A watch tower is seen in the currently closed Camp X-Ray which was the first detention facility to hold 'enemy combatants' at the U.S. Naval Station on June 27, 2013 in Guantanamo Bay, Cuba.
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Obama’s incremental progress towards Guantanamo goals

For much of 2014, the progress of transferring prisoners from the detention facility at Guantanamo Bay was slow and frustrating. From January to October, just six detainees were transferred from the prison.
But in the year’s final two months, there was a flurry of activity, including an announcement a week ago of five more detainees being transferred to Kazakhstan.
Helene Cooper put the progress in context yesterday.
In a series of secret nighttime flights in the last two months, the Obama administration made more progress toward the president’s goal of emptying the military prison at Guantanamo Bay, Cuba, than it had since 2009. The accelerated pace came after an era of political infighting and long bureaucratic delays.
Now 127 prisoners remain at Guantanamo, down from 680 in 2003, and the Pentagon is ready to release two more groups of prisoners in the next two weeks; officials will not provide a specific number. President Obama’s goal in the last two years of his presidency is to deplete the Guantanamo prison to the point where it houses 60 to 80 people and keeping it open no longer makes economic sense.
Of the 127 remaining detainees, the NYT report noted that 59 of them are “low-level prisoners deemed eligible for release, many of them Taliban foot soldiers who were never charged with a crime.”
Obviously, the other 68 are going to be the toughest cases, but for the White House, that’s not really the point.

Rather, the question for Congress then becomes one of fiscal responsibility:  why should the United States continue to invest millions of dollars in a facility that houses just dozens of men – none of whom have super powers? How long can lawmakers reasonably expect to keep open a detention facility that does not further our national security interests, continues to be a blight on our reputation, and serves as a rallying cry for our enemies?

Looking ahead, Obama is likely to get increased cooperation from Ashton Carter, his Defense Secretary nominee, as compared to Chuck Hagel, who used his Pentagon post to slow-walk detainee transfers.

The administration, however, will not have the services of Clifford Sloan, the State Department envoy who’s focused specifically on transferring Guantanamo prisoners, and who recently announced his departure from the administration. If you missed it, Rachel’s recent segment on Sloan is worth your time.
The Rachel Maddow Show, 12/23/14, 9:22 PM ET

Unexpected departure for State Department's Guantanamo envoy

Rachel Maddow reports the surprising news that the Clifford Sloan, the State Department envoy whose job has been to arrange the transfer of prisoners from Guantanamo Bay, is leaving his position despite a recent spike in productivity.

Foreign Policy, Gitmo and Guantanamo

Obama's incremental progress towards Guantanamo goals