Kailua Generations

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In Kailua, “My parents were like settlers,” says Deborah Pope. She’s shown here with her father, Bill, circa 1952. The guava tree in the front yard and Olomana marked where she roamed as a child.


The Rodrigues-Pope Clan

Sitting on a picnic table in the backyard of Barbara Pope’s home in Maunawili, one has a near-perfect view of Olomana edging up toward the sky, standing above the faint outlines of former rice fields and farms. It’s easy to imagine Barbara, the owner and principal of Barbara Pope Book Design, and her siblings, Deborah, Gaye and Jeff, spending their “wild” childhood days scampering up Olomana in rubber slippers.

It’s also easy to imagine how this place became the focal point of their lives. “I call it orbiting around Olomana,” says Deborah, the executive director of Shangri La. “It’s like the bellybutton is the grandparents’ place over there, the beach down there, the mountains up there and the homestead over here and life just seems to orbit around Olomana.”

The maternal side of the family hails from Portugal, and came to the Big Island and Kauai between 1878 and 1883. They were plantation laborers for nearly two decades before they moved to Honolulu, living and working in the city until the 1930s, when Barbara and Deborah’s grandfather, Frank Rodrigues, was offered a job at the Kawailoa Training School for Girls in Maunawili, where the family lived in a cottage on school property.

Barbara and Deborah’s parents, Gladys Rodrigues and Bill Pope, met when they were both working at The Honolulu Advertiser. A teenage runaway from rural North Carolina, Bill had traveled to Hawaii from San Francisco in the 1930s aboard a Matson liner and never left. The newly married couple lived with her parents in Maunawili then bought their first home in Lanikai, where they resided until 1951, when they moved to a 5-acre leasehold property in Maunawili. “My parents were both very glamorous,” says Deborah. “My father was a handsome, dapper, well-dressed, redheaded guy with a red mustache. My mother was a beautiful Portuguese woman with dark hair, very well dressed. They were an elegant couple.”

The couple wasted no time in setting up their dream life, adding their son, Jeff, to their brood of three girls, as well as a menagerie of guinea fowl, horses, chickens, rabbits, cats, dogs and a cow.

The popes at Maunawili, around 1955. From left: Gaye, Gladys, Debbie, Barbara and Bill.

“My parents were like settlers,” says Deborah. “They had very different aspirations from my grandparents. Moving up here and buying the five-acre lot was a big deal and, in a lot of ways, it was a dream of theirs.” The Pope kids lived outdoors, spending their days riding horses, climbing giant guava and mango trees, swimming and fishing at a nearby swimming hole with neighborhood kids and hiking the valley barefoot.

“Because we were pretty isolated, we didn’t go into Kailua proper unless we were driven by our parents,” says Deborah. “We weren’t allowed to ride our bikes there.” Attending St. Anthony School in Kailua gave them their first glimpses of town life. “Going to school, which meant leaving Maunawili, and having a whole new circle of friends, sleeping over at friends’ houses and realizing that they could walk to the stores and each other’s houses was really a big revelation,” laughs Deborah. “You know hanging out in Kailua town, smoking cigarettes behind Kailua Theater was really big and fast. It was way too fast for me.”

Their parents later divorced, and their mother sold off the horse pasture and, in the 1970s, subdivided and sold off additional property to purchase the fee-simple interest from Kaneohe Ranch, leaving the family with a little over an acre and a half.

From far left, Genevieve Rodrigues and her sister, Gladys Pope, working at Bellows Air Force Base in early 1942.

Today, the property consists of the Pope’s original house, which is rented out to a family friend, a smaller cottage next door in which their 94-year-old aunt resides, and Barbara’s house in the former horse pasture, which she bought back in the ’90s. Deborah and Barbara spent several years on the Mainland for college, but both felt compelled to return and start families. Deborah now lives down the road in Kalaheo Hillside and has two sons, John and William Foster. According to Deborah, both boys are total water people who love to fish and surf and continue to live and work in Kailua, one in the Legislature and the other as a boat mechanic at Kaneohe Marine Base.

“They both went away to college,” says Deborah. “They referred to going to college on the Mainland as ‘doing time.’ They moved right back as soon as it was over.” Barbara left New York City, returned to Kailua with her husband, architect Fabrizio Medosi, and had a daughter, Marie, a dressage rider based in Southern California who frequently calls home to say that she’s homesick. They suspect that she, too, will one day move back home.

Because the Popes’ mother had the foresight to put the family property into a trust, it’s almost certain that several generations from now a Pope will still be living there. “Even though we’re scattered, [the Maunawili house] is still sort of the navel of the family,” says Deborah. “I got married in the living room here. We had my mom’s memorial service here, and her ashes are interred here. My husband died this summer and we had the memorial service right here. It was the perfect place.”


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