Diaphragmatic liver herniation is often associated with thoracoabdominal trauma. Spontaneous diaphragmatic rupture is a thoracoabdominal emergency and requires a high index of suspicion combined with high-resolution imaging studies for establishing an accurate and timely diagnosis. We present a case report of a patient who was admitted to the emergency department with severe substernal chest pain and shortness of breath who was diagnosed with spontaneous diaphragmatic rupture and caudate liver herniation. The caudate lobe was incarcerated, contributing to the patient's symptoms. A celiotomy was performed and the defect was repaired primarily.