s strategy hinged on his plan to train and equip an Afghan security force of 352,000 troops and paramilitary police who could take over the fighting from U.S. forces. For most of Obama’s presidency, his commanders expressed complete confidence in the approach and predicted that Afghan forces would win the war with U.S. help.

In February 2013, Marine Gen. John Allen, the outgoing commander of U.S. and NATO troops, promised that Afghan forces were ready to take control of the fighting. “This is victory,” he said. “This is what winning looks like. And we should not shrink from using those words.”


Other generals adopted a similar bravado.

“I talk a lot about winning these days and I firmly believe that we’re on a path to win,” Marine Gen. Joseph Dunford Jr., Allen’s successor, said at a military ceremony in Kabul in May 2013.

Dunford’s deputy, Army Lt. Gen. Mark Milley, echoed his boss at the ceremony when he addressed Afghan troops on the parade ground.

“You will win this war and we will be there with you every step of the way,” said Milley, who now serves as chairperson of the Joint Chiefs of Staff. He proclaimed that they were “on the road to victory, on the road to winning, on the road to creating a stable Afghanistan.”

Obama pledged to withdraw all U.S. forces from Afghanistan by the end of his second term. But he reversed himself and ordered about 8,400 troops to remain when it became apparent that the Afghan security forces were incapable of fending off the Taliban on their own.

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By the time Trump moved into the White House in 2017, things looked bleak. The Taliban had grown more powerful — not weaker — during Obama’s eight years in office, accumulating an estimated 60,000 fighters under its command. The Afghan army and police were taking so many casualties that the government in Kabul kept the numbers a secret to avoid destroying morale.

“We are not winning in Afghanistan right now,” Jim Mattis, Trump’s defense secretary, acknowledged to the Senate Armed Services Committee in June 2017.


Such gloomy talk infuriated Trump, who made clear to the Pentagon that he would not tolerate defeatist rhetoric.

In August 2017, he announced his own new war strategy. In a speech at Fort Myer in Virginia, he vowed not just to end the 16-year-old conflict, but to win it — once and for all.

“Our troops will fight to win,” Trump said. “From now on, victory will have a clear definition: attacking our enemies, obliterating ISIS, crushing al-Qaida, preventing the Taliban from taking over Afghanistan, and stopping mass terrorist attacks before they emerge.”

Trump re-escalated the war by raising U.S. troop levels to 14,000. He also ordered an intensive campaign of airstrikes that dropped more bombs and fired more missiles than at any other time in the conflict.

But Trump wasn’t really banking on an outright military victory.

Under his strategy, U.S. forces were simply trying to weaken the Taliban to gain political leverage for peace talks. In February 2020, the Trump administration reached a deal with the Taliban that set the stage for the gradual withdrawal of all U.S. troops from the country.

That finally stopped all the promises that the United States would win the longest war in its history.