MCPASD is proud to announce the appointment of two associate principals – Barry Holloway and Bill Richardson – at Middleton High School, effective July 1, 2025.
“After a comprehensive and thoughtful selection process, Bill and Barry rose to the top of a highly competitive candidate pool,” said current associate principal Bobbie Reinhart, who assumes his new role as principal of Middleton High School on July 1. “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 roles were open due to current Associate Principal Carmen Klassy assuming the principal role at Glacier Creek Middle School, effective July 1, as well as current Athletic Director Jamie Sims accepting the principal position at Milwaukee Academy of Science.
Richardson currently serves as an associate principal at East High School in Madison. He previously worked as a business teacher at Vel Phillips Memorial High School, where he also served as head coach of the boys track and field team.
Richardson earned his bachelor’s degree from Edgewood College and his master’s degree from the University of Missouri. He’s currently pursuing his doctorate in educational leadership from Edgewood College.
“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,” Richardson said. “Every student deserves access to high-quality educational opportunities that foster academic excellence and build a strong sense of identity and belonging.”
Holloway is currently a Dean of Students at Janesville Craig High School. He previously served as an English teacher at Hamilton Sussex High School. He also taught at Wauwatosa East High School.
Holloway earned his bachelor’s degree from the University of Wisconsin-Whitewater and his master’s degree from the University of Wisconsin-Madison. He’s currently pursuing his doctorate in K-12 leadership at the University of Wisconsin-Madison.
“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,” said Holloway. “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 welcomes Richardson and Holloway to the District and looks forward to their leadership at Middleton High School and in the larger community.