Taking medications are complex symbolic acts, infused with diverse meanings regarding body and identity. This paper focuses on the meanings of medications for older Puerto Ricans living on the United States mainland, a population experiencing stark health disparities. We aim to gain an understanding of the way multiple cultural and personal meanings of medications are related to and integrated in identity, and to understand how they are situated within Puerto Rican culture, history and situation on the US mainland. Data is drawn from thirty qualitative interviews, transcribed and translated, with older Puerto Ricans living on mainland United States. Thematic Analysis indicated four prevalent themes: Embodiment of medication use; Medications redefining self through the fabric of daily life; Healthcare experience defined through medication; and Medicine dividing the island and the mainland. While identity is impacted by experience of chronic illness, the experience of medication prescription and consumption is further related to the construction of the sense of self in distinct ways. For these individuals, medication use captures the dilemma of immigration. While cultural belonging and well-being remains on the island of Puerto Rico, the mainland hosts both easier access to and excess reliance on medication.