Past Assistant Principals of the Year Assistant Principal of the Year Winner(s) 2025 LaFaye Howard, Winston Churchill High School, Montgomery County Anna Ory, Marley Middle School, Anne Arundel County 2024 Sheri Murphy, Frederick High School, Frederick, MD 2023 Ricardo Hernandez, Paint Branch High School, Burtonsville, MD 2022 Dr. Kimberly Culbertson, Towson High School, Baltimore County 2021 Raymona Reid, Oakland Mills High School, Howard County Deana Giannelli, Perry Hall Middle School, Baltimore County 2020 Catherine Sutton, Calvert High School, Calvert County 2019 John Seibel, Hammond High School, Howard County 2018 Debra O'Byrne, Glenwood Middle School, Howard County 2017 Rob Willoughby, Caroline County High School, Caroline County 2016 Ashanti Foster, Oxen Hill Middle School, Prince Georges County 2015 Dyan Harrison, Gaithersburg High School, Montgomery County 2014 Jared Wastler, Liberty High School - Carroll County 2013 Everett M. Davis, Montgomery Village Middle School - Montgomery County 2012 Tammy L. Goldeisen, Folly Quarter Middle School - Howard County 2011 Richard Conley, Henry Lackey High School - Charles County 2010 William Eckles, Carrol County Career and Technology Center - Carroll County 2009 Melissa Shindel, NASSP/Virco National Assistant Principal of the Year, Patuxent Valley Middle School - Howard County 2008 Brenda Wilks, Gaithersburg High School - Montgomery County 2007 Christopher S. Berry, James "Eubie" Blake High School - Montgomery County Jennifer Clements, Mount Hebron High School - Howard County 2006 Robert A. Motley, Centennial High School - Howard County 2005 Lori L. Batts, Mardela Middle and High School - Wicomico County 2004 Patricia A. Adkins, James M. Bennett High School - Wicomico County 2003 Ed Evans, Long Reach High School - Howard County 2002 Charles Crue, Edgewood High School - Harford County 1998 Addie Kaufman, Atholton High School - Howard County
