The vote against funding. On May 20, 2009, as part of a war-funding request, the Senate voted 90 to 6 against appropriating $80 million to close Guantanamo. The administration was stunned.

The 9/11 trial. In his boldest move, Holder announced that Khalid Sheik Mohammed and his co-conspirators would be tried in a Manhattan federal courthouse less than a mile from Ground Zero. While the city initially welcomed this, the prosecution soon collapsed.

At the Justice Department, officials thought they had been sandbagged by inflated security estimates made by the New York Police Department, and exaggerated concerns about disruption to the life of the city. NYPD Commissioner Ray Kelly spoke about creating security rings around the courthouse at an annual cost of approximately $200 million.

Mayor Bloomberg was facing increased local opposition to the trial, but "the administration was silent and did nothing to help him."

Military commissions. In August 2010, the Defense Department began to advocate for a full resumption of military commissions. While Secretary of State Hillary Rodham Clinton argued that any military commissions should be accompanied by federal trials, Defense Secretary Robert M. Gates said he wanted to be able to lift the hold on commissions in 90 days.

The Ghailani trial. Ahmed Ghailani, a former high-value detainee at Guantanamo Bay, was charged with multiple counts of murder. His trial was in Manhattan, and might have served as a blueprint. But although Ghailani was given a life sentence for conspiracy to damage or destroy U.S. property, he was acquitted of 284 other counts, including all the murder charges. Critics seized on the fact that an an al-Qaeda terrorist almost got off.

The end of the road. In December, in the provisions of a major defense bill, Congress imposed the tightest restrictions yet on the handling of Guantanamo detainees. And while President Obama called the restrictions a “dangerous and unprecedented challenge” to the executive branch, he did not say he could lawfully ignore them.

As with any failure, the themes that emerge include a great deal of finger-pointing. Many believed that the White House never pressed hard enough on the goal. “They weren’t breathing down our necks pushing the vote or demanding unified action,” said one Democratic aide. There was a lack of leadership: “Everybody seemed to have a piece of it," said one Republican staffer, "but nobody was in charge of it.”

This article is from the archive of our partner The Wire.