A 46-year-old man with a history of alcohol use disorder, tobacco use, and chronic pancreatitis complicated by an untreated pseudocyst presented with two days of right lower extremity swelling and pain, shortness of breath, and pleuritic chest pain. A right lower extremity Doppler showed a saphenous vein thrombus, and CT angiography of the chest revealed multiple bilateral segmental pulmonary emboli with involvement of the right distal main pulmonary artery. The patient had no personal or family history of venous thromboembolism, and review of systems was not concerning for an underlying oncologic or active inflammatory process.