Venous aneurysms are extremely rare and can have devastating consequences such as pulmonary embolism and death. We are reporting a case in which a patient who had two episodes of pulmonary embolism was found on duplex ultrasound to have a popliteal venous aneurysm. The patient was managed with operative repair. In this report we will examine the prevalence, diagnostic considerations, and treatment options for this unusual and potentially lethal clinical condition.