The North Carolina attorney general’s upcoming decision on whether to approve the proposed $1.5 billion sale of nonprofit Mission Health Systems to the for-profit behemoth HCA will have ramifications far beyond an 18-county, mostly rural mountainous region—certainly on the parameters of future hospital conversions, and possibly on the practice of rural philanthropy itself. As the largest per-capita infusion of philanthropic capital from a healthcare conversion in the nation, will the new Dogwood Health Trust be transformative, promoting real structural change in this piece of Appalachia, or will it perpetuate existing disparities and institutional practices?