The prospects for a truly liberal transatlantic international order that transcends the nation-state must be constructed with respect to the current challenges and context confronting nation states. Yet past attempts at federations can inform ongoing conversations about the prospects and challenges for such an order. Above all, past efforts to craft federations point to the importance that such arrangements are self-enforcing. This chapter considers the great experiments with federations in the political economic history of the United States. Through analysis of the Articles of Confederation, the Confederacy’s constitution, and the U.S. Constitution, it suggests that one of the most significant challenges for a polycentric arrangement that includes sovereign states is to ensure a reliable revenue mechanism to fund public goods beyond the level of sovereign states. To that end, this essay suggests that what is critical for consideration of a libertarian interstate federation is how to ensure a reliable source of revenue for such a confederation, as well as to ensure constraints on the supranational government that promises to improve prospects for global commerce and movement of people.