Stephen Flaxman ’88 Proudly Supports Windward as Alumnus and Alumni Parent of Natalie Flaxman ’25

In the early 1980s, a middle school boy in Long Island was “falling through the cracks” of the North Shore public school system. His school could no longer support his learning disability, and he would need to move away from his mom, stepfather, and brother and his native Nassau County to Harrison, NY.  

“Back then when I lived on Long Island, anything past Throgs Neck Bridge was considered upstate, and I didn’t know a soul,” recalls Stephen Flaxman ‘88. 

Nearby the house he now lived in with his father, stepmother, and two stepbrothers was “a small school that could help him.” Little did he know, he would return to this now much larger school 30 years later with his daughter in tow. 

“There was a stigma about going to Windward in the 80s, so when I told someone I was going to Windward because I had a learning disability, they thought I was an idiot,” said Stephen. “Right now, if you tell a family that your kid is at Windward, they say ‘that place is amazing!’ But back then, that wasn’t the case for a school for kids with learning disabilities like me.” 

Stephen entered his first day of school nervously, knowing no one. As a newcomer to Windward’s high school [Ed. Note: Windward phased out grades 10-12 in 2004 to prioritize early identification and remediation], Stephen was one of seven students in the entire ninth grade and an entire school of 100 students in grades 1-12. 

Occupying the basement level of the first Windward campus at 13 Windward Avenue, high school students were in mixed-age groupings and were taught by some still-familiar names, such as former Director of Admissions and Assistant Head of School Maureen Sweeney, who was Stephen’s math teacher, and Director of Health, Physical Education, and Athletics Marilyn Hunt, who was his PE teacher.  

“Windward really understood all of us, and the teachers knew our strengths and weaknesses,” recalled Stephen. “Everyone at Windward really put in great effort to get us all where we needed to be, and the attention was amazingly individualized.” 

Windward impacted Stephen both academically and socially—he chats weekly with Drew Teich ‘88—and following his graduation from Windward in 1988, Stephen went on to pursue his undergraduate degree. He began at Southern Vermont College before transferring to attend Manhattanville College and Westchester Community College at the same time, while simultaneously working a job.  

He returned to Windward a few years later to visit, and he made his first donation to the School. Although he was not far along in establishing himself in his career, Stephen felt it was “important to give back, because Windward is an incredible place, and being at Windward was a gift.” 

Stephen married his wife, Susan, and they had two children together. When their daughter, Natalie Flaxman ’25, was in fourth grade, it became apparent that she was having trouble with reading.  

“I had a feeling that something was going on because school was really difficult for me,” said Natalie. “I had issues with inferencing and foreshadowing, so if something was not in the text, I didn’t know it. Every day, I sat in school, and then I had 2-3 tutors after school. Having a learning disability was affecting me socially, too, because of my trouble with inferencing.” 

Natalie’s teacher suggested the Flaxman family consider sending her to Windward to remediate her reading difficulties. They went through the admissions process, and Natalie was accepted to join the sixth-grade class in 2018. 

“When I was younger, my dad never talked about his learning delay. He talked about going to Windward, but I didn’t understand that Windward was a school for people with learning disabilities. It didn’t click for me that both me and my dad have learning disabilities until I started at Windward,” said Natalie.   

Reflecting back on Natalie’s first day at Windward, which was 30 years after his graduation from the School, Stephen became emotional. 

“I was very fortunate to be at Windward. The School taught me a lot of things, like how there are other people like you, and that it’s okay to be different. Although Windward today has so many more resources than it did when I was there, everyone cares about the individual and knows the best way to educate kids with learning disabilities. Natalie was scared because she didn’t know anyone at Windward, but I told her that was the same way for me, too. I took the journey, and now it was her turn,” said Stephen. 

Natalie spent multiple years at Windward, and she graduated in June 2021 alongside 152 other Westchester Middle and Manhattan Middle School eighth-graders, 33 years after her dad. She found classes at Windward to be much easier and suited to her learning needs. Socially, she also developed strong friendships with others who she felt could understand and relate to her language challenges.  

Although she is looking forward to transitioning to her next school in the fall, Natalie will miss Windward and the special ties that she and her dad have at the school.  

“There’s this picture of my dad on one of the walls from when he was at Windward, so whenever we would pass by it in the hallway, my friends would joke and say, ‘Hi Mr. Flaxman!’” said Natalie.  

“Knowing that I’m on that wall, I can’t tell you what that means to me; it’s such an honor,” said Stephen. “I do what I can to give back to Windward and represent the school, and I believe Natalie will do the same. Once an alum of Windward, always an alum of Windward.”