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By 2008 the fighting had morphed into a full-blown insurgency. The United Nations used to issue security maps for aid workers on which green marked safe areas and yellow those areas with some security problems, and red was used for dangerous areas under insurgent control. By 2008 large areas of the maps were in red. Many Afghans thought that the Taliban looked poised for victory, and when it comes to insurgencies, what the locals think often dictates the outcome. One Western observer back from Kabul in mid-2008 said every shopkeeper in the city (the most well-protected part of Afghanistan) thought that Taliban fighters would be in the capital by the year’s end. Afghanistan was fast slipping into chaos.

Everything about Afghanistan was a challenge—its rugged geography, its convoluted ethnic makeup, labyrinthine social structure, and jealous tribalisms, its byzantine politics, and the bitter legacy of decades consumed by war and occupation. But the biggest problem lay across the border: Pakistan.

The Taliban operated out of the FATA, but its leadership had set up shop farther south in Quetta. They used the Pakistani city’s relative safety to regroup and orchestrate the insurgency in Afghanistan. Taliban commanders recruited foot soldiers from seminaries across Pakistan’s Pashtun areas and ran training camps, hospitals, and bomb-making factories in towns and villages a stone’s throw from the Afghanistan-Pakistan border.

Moreover, since the Taliban’s formation in 1994 the insurgent organization has maintained close ties with Pakistan’s intelligence agency and received financial and military support from Islamabad. Pakistani support sustained Taliban military offensives throughout the 1990s, and even after the U.S. offensive broke the Taliban’s hold on Afghanistan that relationship continued.

Pakistan has viewed the Taliban as a strategic asset that could keep India out of Afghanistan and under Pakistan’s control. That makes the Afghan insurgency a regional problem. It is hard enough to fight an insurgency, but one that has a safe haven to retreat to within a sympathetic population and can rely on the financial, intelligence, and military support of a neighboring country is a tougher challenge still, by orders of magnitude. The Taliban and al-Qaeda would fight in Afghanistan, and when things got too hot, they would hasten south across the border to tend their wounds, recruit and train fresh fighters, and plan for more war. Indeed, the collective leadership of the Taliban became popularly known as the Quetta Shura, after the city where it met. The Afghanistan fight was starting to eerily resemble Vietnam, with Pakistan acting roughly like Laos, Cambodia, and Maoist China all rolled into one. The war was taking on a new, expensive shape, one that needed urgent attention.

By the time President Obama moved into the Oval Office, the Taliban juggernaut looked unstoppable. They had adopted a flexible, decentralized structure that reported to the leadership in Pakistan, but organized locally. There was a national political infrastructure in place too, with shadow governors and district leaders for much of the country. In some cases, this Taliban presence was nominal—the Taliban are almost exclusively a Pashtun phenomenon and do not reach into every corner of multiethnic Afghanistan—but elsewhere the Taliban were in control.

The Taliban had a strength that belied their numbers. The U.S. government estimated that in 2009 the Taliban were no more than 35,000 strong. Of these, only a core of at most 2,000 were battle-hardened veterans of Afghanistan’s earlier wars. A larger number, maybe 5,000 to 10,000, were in the fight to avenge government abuse or the death of kith and kin in U.S. raids and aerial bombings. The largest number of fighters, 20,000 or more, were mercenaries, in it for a few dollars a day.

The Taliban had become politically more savvy and militarily more lethal.7 Gone was their objection to pictures and music, and in came the use of both in their recruiting videos. In their statements, the new Taliban claimed to be open to women going to school. Talk of chopping off hands and lopping off heads in public was put aside.

Other beliefs, more ominously, were put aside as well. Steve Coll, the journalist and longtime observer of Afghanistan, writes that in the 1980s, when Afghan warriors were battling Soviet occupation, the CIA was desperately seeking someone to set off a massive vehicle bomb inside the 1.6-mile-long Salang Tunnel. The tunnel is a crucial north-south link running beneath a difficult pass in the towering Hindu Kush mountain range, and blowing it up would have cut the main Soviet supply route. In order to be effective, the bomb would need to go off mid-tunnel, meaning certain death for its operator. In effect, the CIA was looking for an Afghan suicide bomber.8 No one volunteered. Suicide, said the Afghans, was a grievous sin, and quite against their religion. And yet, fast-forward to 2009, and there had been more than 180 suicide bomb attacks in Afghanistan.9 The Taliban had evolved to make Afghanistan an even more dangerous place.

Shortly after he took office, President Obama appointed Richard Holbrooke as his point man on Afghanistan—his special representative—to help him quickly gauge the situation in that country and come up with a strategy to deal with it. At the time the military was urgently lobbying the new president for more troops, needed to hold the line against the Taliban while Washington thought through the problem. Obama asked for a quick strategy review—a quick read of the situation—and tapped former CIA and Clinton White House Pakistan point man Bruce Riedel to lead the effort.10 The review took sixty days, and its findings (popularly known as the Riedel Report) argued for beefing up American troop presence in Afghanistan, “fully resourcing” counterinsurgency operations there, and getting tough with Pakistan. Holbrooke, who served on Riedel’s commission, disagreed. He did not favor committing America to fully resourced counterinsurgency and thought America would get more out of Pakistan through engagement.

Riedel met the president alone to brief him on his report’s findings. Holbrooke thought the president should have heard from more people. Absent a proper debate on the report’s findings and recommendations, thought Holbrooke, the president moved too quickly to deepen the war.

In February 2009, Obama announced that he was sending 17,000 more troops to Afghanistan, buying enough time for the president and his advisers to determine their next steps. Soon after, he also asked his commander in Afghanistan, General Stanley McChrystal, to review the war strategy and outline what we needed to do to win.11 As General McChrystal prepared his review, the National Security Council (NSC) pulled together facts, figures, opinion, and analysis from across the government (mostly from the Pentagon, State Department, CIA, and U.S. Agency for International Development) in order to prepare the president to evaluate McChrystal’s recommendations. The goal was to place before President Obama a set of clear options from which he could choose.

The Obama administration was facing a bedeviling two-headed problem. Even as the Taliban were regrouping and growing more formidable, our local partner, the Karzai government, was proving to be weak and ill suited for the task of democracy building.12 The shine had come off Hamid Karzai even before Obama took office. In the administration’s and Congress’s minds the smartly dressed, enlightened leader of a new Afghanistan had somewhere along the line been reduced to a venal, corrupt, and unreliable partner, and as such a chief reason why the Taliban were doing so well. Whatever the “new” Afghanistan was supposed to look like, in the real, existing Afghanistan, clans and extended families mattered. Karzai’s clan, unfortunately, looked a lot like the Sopranos. The president’s brother Ahmad Wali was actually the fixer in Kandahar, a Taliban stronghold. He worked notoriously with both the CIA and the Taliban and had his hand in every deal and all the political wrangling in that wayward city. Karzai also patronized an array of corrupt local grandees with ties to the drug trade. They bolstered his rule and he gave them the means to line their pockets while abusing the local population.13