A Fond Farewell to Maureen Sweeney After 39 Years of Service at The Windward School

Stephanie Huie

Director of Admissions and Assistant Head of School

For many parents and guardians of Windward students, Maureen A. Sweeney was the first person they encountered when they stepped through the doors of The Windward School. After 39 years of tireless dedication to thousands of students and their families, hundreds of teachers, dozens of trustees, and five heads of school, Maureen A. Sweeney, Director of Admissions and Assistant Head of School, retired on June 30. 

In 1979, Ms. Sweeney joined the Windward faculty as an assistant teacher, with a specialty in mathematics. She was quickly recognized as an asset to the School and was asked to take on roles of increasing responsibility. Eventually, she became a group teacher and later, head of Windward’s Upper School. 

She was appointed Director of Admissions in 1993; her knowledge of Windward and its programs, and her innate charm and gift dealing with the public, made her the ideal choice for the new leadership position. Then in 1996, because she had been such an effective spokesman for Windward and had such a thorough understanding of its goals and programs, she was asked to accept the additional role of Assistant Head of School. For the past 22 years, she has served jointly as Director of Admissions and Assistant Head of School.  

Since 1979, Windward has undergone a period of growth and development that is truly unique and unprecedented. The student body has increased by 1200%, the original building has been modernized and expanded, and the Westchester Middle School and the Manhattan campus have been established. Most important of all, Windward has built a language-based instructional program that has given it international renown for its success in educating learning disabled students. It is no coincidence that Ms. Sweeney has been at Windward during the time that these changes were taking place. In fact, she was instrumental in bringing them about. 

Dr. John J. Russell, Head of School, congratulated Ms. Sweeney on her retirement saying, “I would like to thank Maureen for her 39 years of devoted service to The Windward School community. Her intellectual curiosity, deep ethical grounding, tireless optimism, kindness, insane energy level, and sense of fun are characteristics which are at the heart of what Maureen Sweeney has meant to Windward. She has been unwavering in her dedication to preserving the traditions and values that have defined Windward throughout its 92-year history. She has exhibited warmth, kindness, and accessibility to our students and to the entire Windward community. Her ability to address complex issues with wisdom and clarity has been a constant strength of her leadership.” 

When reflecting upon her years as a colleague of Ms. Sweeney, former Head of School Dr. Judith C. Hochman, shared a few phrases that immediately came to mind: a legend in her own time, a force of nature, national treasure, and a fashion icon! "We shared an office for a year, a very small office. I had a front center seat to listen to Maureen, as Director of Admissions, taking and making countless phone calls to parent applicants, alumni students, and colleagues. I was in awe of her patience, on target questions and responses, and invariable kindness. She cares. She related to every parent and felt so deeply to every child who struggled. And somehow she's invariably upbeat and encouraging. We've been through a lot together as colleagues and friends, professionally and personally. Maureen is a brilliant educator, a valued colleague, a treasured and beloved friend. There's no one like Maureen Sweeney." 

Ms. Sweeney’s impact on the lives of Windward students and families is immeasurable. The entire Windward community is grateful for the wisdom and expertise Ms. Sweeney has imparted to everyone.