Russ Gregg (B.A., Global Studies, University of Wisconsin-Madison) is co-founder and has served as Head of School since Hope Academy’s founding in 2000. He has been a resident of the Phillips neighborhood since 1994. In 1999, he was an administrator at a Christian School in Edina, and quit his job to help lay the groundwork for a Christian school for his urban neighbors. Russ and his wife Phyllis, who teaches at Hope Academy, live four blocks away from the school. They have three grown children. Russ serves on the Board of Directors of the Society for Classical Learning.
Roosevelt has a doctorate in Educational Leadership, a master's degree in Educational Leadership, a master's degree in Elementary Education, and a bachelor's degree in psychology. He comes to Harbor Christian Academy from Spring Independent School District, where he served as principal his final five years and assistant principal for four years prior. He also has six years of experience as a classroom teacher. Before beginning his career in education, Roosevelt served with the United States Marine Corps. A few highlights of his 23-year tour as a Marine include Instructor at the Drill Instructor School in San Diego, CA, Administrator at the Staff Noncommissioned Officer Academy in Okinawa, Japan, and also in Beaufort, SC, as the director of the Lifelong Learning Center. He is husband to Octavia and the father of four adult children.