Sir William Osler's great work and achievements are extensively documented. Less well known is his prolonged battle with postinfluenza pneumonia, lung abscess and pleural infection that eventually led to his demise. At the age of 70, he was a victim of the global Spanish influenza epidemic, and subsequently developed pneumonia. In the era before antibiotics, he received supportive care and opium for symptom control. The infection extended to the pleura and he required repeated thoracentesis which failed to halt his deterioration. He proceeded to open surgical drainage involving rib resection. Unfortunately, he died shortly after the operation from massive pleuropulmonary haemorrhage. In this article, we review the events leading up to Osler's death and contrast his care 100 years ago with contemporary state-of-the-art management in pleural infection.