The Insular Cases have, since 1901, granted the political branches significant flexibility in governing U.S. territories like American Samoa and Puerto Rico—flexibility enough, indeed, to ignore certain constitutional provisions that are not “fundamental” or which would be “impractical” to enforce in the territories. Long maligned as judicial ratification of empire, predicated on racist assumptions about territorial peoples and a constitutional theory alien to the United States, the Insular Cases had a curious renaissance in the late twentieth-century. As local territorial governments began to exercise greater self-rule, newly-enacted local laws in the territories began to pose constitutional issues, but courts generally acquiesced in these constitutional deviations. This Note argues that this accommodationist turn in Insular doctrine complicates the legacy of the cases—that their use to enable local peoples to govern themselves as they desire, and to protect their cultures, means the Insular doctrine is not merely defensible but perhaps even necessary, and finds support in arguments from political theory. Moreover, the Note contends, such constitutional accommodation has a long pedigree in the American constitutional system.