Venous aneurysms are rare and have a prevalence of 0.1 to 0.2% in the reported series. Typically, patients do not present any symptoms, but are prone to develop deep venous thrombosis (DVT) and the most feared complication, pulmonary embolism (PE). We present the case of a previously healthy 36-year-old man who presented at the emergency department with tachycardia, dyspnea, and pleuritic pain. A thoracic computed tomography angiography (CTA) confirmed the diagnosis of acute pulmonary embolism. He was treated with systemic thrombolysis and anticoagulation. In the further workup of the cause of the embolism, computed tomography revealed a fusiform dilation of the left popliteal vein measuring 3 by 3 centimeters (cm) with an incomplete filling defect because of thrombus presence. The patient underwent open surgical repair. At one month follow-up, he was asymptomatic, and an ultrasound revealed complete patency of the popliteal vein without dilatation or thrombus.