A Falcon’s Journey highlights alumni who have returned to serve the district where they once learned, giving back to the community that helped shape them. This profile features Mr. Holland, a proud Woodlands High School graduate whose path ultimately led him back to the very halls where his own journey began.
For Mr. Holland, coming to Woodlands was not always the plan. After moving to the area from Mount Vernon, he expected to attend nearby Stepinac High School. But a realtor encouraged his mother to take a look at Woodlands instead. Once she saw the school, she knew it was the right place for him. It was a moment that reflected something Mr. Holland still carries with him today - a belief his mother often shared: we are put in places for a reason. Keep your eyes, ears, and heart open, and that reason will reveal itself.
Years later, that belief would take on new meaning.
As a student at Woodlands, Mr. Holland built friendships, memories, and connections that remain part of his life today. He even met his wife during his time at the school. But it wasn’t until he returned years later that he fully appreciated the depth of those connections.
Walking the halls again as a teacher brought an immediate sense of nostalgia. The photos, trophies, and traditions felt familiar. One display in particular still catches his eye whenever he passes it: a trophy of the 1985 Section B football champions.
“My teammates and I had pushed for that coaching staff when we were here,” Mr. Holland said. “They brought them in the year after I graduated - and then they won. I’m still a little bitter,” he admits with a smile.
Today, those memories intersect with his work in meaningful ways. Mr. Holland often hears familiar last names among his students and soon discovers he is teaching the children, nieces, or nephews of classmates he once knew. It reinforces something he deeply believes about the district.
“It’s a real community here,” he said. “These kids have grown up together. They’re like siblings, and at the end of the day, they’re watching out for each other.”
That sense of community reflects something else Mr. Holland believes strongly: that raising children is a shared responsibility.
“It really does take a village,” he said. “When we come together around our kids, that’s when they thrive.”
Interestingly, Mr. Holland did not initially see himself becoming a teacher. After graduating, he pursued filmmaking, earning his Master of Fine Arts from New York University with a focus on film. But while volunteering at a local Youth Bureau, teaching young people how to write and create films, something unexpected happened. One of his fraternity brothers noticed how naturally he connected with the students.
“He told me he thought this might actually be my calling,” Mr. Holland recalled.
The comment stayed with him. Not long after, Mr. Holland began teaching at the Roland Patterson School in the Bronx, working with students in grades five through eight. He later became the school’s Dean of Students, deepening his work with students and families. Then came a call from two familiar voices: Woodlands teachers Mr. Sam Washington and Ms. Wendy Chavez.
“They told me I should apply,” Mr. Holland said. “I was intrigued, since it was my high school.”
Returning to Woodlands felt both familiar and meaningful. But what has mattered most to him is the opportunity to build relationships with students and help them grow. Mr. Holland teaches World History, but he sees his role as extending far beyond the content of the course.
“I want students to learn about themselves,” he said. “I want to be someone they trust.”
His classroom reflects that philosophy. Students are given agency in planning their work and managing their time, more like a college-style course with a syllabus that encourages independence.
“Closed mouths don’t get fed,” he often tells them, a reminder that students must advocate for themselves and speak up when they need support. Time management, responsibility, and self-awareness are lessons he hopes will stay with students long after they leave his classroom and often reflects on a quote attributed to Albert Einstein: Education is what remains after one has forgotten what one has learned in school.
For Mr. Holland, that idea captures what matters most about teaching. “Life lessons and learning how to learn; those are the things that stay with you,” he said.
His work has not gone unnoticed. Recently, Mr. Holland was recognized as an honoree at the Westchester Alliance of Black School Educators’ Winter Wonderland Scholarship Fundraiser, which celebrates Black male educators whose leadership, advocacy, and service extend far beyond the classroom. But for Mr. Holland, the most meaningful measure of success is simpler.
Woodlands is also now part of his family’s story in another way. His daughter is one of his former students and a Woodlands graduate, Class of 2021, continuing a connection to the school that now spans generations. “Woodlands proved to be a good fit for her,” he said. “I’m proud to have had her be educated here.”
“When students leave,” he said, “I hope they got what they needed from me to succeed at the next level, whatever that level is for them.”
At Woodlands, the place that once shaped him as a student is now the place where he helps guide the next generation.And in many ways, the journey feels exactly as it was meant to be.