We present a case of a 74-year-old male with a past medical history of polymyalgia rheumatica that presented as a transfer for evaluation of hematomas of the scrotum, left groin, back, and bilateral thighs. Further questioning revealed hematuria and bleeding gums for the past month. The patient complained of left thigh pain without recent fever, chills, chest pain, or shortness of breath. A physical exam showed hematomas of the left groin, scrotum, bilateral thighs, and back with an ecchymotic appearance. Initial pertinent laboratory workup showed decreased hemoglobin, leukocytosis, and elevated partial thromboplastin time (PTT). Therefore, a decision was made to obtain a CT angiogram of the abdomen and pelvis, which revealed retroperitoneal hematoma. Further diagnostic workup showed a coagulation factor VIII level of zero percent and mixing studies supporting the presence of an acquired factor VIII inhibitor. Therefore, the patient was treated with rituximab and recombinant factor VIIa, with an improvement of factor VIII levels to normal limits within a week.