Faculty & Staff

Craig Osborne

Member Information

Department(s):	Administration Lower School Middle School Social Studies Upper School
Position:	Interim Dean of Middle and Upper School Students; Middle School Social Studies Faculty

Other Information

Biography
Education M.B.A Business Administration; University of Iowa M.S. National Security Strategy; National War College M.S. Military Theater Operations; U.S. Army Command and General Staff College M.S. Adult, Occupational, and Continuing Education; Kansas State University B.S. History; Illinois State University As the Interim Dean of Students at Wakefield School, Craig works closely with students, faculty, and families to cultivate a respectful, accountable, and growth-oriented school culture. In addition to his leadership role, he teaches Post-Classical World History to Middle School students and serves as an advisor to sixth-grade boys, emphasizing character development in alignment with Wakefield’s mission. Before joining Wakefield full-time, Craig spent over 2 years as a substitute teacher across both the Middle and Upper Schools, building strong relationships and developing an understanding of the school community. His professional background includes more than three decades of leadership in the United States Army, where he retired as a Colonel, followed by senior leadership roles in higher education at the National Defense University, Johns Hopkins University’s School of Advanced International Studies (SAIS), and The Catholic University of America’s Columbus School of Law. Most recently, he worked for Major League Baseball and the USL Championship League, gaining firsthand experience in high-performance team environments. Craig is excited to be part of the Wakefield community and was drawn to its strong culture of trust, respect, and authentic relationships, where students are both supported and challenged to grow. He looks forward to contributing to a community that values not only academic excellence but also the development of thoughtful, ethical, and engaged young people.

Biography

Education

M.B.A Business Administration; University of Iowa
M.S. National Security Strategy; National War College
M.S. Military Theater Operations; U.S. Army Command and General Staff College
M.S. Adult, Occupational, and Continuing Education; Kansas State University
B.S. History; Illinois State University

As the Interim Dean of Students at Wakefield School, Craig works closely with students, faculty, and families to cultivate a respectful, accountable, and growth-oriented school culture. In addition to his leadership role, he teaches Post-Classical World History to Middle School students and serves as an advisor to sixth-grade boys, emphasizing character development in alignment with Wakefield’s mission. Before joining Wakefield full-time, Craig spent over 2 years as a substitute teacher across both the Middle and Upper Schools, building strong relationships and developing an understanding of the school community.

His professional background includes more than three decades of leadership in the United States Army, where he retired as a Colonel, followed by senior leadership roles in higher education at the National Defense University, Johns Hopkins University’s School of Advanced International Studies (SAIS), and The Catholic University of America’s Columbus School of Law. Most recently, he worked for Major League Baseball and the USL Championship League, gaining firsthand experience in high-performance team environments.

Craig is excited to be part of the Wakefield community and was drawn to its strong culture of trust, respect, and authentic relationships, where students are both supported and challenged to grow. He looks forward to contributing to a community that values not only academic excellence but also the development of thoughtful, ethical, and engaged young people.

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