Tracheal masses are rare in occurrence, but could lead to complications depending on the speed of growth, duration and degree of obstruction. Some of the complications are recurrent pneumonia and air trapping resulting in increased intrathoracic pressure. The latter phenomenon can result in obstruction of the venous return and pneumothorax. We are reporting a rare presentation of bilateral pneumothorax (presumed tensioned) in a young patient with a distal obstructive tracheal tumor. In the emergency department (ED) the patient was in respiratory distress and was found to have extensive subcutaneous emphysema of the neck, chest, and abdominal wall with hypotension. Respiratory failure from bilateral tension pneumothorax was suspected and the patient was intubated with simultaneous bilateral thoracostomy. These measures did not improve the patient's ventilation and oxygenation status. Further fiberoptic investigation revealed a distal tracheal obstructive mass. An emergency surgical intervention was required to remove the tumor. We recommend considering alternative pathologies, such as an obstructive tracheal tumor, in a patient with respiratory distress. They should especially be considered when oxygenation and ventilation are difficult, particularly when endotracheal intubation and/or tube thoracostomy fail to improve the symptoms. A high index of suspicion and a timely multidisciplinary team approach are essential when managing the life-threatening presentation of a patient with a distal tracheal tumor.