The next steps are likely to depend on how many prisoners are among those the administration decides cannot be tried or sent home, said Vijay Padmanabhan, a visiting assistant professor at Yeshiva University's Cardozo School of Law in New York who until recently handled detainee issues at the State Department.
The pressure for new legislation could be increased if officials find a larger number of prisoners who can neither stand trial nor go home. Possible legislation includes indefinite detention, a new national security court and blocking detainees from seeking asylum.
The option of releasing prisoners to their home countries could pose difficulties for the Obama administration. Padmanabhan noted that when a former Guantanamo detainee set off a bomb in Iraq this year, it received relatively little attention.
"But if the same thing happened with the Obama administration, it would not be a small news story," Padmanabhan said, adding opponents would accuse the new president of releasing dangerous terrorists. "In that sense, the politics are harder for Obama than they were for Bush."
The difficulty of holding trials is highlighted by the case of self-proclaimed Sept. 11 plotter Khalid Shaikh Mohammed, who was subjected to the simulated drowning technique known as waterboarding while held by U.S. officials. The ACLU argues that if all of the evidence against a prisoner is tainted by torture, the detainee should be let go.
Nonetheless, Jaffer of the ACLU thinks Mohammed can still be tried because of an earlier indictment in the 1995 plot in the Philippines to blow up airliners headed for the U.S. The evidence used to indict him could probably be used to try him, Jaffer said.
But Guter, the former Obama campaign advisor, is skeptical that a Mohammed prosecution is possible and thinks allegations of torture would entangle any trial.
"Most of these problems we made ourselves. We could have had enough to convict," he said. "We didn't trust our own institutions that had served us all these years. We didn't trust in our federal courts, we didn't trust in our Constitution."
One Obama advisor, who spoke on condition of anonymity when discussing undecided issues, acknowledged the difficulty of the task ahead.
"There will be complicated choices to be made about individual detainees," the advisor said. "We all know what the options are. There is nothing new under the sun. They are all going to be looked at."
And it is clear that solutions will take time.
"Guantanamo will be closed, but these people will be transferred somewhere, and some of them will need to be held for some time," said Deborah Pearlstein, a national security law scholar at Princeton University. "It doesn't make sense to say this will be resolved on Jan. 20."
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