Puerto Rico's healthcare system exists in a state of crisis, shaped by decades of economic decline, colonial neglect, and systemic underfunding. This paper examines structural inequities, such as capped Medicaid funding, that have contributed to a fragile system unable to meet Puerto Ricans’ needs even before Hurricane Maria, one of the deadliest hurricanes in U.S. history, devastated the island. Survivor accounts and health data reveal compounding failures, including infrastructure collapse, where complete power/water loss led to lethal treatment delays; mental health deterioration, with suicide rates skyrocketing post-disaster; workforce shortages, as low wages, unbearable working conditions, and insurer corruption drive medical professionals to the mainland. Without Medicare/Medicaid parity, infrastructure investment, appropriate disaster planning, and medical workforce support, recovery remains impossible—raising worries that the next disaster will yield even deadlier consequences.