This chapter looks at Puerto Rico: 98, an art exhibit at Chicago's Puerto Rican Cultural Center and then at the Chicago Art Institute commemorating one hundred years of U.S. control over Puerto Rico and featuring visual meditations with respect to the Puerto Rican flag and the island's problematic nationhood. The exhibition was a manifesto in relation to the flag as well as flagism—banderismo. The three artists, Elizam Escobar, Ramón López, and Juan Sánchez, are independistas who have all led lives of political as well as artistic struggle. Their visions go far beyond any narrow nationalism or even the frustrated national aspirations of their colonized space of imagination and aspiration. From their barrio and prison worlds, these artists can see what amounts to a fascination of Puerto Ricans with their flag as a form of affirmation and resistance. However, they can also see this fascination as an obsession.