When Virchow’s triad is disrupted, a deep vein thrombosis (DVT) can often occur and progress into a pulmonary embolism, and in rare cases, a saddle pulmonary embolism. This 28-year-old male patient showed up at the emergency department (ED) with shortness of breath, chest palpitations, and right calf pain. Additional imaging showed a massive saddle pulmonary embolism, and he was taken to immediate right femoral catheterization for thrombectomy. Though this patient presents with no known risk factors in his history or workup, he stretches the predefined boundaries with his cavalier presentation.