Abstract: This essay looks at three issues concerning freedom in American history. First, it examines competing conceptions of freedom--positive/negative and individual/political-and considers whether the equal validity of these competing conceptions makes freedom such a malleable concept that it is vacuous. In other words, freedom apparently can be invoked with equal plausibility on either side of any significant political dispute. Second, the essay seeks to identify the circumstances or conditions under which particular freedoms prosper and expand. Third and finally, it considers the complex and sometimes paradoxical role that courts have played in the history of American freedom.