Chest pain is one of the major causes of emergency room visits. Here, we present the case of a patient with chest pain who developed recurrent pneumothorax and Takotsubo cardiomyopathy (TC). An 80-year-old man, receiving supplemental oxygen for chronic obstructive pulmonary disease (COPD), presented to the emergency room with chest pain and dyspnea. On examination, his chest pain was initially assessed to be secondary to recurrent pneumothorax. However, on further evaluation, an electrocardiogram (ECG) showed ST-segment elevation along with elevated troponin levels. Ultimately, he was diagnosed with TC. ECG, if indicated by echocardiography, should be considered to detect concomitant heart disease when dealing with pneumothorax. TC should be recognized as a cardiac disease that can be caused by pneumothorax.