Lipomas are the most common benign soft tissue tumor. Yet, strikingly simple tumors can become problematic when compounded by odd characteristics such as size and location. We report the case of a 53-year-old male who developed complete right lung collapse secondary to a large right-sided chest wall lipoma with accelerated growth in the past 6 months. Bronchoscopy revealed extrinsic compression of the right mainstem bronchus. Histopathology of the soft tissue mass was suggestive of a lipoma. The mass was not amenable to surgery due to a high risk of mortality from his underlying comorbidities. His hospital stay was complicated by progressive end-stage restrictive lung disease necessitating intubation and eventually a tracheostomy, recurrent pneumonias, multiorgan dysfunction, and his eventual demise. We highlight a rare presentation of an unchecked lipoma, which ultimately led to the death of our patient. Simple lipomas show insidious growth and can remain asymptomatic until they reach a large size. Chest wall tumors should be considered malignant until proven otherwise by excisional biopsy. This reiterates the need to treat all chest wall tumors with wide resection in order to provide the best chance for cure.