Posterior Mediastinal Hematomas (PMHs) secondary to a fall from standing height are uncommon, with only one previous case reported in the literature. We describe a case of a 78-year-old male with multiple medical comorbidities, who was transferred to Montreal General Hospital (MGH) with a posterior mediastinal hematoma (PMH) after sustaining a fall from standing height. On initial assessment, the patient was hemodynamically stable and complained of mild chest pain, dyspnea, fatigue, and diaphoresis. The patient's airway was secured via endotracheal intubation fearing impending respiratory compromise secondary to an enlarging PMH. The patient was admitted to ICU where over the next 3 days he was managed conservatively via careful monitoring of his hemodynamic and hematologic indices. Repeat CT scanning indicated reduction in size of the PMH. The patient was discharged on hospital day eight. This case describes the assessment, evaluation, and conservative management of PMH in a complicated patient receiving prior anticoagulation. A review of the literature regarding the epidemiology of PMH and the management of both unstable and stable PMHs is also presented.