Delorese Gregoire is the spring-loaded, vivacious founder of Winner’s Camp, a leadership academy for teens on O‘ahu. Her cellphone ringtone, “Celebration” by Kool & the Gang, gives little hint of her hard-knock background. Born in 1946 in Salem, Massachusetts, she boomeranged from one abusive foster home to another—thirteen, all told. The first time she saw television, she was in a hospital: eight years old and mesmerized by images of Hawaiian landscapes flashing on the screen.
From that moment she had a mission. “I told myself, ‘I’m getting out of this hellhole and going to Hawai‘i,’” she says. She took every available job, from janitor to secretary to soda jerk. “When you grow up in the ghetto on the East Coast,” she says, summoning a New Englander’s nasal accent, “everybody is like, ‘Yeah, right. Hawai‘i? Are you kidding?’” But by her eighteenth birthday, Gregoire had socked away $900, enough for a one-way ticket on American Airlines.
The teen boarded the plane with no connections and no plan—only chutzpah and a desire to finally be the author of her life’s script. When the wheels touched down in Honolulu, she says, “I felt chicken skin. I felt like I had finally come home.” Concerned that she had no place to go upon arrival, the flight attendants adopted her. She stayed at their hotel for a few days before finding her own place.
With brown hair down to her hips and a newly acquired tan, the petite East Coaster fit right in amid the Waikiki throngs. It was 1964. Hawai‘i had recently become a state, and large new aircraft had shortened the travel time between the Islands and the West Coast from eleven hours to six. This made the Islands more attractive to many Mainlanders. Gregoire landed a cocktail shift at the Tahitian Lanai. The swanky restaurant catered to servicemen on R&R and vacationing celebrities, including Marlon Brando and Prince Charles. The owner took an instant liking to his unflappable new recruit, who kept her cool even when a customer knocked her and a full tray of food into the pool.
Gregoire found that earning her coworkers’ respect took a little longer. “One girl was a real tita,” she laughs, using the term for a tough local girl. “After a few months, once she learned that I wasn’t just a privileged kid, she befriended me.” Lydia Hansen, a tall beauty from a large Chinese-Hawaiian family, introduced the short, spunky haole to her parents, who immediately absorbed her into the fold. Hansen later asked Gregoire to be godmother to her children. “It was the first time I felt love,” says Gregoire. “I was so appreciative. If I hadn’t come to Hawai‘i, I’m not sure I’d be alive.”
In the midst of the psychedelic ’60s, a young waitress with plenty of cash and no supervision could’ve disappeared down a path of debauchery. Instead Gregoire dived into the local culture: paddling outrigger canoes with the Waikiki beach boys and enrolling in ocean science and Hawaiiana classes at the University of Hawai‘i. At the college she taught Japanese nationals conversational English. Her innovative, confidence-building methods became the basis for the Hawai‘i English Language Program and the university’s first English as a Second Language degree.
In 1985 Gregoire launched Winner’s Camp, a week-long motivational retreat for teens. Campers tackle ropes courses and attend workshops in etiquette and public speaking—skills Gregoire worked hard to develop as an adult. The nonprofit program has received national recognition and produced fourteen thousand graduates. Thirteen years ago Winner’s Camp found a permanent home on Kamehame Ridge. The abandoned Army barracks overlooking Hawai‘i Kai were a disaster. Graffiti covered every surface that wasn’t smashed or rusted through. The challenge of renovating the dilapidated kitchen and dorms didn’t dissuade Gregoire in the slightest. Today they’re clean, cozy and wallpapered with inspirational quotes of her own invention.