Madison Reporter

MCPASD has announced the appointment of Barry Holloway and Bill Richardson as associate principals at Middleton High School, starting July 1, 2025. The decision follows a selection process described as "comprehensive and thoughtful" by current associate principal Bobbie Reinhart, who will become the principal of Middleton High School on the same date.

Reinhart stated, “After a comprehensive and thoughtful selection process, Bill and Barry rose to the top of a highly competitive candidate pool. Both bring with them strong instructional backgrounds and a deep commitment to supporting staff and students. We are confident they will be valuable additions to our leadership team, and we are thrilled to welcome them to MCPASD.”

The vacancies arose due to Carmen Klassy moving to Glacier Creek Middle School as principal and Jamie Sims accepting a principal position at Milwaukee Academy of Science.

Richardson comes from East High School in Madison where he served as an associate principal. His background includes teaching business at Vel Phillips Memorial High School and coaching boys track and field. He holds degrees from Edgewood College and the University of Missouri, with ongoing doctoral studies in educational leadership at Edgewood College.

Richardson emphasized his focus on equity: “I want to focus on fostering equity and closing achievement gaps, particularly for students from traditionally marginalized groups, while focusing on having all students achieve college, career, and community readiness. Every student deserves access to high-quality educational opportunities that foster academic excellence and build a strong sense of identity and belonging.”

Holloway currently works as Dean of Students at Janesville Craig High School. His experience includes teaching English at Hamilton Sussex High School and Wauwatosa East High School. He earned his degrees from the University of Wisconsin-Whitewater and the University of Wisconsin-Madison; he is pursuing a doctorate in K-12 leadership at the latter institution.

Holloway expressed his vision for school leadership: “I want to lead a school where I would love to work as a teacher and where I know my children would get a complete and quality education. I want to lead a school where people like my wife – who have no experience in education – would still feel comfortable communicating with the school's staff, connecting with the school's culture, and participating in the opportunities they'd be given to engage and interact as a member of the school community.”

MCPASD anticipates their contributions not only within Middleton High School but also throughout the broader community.