Annually since 1986, the Yonkers Board of Education, in collaboration with the Rotary Club of Yonkers – East Yonkers awards the Leadership in Education, also known as the Administrator of the Year, which is presented to an administrator who personifies the spirit, dedication and accomplishments of an outstanding instructional leader. “Dynamic educational leaders understand and act on what is necessary to produce positive academic, behavioral and social-emotional outcomes for their students as well as supporting staff to achieve that common goal.” Executive Director Dr. Stephanie McCaskill personifies these qualities, applauds Dr. Edwin M. Quezada, Superintendent of Yonkers Public Schools, “Dr. McCaskill instantly embraced the complex work of our Special Education and Pupil Support Services Department with almost 6,000 students and 380 teachers, 100 Teaching Assistants and 300 school aides. With every task she has been asked to oversee, Dr. McCaskill accomplishes it with the upmost professionalism, fidelity and clear commitment to do whatever it takes to meet the needs of the child.”

Dr. Stephanie McCaskill received a Bachelor of Arts in Communications Arts & Science from CUNY Queens College and a Master of Science in Education from the College of New Rochelle. In May 2023, she received a Doctorate in Leadership and Innovation from the New York University’s Steinhardt School of Culture, Education and Human Development, where her professors asked her to participate in a university-sponsored global forum of educational leaders in Abu Dhabi. 

In 2018, Dr. McCaskill began her career in the Yonkers Public Schools as the Executive Director of Special Education and Pupil Support Services Department bringing her broad expertise as a related service provider, school principal and a New York City School Special Education Network Leader. 

When asked what she likes most about her job, Executive Director Dr. McCaskill wrote, “The most rewarding part of my job is to visit classrooms and see students learn. I believe that ALL students can learn, and this is evident in my school visits. Also, working with parents to understand how their child learns is a critical function of my job. The connection between school and home is a fundamental component of educating the whole child.”

Dr. McCaskill’s own words were echoed by the nominators for this award, the entire Special Education and Pupil Support Services Department administrative team: Assistant Superintendent Dr. Luis Rodriguez, and Directors Deborah Mason, Dr. Caroline Letendre, Dr. Rod Williams-Rodriguez and Jak Curanovic.

Dr. McCaskill, “has demonstrated an unwavering commitment to quality education, through the realization of her comprehensive programmatic vision. This is reflected in her work in multiple settings, including her observational work of Special Education teachers and support staff, and the resultant professional development activities for schools, that she conducts. Dr. McCaskill coordinates the implementation and documentation of the District’s response to NYSED Compliance Reviews and the Department’s Special Education District Plan. 

Working with teachers and school aides, Dr. McCaskill provides “targeted” training, using measures that improve teacher practice and promote student achievement for our students with disabilities. Dr. McCaskill also functions as chief operating officer for Central Office Special Education Department operations, and supports to school level Pupil Support Teams (PST). In this way, Dr. McCaskill ensures tiered interventions are in place promoting student access to curricula in general education settings, obviating the need for referral for more restrictive programming.

An ardent advocate for quality education, Dr. McCaskill conducts professional development in schools on topics ranging from: “Providing Tier One MTSS Supports” and “Understanding Learning Disabilities,” to demystifying Autism, for both school-based personnel and for parents. She serves as the District Liaison to Yonkers Special Education Parent Teachers Association (YSEPTA).

Academic achievement and socio-emotional growth for students with disabilities are very high on Dr. McCaskill’s professional priorities list. She observes, provides feedback and coaches both special education and general education teachers at various District schools. Her involvement in such field activities has resulted in requests from additional school leaders for similar support. Dr. McCaskill conducts structured observations of specific students at the request of either parents and/or administrators, and functioned as a resource to them in designing responsive Behavior Intervention and other support plans.”

Dr. Stephanie McCaskill has two amazing sons, Sean and Charles. In addition, her extended family, which includes siblings, a host of nieces, nephews, and grandnieces/nephews is a source of great love and immense joy.

The Leadership in Education Award Program, inaugurated in 1986 by the Rotary Club in association with the Yonkers Board of Education, recognizes the significant role of school leadership in achieving student success.