After more than 60 years of military occupation, 30 of these under violent military practices, a social movement forced the U.S. Navy from the island of Vieques. This victory would not have been possible without the highly effective organization of civil disobedience carried out on the island. But the sum total of the actions that eventually forced out the U.S. Navy, neither happened exclusively within the boundaries of Vieques, nor was carried out by Viequense residents alone. In this article we want to suggest that this amazing victory—a testament of people’s will in the face of globalization—is also a border- crossing tale. Drawing from interviews with key activists currently based in Puerto Rico and New York, this article will explore the myriad routes of connections enacted, maintained and negotiated within and beyond territorial and ethnic boundaries. It will particularly look at how various activists conjured networks of solidarity, kinship, political affiliation, and friendship, among others, in their quest to liberate the island from the U.S. military occupation. Under the backdrop of Obama’s post-racial discourse, this paper illustrates how the Vieques movement circumvented the politics of Empire through creative maneuvers and negotiations.