There have been previous studies that suggested that patients with Parkinson’s disease are at an increased risk of thrombosis, but could Shy-Drager syndrome, which entails Parkinsonian features, be a risk factor for thrombosis also? Our patient is a 54-year-old male with Shy-Drager syndrome who presented to the emergency department with acute onset of pleuritic chest pain and shortness of breath. Initial work-up showed normal electrocardiogram, negative troponins, normal complete blood count, and normal chemistry panel, but an elevated D-dimer. Computed tomography of the chest with intravenous contrast was performed which revealed a large saddle pulmonary embolus extending into the right and left pulmonary arteries. Interestingly, the patient remained hemodynamically stable throughout his stay in the hospital.