The Insular Cases, a relic of imperial-era judicial reasoning, have long dictated the political and constitutional status of U.S. territories. In United States v. Vaello-Madeo, Justice Neil Gorsuch’s concurring opinion signaled a critical moment for reevaluating these precedents. This Note examines the enduring consequences of the Insular Cases, focusing on the Pacific Island Territory of Guam as a case study. Specifically, it explores how Guam’s political subordination—rooted in the judicial distinction between incorporated and unincorporated territories—has led to disparities in federal Medicaid funding. By analyzing the relationship between territorial representation in Congress and the structural inequities in health care funding, this Note argues that the constitutional instability caused by the Insular Cases presents a ripe opportunity for legal challenge. Justice Gorsuch’s opinion opens a path for reconsidering the Insular Cases, with federal Medicaid funding serving as a compelling vehicle for addressing the broader constitutional and democratic deficiencies imposed on U.S. territories.