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Mr. Desi Stewart, Monticello Dean of Students

Meet Desi Stewart, CHHS Alumnus Class of 1997. Mr. Stewart currently serves as the Dean of Students at Monticello Middle School, coaches track and field at Cleveland Heights High School, and also works for the high school athletic department.


In 2022, Mr. Stewart was named educator of the year by the CHUH School District for his work in a dual role as teacher and Dean of Students. This year his focus is on his role as Dean in which he provides student and staff support, assists administrators with student supervision, discipline, and guidance, provides instructional leadership, and assists with student activities. At Monticello Mr. Stewart speaks with students about small issues like opening a locker to large issues like conflict resolution. He greets students as they enter the building and does daily classroom checks because his goal is to speak to every student each day. “I want the students to feel safe, supported, heard, and noticed.”


In addition, Mr. Stewart is currently working with Pastor Kevin Mc Intyre of Church on the Heights to co-facilitate the Mighty Males of Monticello program. This program, which has grown already from 15 to 30 participants, meets bi-weekly to teach leadership and communication skills. Mr. Stewart is hoping that what is being taught in the program will boost students’ academic and social confidence and improve their attendance and grades.


Mr. Stewart has been an educator for 19 years. He has worked for the Euclid, Maple Heights, and Richmond Heights school districts as a teacher and as director of athletics. Mr. Stewart says he loves coming to work every day and credits his ability to make great things happen directly to the help and support he receives from Dr. Jeff Johnston, Monticello Principal, Ms. Brigette Pronty, Monticello Assistant Prinicipal, and other support staff members.


When he is not at work, Mr. Stewart is a dedicated friend and family man. It is important to him to be a good husband, father, son, brother, and uncle. He said, “There is nothing that I enjoy more than spending time with my family.”

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