Her-Story
The Legacy of Delorese Malulani Gregoire
Founder. Visionary.
“Be bitter or be better.”
A Life Shaped by Resilience
Delorese’s early years were marked by constant change and challenge. Raised in thirteen foster homes across New England, she learned early the power of choice: to be bitter—or to be better. That decision became the foundation of her life’s work.
As a young girl, she saw a glimpse of Hawai‘i on television and felt an instant connection. Years later, when she finally arrived in the islands, she knew she had come home. Hānai’ed by a local family, she embraced the spirit of aloha that would later define her approach to leadership and education.
Through her own journey of healing and personal growth, Delorese discovered that transformation happens from the inside out. Inspired by that truth, she made it her mission to help others—especially teenagers—find their inner strength and voice.
From Vision to Reality
In 1984, guided by that mission, Delorese founded Winners’ Camp, a youth leadership academy dedicated to empowering Hawai‘i’s teens through experiential learning and positive transformation. Working alongside a team of passionate educators and volunteers, she built a program that blended challenge, reflection, and joy.
Before Winners’ Camp, she had already founded Hawai‘i Study Tours, connecting visiting students and local families through educational and cultural exchanges. That experience deepened her belief that learning is most powerful when it’s lived.
Building a Home on the Ridge
Delorese’s approach to education was anything but traditional. She believed young people learn best through doing, feeling, and connecting—what she called “whole-brain learning.”
Her core values became the foundation of the camp:
- Respect
- Responsibility
- Resourcefulness
- Resilience
- Restraint
These “Five R’s” remain central to every program at Winners’ Camp, shaping the mindset, character, and confidence of thousands of youth.
The Philosophy of a Winner
In 2000, Delorese secured a license from Kamehameha Schools / Princess Pauahi Bishop Estate for the breathtaking ridge-top site between Hawai‘i Kai and Waimānalo. Once a Cold War-era military installation, the property was transformed—through years of volunteer effort—into a living classroom surrounded by sky and sea.
For Delorese, the ridge was more than a location; it was a metaphor. Teens arrived feeling small and unsure, and left with a view from above—literally and figuratively—of who they could become.
A Ripple of Impact
Over four decades, Winners’ Camp has served tens of thousands of youth and families across Hawai‘i and beyond. Delorese’s infectious energy and boundless compassion touched every aspect of camp life—from the ropes course to the morning affirmations, from heartfelt family seminars to the joyful graduation celebrations.
A 2005 MidWeek cover story captured her influence perfectly: “Teaching Teens to Be Winners.” By then, the camp had already reached more than 12,000 students and 600 graduate staff. Today, that number continues to grow as generations of graduates lead in their schools, communities, and careers.
“Delorese, you are a heart-song. The word ‘inspirational’ is not enough … You shine when you’re there guiding those teenagers—who all adore you.” For Delorese, the ridge was more than a location; it was a metaphor. Teens arrived feeling small and unsure, and left with a view from above—literally and figuratively—of who they could become.
Passing the Baton
In 2024, after nearly forty years of dedicated service, Delorese Gregoire officially handed the baton to Jeannette Macaluso, who now serves as Executive Director.
This transition marked not an ending, but a continuation of the movement Delorese began in 1985. Her legacy endures in the laughter of campers, the leadership of graduates, and the living spirit of aloha that guides every workshop, ropes course, and conversation.
“I always believed the greatest thing we could do for our teens was to help them believe in themselves. Jeannette carries that same belief forward—with heart, integrity, and vision.” – Delorese Gregoire
Her Living Legacy
Though officially retired, Delorese remains the heart and soul of Winners’ Camp. Her teachings, songs, and affirmations echo through the valley and in the hearts of every camper who has ever said, “I am a winner!”
Her story reminds us all that one person’s courage can create ripples that last for generations.
This page is dedicated with love and gratitude to Delorese, whose vision turned a mountaintop into a home for transformation, learning, and love.
The baton has been passed—but her light continues to guide us all.