Thomas O. Pyle served in the top echelons of the Harvard Community Health Plan (HCHP) for nineteen years. In that time, HCHP became the largest health maintenance organization in New England, and its reputation for innovation and entrepreneurship rose to the top ranks of the industry. This interview explores Pyle’s background, his interpretation of HCHP’s evolution and eventual transition to a much different organization, and his recommendations for the future.