Schools
Assistant Principal Of DEI Promoted To Principal Of Highland Park High School
Longtime HPHS teacher, counselor and administrator Holly Fleischer succeeds HPHS Principal Debby Finn, who retires at the end of the year.

HIGHLAND PARK, IL — School board members in Township High School District 113 this week announced a successor for Highland Park High School's retiring principal.
HPHS Assistant Principal for Diversity, Equity and Inclusion Holly Fleischer will follow in the footsteps of Debby Finn, who is set to retire after a 25 years working for her hometown district, the last six of which she has spent in the HPHS principal's office.
Fleischer was promoted to principal for a three-year team, beginning in July, on the recommendation of incoming Superintendent Chala Holland, who the board picked in February to take over from Bruce Law.
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Holland said in a statement that she worked with the consultants hired by the district last year and other groups of people to identify the ideal candidate based on a profile created by members of the school community.
"At each step, I continuously assessed the feedback about each candidate against that profile. The decision became clearer in revealing the leader who can effectively lead HPHS into a new phase of excellence for each student," Holland said.
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"I am honored that Holly has agreed to serve in this role," she added. "She is relentless in her drive as an educator, she is a mindful listener and reflective leader. Holly is action-oriented, using quantitative and qualitative data to inform her insights. Her commitment in service to students is inspiring.”
Before becoming an assistant principal, Fleischer was the district's director of multi-tiered system of supports. That job required her to come up with ways of monitoring and analyzing student progress and "adjusting interventions" to help students access the curriculum, according to district representatives.
Fleischer started her HPHS career with nine years of teaching English to high schoolers before she got a master's degree in counseling and spent a decade in various counseling roles, where she helped with college planning, crisis and mental health interventions, risk assessments and other efforts to help students and their families.
"Highland Park High School has been my home for the past 21 years and I am beyond thrilled to be named the next Principal of a place I hold so dear to my heart,” Fleischer said in a statement.
“I have a keen awareness of our many assets and the various ways we need to improve to serve our community better. I am excited and humbled by the opportunity to contribute my skills and knowledge to this role in service of supporting and empowering all HPHS students and staff in our House on Vine," said Fleischer, a Deerfield resident.
"Together, we will work to build pathways that enable all students to reach their limitless potential, without sacrificing their authentic selves.”
Finn took over as HPHS principal shortly after the board paid $300,000 to oust one of its former superintendents following the resignation of the previous principal amid a criminal investigation.
The retiring principal remains a defendant in a lawsuit filed by a former assistant principal includes several allegations involving the circumstances surrounding the resignation of Finn's predecessor Tom Koulentes. Following a district investigation the prior year that determined he had intentionally falsified a teacher's walk-through observation, he was given a five-day unpaid suspension and final warning.
Documents filed as exhibits in the case show attorneys for the district contacted then-Lake County State's Attorney Mike Nerheim to report concerns that Koulentes and two of his assistant principals, Casey Wright and Eileen McMahon, may have committed several crimes by destroying thousands of physical records and trying to delete tens of thousands of emails without authorization before leaving the district in 2017.
After Finn's appointment as interim HPHS principal, the district's general counsel told prosecutors the board was not interested in pressing charges or "further criminal investigation," though the whistleblower suit alleges a conflict of interest and points out that lawyer and Finn both had personal and professional ties with Koulentes.
Final discovery in the case is scheduled to be complete by the end of this month. According to a joint report from attorneys for the whistleblower HPHS teacher, the district and Finn, all sides "believe that depositions will assist them in evaluating the case and will revisit settlement as discovery is completed."
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