We report a longitudinal case of an obese subject presenting at age two (BMI percentile > 99) with symptoms of OSA. Polysomnogram revealed severe OSA (AHI 37.1/hour) with abnormal oxygenation and ventilation. Despite extensive desensitization to PAP, the subject was intolerant to PAP. A tracheostomy was placed due to a failed PAP attempt. Although some children treated with tracheostomy for OSA have medical complexities, this child had no underlying neurologic or craniofacial syndromes. Tracheal de-cannulation occurred following a systematic approach including multiple polysomnograms and PAP desensitization. However, due to inability to resolve OSA with PAP and pressure intolerance, reinsertion of tracheostomy was considered. A second tracheostomy was avoided at age 17 (BMI percentile > 99) by utilizing a commercially available positional device in conjunction with PAP (AHI 3.4/hour, normal oxygenation and ventilation). Although the utilization of a PAP in conjunction with PAP proved effective in this case, there is limited literature documenting concurrent use, and no current literature describes this practice in children. Further research is needed to determine if the combination of a positional device along with PAP is an effective treatment option in pediatric patients with difficult to treat OSA.