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When the U.S. Supreme Court issued its first detainee decisions in 2004, many cheered the Court for serving as a check on the George W. Bush administration's unilateral detainee policies. A closer examination, however, reveals that the Bush administration was adept at retaining significant power over detainee matters in spite of the seemingly negative judicial decisions. This article explores four institutional and political factors that, individually and collectively, work to limit the Supreme Court's ability to serve as a significant check on presidential power in the area of detainee affairs in the war on terror. The article concludes that, even if the judiciary is inclined to be active in this area, these factors are likely to constrain any judicial attempts to significantly check presidential detention power in the war on terror.