A 48-year-old man presented with gradually worsening dyspnea three days after testing positive for COVID-19. He was admitted to the intensive care unit on maximum high flow nasal cannula settings and subsequently intubated for hypoxic respiratory failure due to COVID-19 pneumonia. Two weeks into the patient's hospital course, he unexpectedly developed worsening hypotension with multiple vasopressor requirements. Labs revealed an unexpected hemoglobin drop from 12.5 to 7.9 g/dL. Chest radiograph showed near complete opacification of the right hemithorax concerning for hemothorax. This case presentation describes a rare phenomenon of spontaneous hemothorax in a patient with COVID-19.