Leptospirosis is a rare zoonotic disease which occurs in people exposed to contaminated water or/and animal urine. We report two cases of moderate to severe leptospirosis. The first case was a healthy middle-aged biology professor who recently visited his family in Jamaica and presented with multi-organ failure. The second case was a 27-year-old police officer who was admitted for acute liver injury and thrombocytopenia after helping people evacuate during a flood/disaster situation.