Many aspects of the relationship between the United States and its territories are inherently undemocratic. This Essay draws attention to one: the continued and systematic discrimination against United States territories in the appointment of judges to the federal courts of appeals. This failure not only contributes to the well-known diversity crisis within the federal judiciary but also to the stagnation in the development of the law of the territories as well as the persistent second-class treatment of the territories and their people under the United States Constitution as interpreted by the federal courts. Unlike larger and more difficult issues such as voting rights, territorial representation on the federal courts of appeals could be achieved through a simple amendment to 28 U.S.C. § 44(c) or by the president exercising his discretion to reject the unofficial custom of filling vacant circuit court judgeships with judges who hail from the same state as their prior occupants.