Chest drain placement is a standard procedure for treating pneumothorax and pleural effusions and has a low complication rate. It is a safe and efficient procedure if image guidance is used. If the anatomic orientation is hampered and neither air nor fluids can be initially aspirated, more complex imaging than a chest x-ray is indicated to avoid major complications. We report the case of an 88-year-old male patient suffering from chronic heart failure who was admitted to another hospital following acute cardiac decompensation. Because of dyspnea with voluminous bilateral effusions, an attempt was made to drain the left pleural cavity. A malposition of the chest drain was suspected because blood was initially draining from the catheter. The hemodynamically stable patient was referred to our university hospital, where computed tomography of the chest revealed the location of the intercostal drain. The drain had perforated the left ventricle, run through the mitral valve and exited the left atrium via a pulmonary vein, ending in the middle lobe. The patient was brought to the surgical theater, where cardiac surgeons performed a left anterolateral thoracotomy and extracted the drain successfully. Three days later, the patient was discharged from our hospital in a good general condition.