This is a case of an 18-year-old male who presented with hip pain, shortness of breath, and respiratory failure and was found to have a large saddle pulmonary embolus involving the pulmonary artery bifurcation, which extended into the main right and left pulmonary arteries, as well as the lobar branches bilaterally. The patient was taken to the operating room for an emergent pulmonary embolectomy where a significant amount of tumor was removed through an incision in the main pulmonary artery with pathology consistent with metastatic chondrosarcoma.