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Recent scholarship on the Insular Cases has overlooked the consequences of these rulings for veterans of the American Armed Forces. Despite the fact that more than half a million nationals of the Philippine Commonwealth fought heroically under U.S command during World War II, Congress declared in 1946 that the vast majority would be ineligible for U.S. veterans’ benefits. Drawing on new archival research, this paper examines the contested politics of providing medical and pension benefits for members of the colonial Philippine Scouts and the Philippine Commonwealth Army. As the Trump Administration’s August 2019 decision to end special immigration privileges for Filipino veterans demonstrates, the racist legacies of empire and colonial inequality continue to influence public policy in powerful ways.