Elderly patients are often considered poor surgical candidates for intra-thoracic operations due to the number of comorbidities, increased risks associated with general anesthesia, decreased cardiopulmonary reserve, and overall increased frailty. In addition, coronavirus disease 2019 (COVID-19) is a critical psychosocial factor that, through secondary effects, can prevent patients from receiving optimal care. Patients are reduced to having limited contact with family, often a vital support system, which can contribute to feelings of hopelessness, loneliness, and depression. We report the case of a 95-year-old female who presented to the emergency department with increasing supplemental oxygen requirements two weeks after a ground-level fall. She was found to have multiple rib fractures and a left-sided hemothorax. Initial management included aggressive respiratory therapy, multiple pigtail chest tubes, and thrombolytics; however, these measures failed to drain the intrathoracic hematoma. Her care was complicated by the psychosocial and isolation factors of COVID-19 which led to the patient exhibiting symptoms of hopelessness, grief, lack of appetite, and loneliness. As conservative management did not improve her clinical care the patient required a video-assisted thoracoscopic surgery (VATS) to manage the retained hemothorax and facilitate re-expansion of her atelectatic lung. Once the patient was removed from COVID-19 precautions, she was taken to surgery and postoperatively the patient reported minimal pain, participated more in physical therapy, and increased her oral intake. In this unique case, a 95-year-old patient with a hemothorax that was successfully treated with a VATS had her clinical care complicated by the psychosocial implications of COVID-19.