CBS News national security correspondent David Martin has exclusively learned that the president-elect's transition team has already asked the Pentagon what it would take to move the prisoners at Guantanamo to the Navy base at Charleston, South Carolina.
It's a clear sign that the new president intends to make good on one of his most emphatic campaign promises.
One high profile terrorist, Jose Padilla, was held at the Charleston brig before facing trial. But major construction and extraordinary security would be required to house all 250 Guantanamo inmates there. Other military bases, including Camp Pendleton, California are also being considered.
"The real question is what is our detainee policy in the war on terrorism and that's a question that is, you know, is going to be very wrenching," Wittes said.
Would prisoners held in the U.S. be tried by military commissions as they would at Guantanamo or by civilian courts? The waterboarding of 9/11 mastermind Khalid Sheik Mohmmed could jeopardize even that case in a civilian court, warns former federal prosecutor David Laufman.
"Everything that comes out of a detainee's mouth afterward is likely to be tainted," Laufman said.
More than 100 of the inmates are considered too dangerous to release but not guilty enough to prosecute because the evidence against them can not be used in court. Would an Obama administration hold those prisoners without trial?
"There is going to be a sobering moment when they get into office and they actually look at these files," Wittes said.
The real question facing Obama: Will he change the rules under which captured terrorists are held, or just their address?