To address the risks associated with polypharmacy, health care providers are investigating the feasibility of deprescribing programs as part of routine medical care to reduce medication burden to older adults. As older adults are enrolled in these programs, they are confronted with two dominant and legitimate accounts of medications, labeled the medication paradox: medications keep you healthy but they might be making you sick. We investigated how the medication paradox operates in the lives of older adults. In-depth qualitative interviews were conducted and analyzed with older adults aged 70+ to identify the various paradoxes that seniors live through regarding their medications and the narratives that they engage to negotiate these contradictions. Older adults were found to have established interpretative repertoires to make sense of the incongruent narratives of the medication paradox. In this article, we demonstrate older adults’ efforts to carve out their unique place in the dichotomized institution of medicine.