One evening in June 2009, Richard Holbrooke paid a visit to Pakistan’s President Asif Ali Zardari at the presidential palace in Islamabad. It was one of his first visits to the region as the Obama Administration’s special representative to Afghanistan and Pakistan. In that role, Holbrooke — who died in December 2010 — wanted to broaden and deepen engagement with the country many had come to see as the most dangerous place in the world. And Zardari had his own ideas about how Washington could help.

“Pakistan is like AIG,” Zardari told Holbrooke, comparing his country to the U.S. insurance giant that was bailed out in 2008. “Too big to fail.” Washington, Zardari keenly recalled, had given AIG “$100 billion. You should give Pakistan the same,” Zardari said. Holbrooke smiled throughout the meeting.

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Sitting with Holbrooke was Vali Nasr, then his senior adviser. Nasr recalls the episode in his new book, The Dispensable Nation: American Foreign Policy in Retreat, a searing critique of how the Obama Administration has been too timid to transform American foreign policy. Holbrooke, writes Nasr, was troubled by Zardari’s display of dependence on the U.S. and the sense of entitlement that went with it. “Holbrooke didn’t like the image of Pakistan holding a gun to its own head as it shook down America for aid,” writes Nasr, now dean of the Paul H. Nitze School of Advanced International Studies at Johns Hopkins University.

Holbrooke did agree, however, with Zardari that Pakistan was important and the U.S. had a long-term interest in its stability. For the next year and a half, Holbrooke and his team pursued a policy of diplomatic engagement with Pakistan. It went beyond the traditional approach narrowly based on security concerns. The idea was to try and address Pakistan’s strategic calculus — an ambitious target that may have underestimated how far Pakistan was willing to go without changing its ways. “What Holbrooke wanted,” Nasr tells TIME in an interview, “was to engage big and try and change the course of this country and its relationship with Washington once and for all.”

But from the very start, President Barack Obama and the White House never really bought into the idea. “The White House tolerated Holbrooke’s approach for a while,” Nasr writes in the book, “but in the end decided that a policy of coercion and confrontation would better achieve our goals in Pakistan.” Washington was less interested in working with Pakistan, Nasr says, than pressuring it into compliance. That strategy, he says, has failed. And now, he warns, the U.S. risks pivoting away from the region at the cost of abandoning vital interests that remain there.

“When you look at Pakistan today,” says Nasr, “it is nuclear-armed, in near conflict with India, has a dangerous civil war with its own extremists, is now subject to one of the most brutal terrorism campaigns against its population, that is now coming apart along sectarian lines.” If the U.S. does not maintain influence in Pakistan, he says, it won’t be able to have a positive impact on the direction of the country. “Looking at it from an American perspective,” Nasr says, “we’re just going to be basically saying, ‘We’re going to sit on the sideline and look at this roller coaster go off this rail.’”

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Holbrooke’s approach was ambitious. A strategic dialogue was established between the two countries. Nonmilitary aid was tripled. Washington began to reach out to civilian centers in Pakistan for the first time. “There was a discussion on energy and electricity and water and women,” says Nasr. “These were ways of laying out for Pakistan a longer road map with the U.S., and alternately trying to put on the table for Pakistan interests that would gradually wean it away from its strategic outlook and bring it in a new direction.” There would be no quick fix. It was a longer strategy aimed at slowly undoing decades of alienation and mistrust.

In the first two years, Nasr insists that there were rewards. The U.S. got more intelligence cooperation, he details in the book. “More agents, more listening posts, and even visas for the deep-cover CIA operatives who found [Osama] bin Laden.” Long-strained relations between Islamabad and Kabul improved enough for it to help U.S. counterinsurgency efforts in Afghanistan. The Pakistanis also finally moved against the Pakistani Taliban in the Swat Valley and South Waziristan, in military offensives that helped the war across the border. “The Pakistanis didn’t cooperate 100%,” says Nasr. “But they did cooperate 50%.”

But the Obama Administration didn’t have the patience to stick with it. As Nasr acknowledges, there was a rival school of thought that said, “It was too difficult, too time-consuming and wouldn’t work anyway.” When Holbrooke died, their view won out. Nasr resigned from the State Department soon after. In 2011, three major incidents brought the relationship crashing to its lowest-point ever: a CIA contractor, Raymond Davis, allegedly killed two people in Lahore; U.S. Navy Seals carried out a raid to get Osama bin Laden without informing the Pakistanis; and toward the end of the year, 26 Pakistani troops were killed in a cross-border incident.

The security relationship, Nasr says, worked better when there were other efforts alongside it. “The Pakistanis said, ‘O.K., you have security interests. We have economic interests and we have civilian interests,’” recalls Nasr. “We always got much further with the Pakistanis in those first two years when the conversation was not just about drones and terrorists, but it was also about energy and water.”

The CIA and the Pentagon saw the benefits of the cooperation, Nasr notes in his book. But at the same time, he writes, they applied constant pressure that “threatened to break up the relationship.” At one point, Holbrooke turned to him, shaking his head, and said: “Watch them [the CIA] ruin this relationship. And when it is ruined, they are going to say, ‘We told you, You can’t work with Pakistan!’ We never learn.”

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