“The oldest colony in the world.” That was the name José Trías Monge ’44 gave to his home, the Commonwealth of Puerto Rico, where he served as attorney general and chief justice. As the moniker suggests, the relationship between Puerto Rico and the United States—a democracy founded on the principle of self-determination—has always been complex, and throughout that history, Harvard Law School has played a significant supporting role. At the outset, the intellectual framework for the Insular Cases, which held that constitutional rights need not follow the flag, was crafted by Harvard scholars in the pages of the Harvard Law Review. Decades later, the school’s first Latino alumnus, Pedro Albizu Campos ’21, became the leader of the Puerto Rican Nationalist Party and led the fight for Puerto Rican independence. Trías Monge himself subsequently helped to draft the constitution that first established the commonwealth and that sought to redefine its relationship to the United States. Finally, that constitution’s legal status was just recently addressed by the U.S. Supreme Court for the very first time, in a case argued by two opposing Harvard Law School alumni that yielded opposing opinions authored by two additional alumni—one a former HLS dean, the other a former HLS professor. And yet today, the status of the relationship between Puerto Rico and the United States is perhaps as unsettled as it was in 1898. This panel of engaged alumni and experts, moderated by Assistant Professor Andrew Crespo ’08, looks back on this history and forward to examine the future of the relationship between one of the world’s leading democracies and its oldest colony.