Musculoskeletal injuries are among the most common chief complaints in the geriatric population. Shoulder pain with associated deformity should be evaluated for possible joint dislocations, fractures, and musculotendinous tears. A comprehensive evaluation beginning with history and physical examination is important. Typical imaging utilized for the diagnosis of shoulder injuries includes plain radiography, ultrasound, and magnetic resonance imaging (MRI). We present a case of a 75-year-old male with massive rotator cuff tears and subsequent shoulder deformity. Management with non-surgical or surgical approaches should begin as soon as possible to delay the development of rotator cuff arthropathy.