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Dr. Jonathan Silver is a visionary and dynamic thinker, a scholar, a master teacher, and an experienced and successful builder of college preparatory programs. He believes that our best learning is in doing and that our best teaching is in coaching. Jonathan began his professional life in schools as a middle school social studies and English teacher with Shady Side Academy, Pittsburgh’s premier independent school. After completing a masters degree in Educational Thought and Policy at the University of Rochester, he continued graduate work at Carnegie Mellon University, where he earned a second masters degree (History and Policy) and eventually earned his PhD degree in history. His major fields of study included the histories of education, childhood, youth, and adolescence. While working on his doctorate, Jonathan rejoined Shady Side Academy, serving as the school’s historian, as a dorm parent, and as Assistant to the President for Institutional Planning and Academic Resources. He also taught undergraduate courses in history at Carnegie Mellon University and graduate level courses in education at Duquesne University.

When the opportunity to help build a new high school program presented itself, Jonathan couldn’t resist. He became head of upper school and then assistant head of school with the upstart Emery/Weiner School in Houston, TX. Four years and three successful graduating classes later, Jonathan was recruited to take over the headship of The Village School in Houston. While with The Village School, Jonathan founded the new high school division, gained accreditation with the International Baccalaureate Organization (IBO), and established a very successful boarding program.

One of the key factors to Jonathan’s leadership success is that he earns the trust and respect of all of a school’s constituents. A former colleague commented that Jonathan has a wonderful track record of “igniting and empowering those with whom he worked (parents, students, teachers, and community leaders) to achieve great things.” Another colleague stated that Jonathan is “a champion for students and zealous for the success of others,” and his “approach is personal and fosters trust in a manner unlike any I’ve professionally known.” And, a parent commented: Jonathan “mixed an intellectual, seasoned approach to education with honest and heartfelt caring for students and their families.”

Jonathan was born and raised in Philadelphia and continues to root for his Philly sports teams. Even so, he much prefers to play than spectate, and will skip out on just about any kind of meeting if it means a chance to serve up tennis balls, shoot baskets, or swat softballs. He also enjoys spending time in the outdoors hiking trails and admiring Maui’s great vistas. Ultimately, however, what has brought Jonathan to Maui Preparatory Academy is the opportunity to work with a wonderfully optimistic and nurturing community committed to providing the best and most effective education we can for our students.