By Rob Howe
April 29, 1996 12:00 PM

UNDER A STEADY DRIZZLE, BY A BRILLIANT WHITE CASKET IN A Backyard two miles from the Northern California coast, a group of mourners is singing “Little Boxes,” the Malvina Reynolds folk song written in 1962 as a lament against conformity. Among other things, the song refers to parents sending their children to the same schools, where they all learned to think the same way and “come out all the same.” They didn’t, of course, and never have. But Jessica Dubroff’s parents were determined that no one would ever say that about their little girl, and no one ever did. The 7-year-old whose body lay in the casket—topped with a model airplane celebrating her love of flying—died four days earlier, on April 11, when she failed tragically in her quest to become the youngest pilot ever to traverse the U.S. Jessica, her entrepreneur father, Lloyd, and instructor Joe Reid were killed instantly when their single-engine Cessna Cardinal 177B plummeted into a residential neighborhood in Cheyenne, Wyo., shortly after takeoff.

Finding some comfort in a favorite song of her daughter’s, Lisa Hathaway, 41, asks that “Little Boxes” be played time and again before the 150 or so guests and reporters accompany the casket to the nearby cemetery where Jessica once rode her bicycle. There, Hathaway sums up her daughter’s brief life: “She knew how to reach into your soul and stay there.”

What might have been a joyous occasion, celebrating a little girl’s triumphant cross-country flight from Half Moon Bay, 40 miles south of San Francisco, to Falmouth, Mass., turned instead into a wake, following a tragedy that has loosed a flood of tears, angry criticism and endless speculation. There is evidence that Jessica’s plane was too heavily laden to take off safely at Cheyenne’s high altitude and that the weather that day—which included wind, sleet and thunderstorms—was too rough for small aircraft. But the most anguished questions have been about Jessica, her parents’ judgment and whether children should be allowed to fly planes.

Last week, while experts searched for technical reasons for the crash, many people assigned a deeper responsibility to Jessica’s parents. Some accused Lloyd Dubroff of embarking on a reckless publicity stunt that exploited his daughter. Others, especially those close to the family, argue that though her parents hadn’t lived together since 1990, Jessica was gifted with a full-time mother and a loving, attentive father. However unconventional they may have been, say friends, Hathaway and Dubroff taught their children that little in life is more important than fulfilling one’s dreams. “Everybody’s saying a 7-year-old shouldn’t do this. Why not?” asks Ben Hathaway, 36, Lisa’s brother, a bread salesman from Wareham, Mass. “Before it crashed, everybody was behind Jessica. I’m still proud of her.”

Little in Jessica’s short life fell within the confines of convention. She never attended school, had no children’s books, watched no TV at home, played with no toys, numbered more adults as friends than children and was a vegetarian who snacked on red bell peppers, not M&Ms. But whatever advantages Jessica did or did not have as the child of an idealistic New Age mother who calls herself a spiritual healer, her last months seem to have been nearly idyllic.

Seeking the calm of country life, Hathaway last year moved Jessica, her sister Jasmine, 3, and their brother Joshua, 9, from Palo Alto, Calif., to Pescadero, a tiny town of mom-and-pop shops and clapboard houses nestled in a patchwork of farms between the California foothills and the Pacific. There, Hathaway rented a $l,600-a-month two-story home (with help from Dubroff, who had started a new family) and fashioned a New Age universe for her children. Jessica, whose bedroom looked out on a field of grazing cows, quickly adapted and made friends. “She was an adventurous little girl,” says postmaster Neil O’Leary, who admired Jessica for sending $21—half her monthly allowance—to a relief group for children. “She was encouraged to do whatever she wanted—to reach for the stars.”

As part of Hathaway’s philosophy of allowing the children to forge their own way in life, she. refused to enroll them in school and educated them herself. “School is an unfit place for my children,” she says, arguing that students are not treated as individuals. “The language is unfit. The relationship between teachers and students is unbalanced.” Hathaway, who has not worked for several years, also indulged her kids’ nonacademic interests, arranging for piano, trumpet and riding lessons, even when money was tight. Kelly McKnight, owner of a 70-acre horse ranch up the hill from the Hathaway house, remembers the day eight months ago when he spied Hathaway, with Jessica and Joshua in tow, heading toward his farm.

McKnight, 36. a former stockbroker with two children of his own, was at first flustered by Hathaway’s unorthodox parenting style. When helping McKnight teach Jessica riding, “she’d say, ‘Be with the pony with all your spirit and self,’ ” recalls McKnight. “It was a little frustrating for me to develop a vocabulary that worked for those kids. But it also made sense to me. You have to communicate nonverbally with horses. You have to ‘be’ with the horse.” Like many girls, he adds, Jessica fell in love with the ponies—especially Buttercup and Moonie. She regularly slipped Moonie, an older horse, an extra scoop of grain at feeding time.

But McKnight was rebuffed when he offered Jessica books that his 7-year-old daughter, Devon, enjoyed. “Lisa said, ‘We don’t read children’s books. Can you bring out something more technically oriented?’ I was like, whoa, wait a minute,” says McKnight. But he complied, offering the children equestrian magazines and quizzing them later “to be sure they were reading the contents.”

“Children’s books are lies,” says Hathaway, who was diagnosed as dyslexic as a teen and hated the speed-reading lessons her mother made her take. “They wire up children to think in a twisted way.” Employees of Coast-side Books in Half Moon Bay, though, recall Joshua and Jessica sneaking an occasional longing glance at the kids’ section. “My feeling is children read children’s books and learn from them,” says one employee. “Her view was they should read adult matters.”

Chris Dutsch, who owns a wood-carving and sign-painting business next door to Hathaway’s house, was frequently visited by Jessica and Joshua, who made a pillowcase and a canvas bag for him. “They didn’t have toys, they had tools,” he says. He was also impressed by their diet. “They didn’t get milk shakes and Cokes, they got fruit smoothies and health food,” says Dutsch. “I got a lecture from Jess about eating meat.”

Though Lloyd Dubroff supported Lisa’s lifestyle and encouraged Jessica’s interests, he was not a committed New Ager like his former live-in partner. Born in Brooklyn in 1939, Dubroff moved to Altha, Fla., with his parents when he was a boy. His father, Daniel, now 84, set up a small family farm cultivating tung nuts, which are used to make paint products. “Lloyd grew up with hard physical labor and all the discipline that goes with that,” says Bruce Handler, a former business acquaintance. Once a member of Future Farmers of America, Dubroff studied engineering at Florida State University and the University of Florida, but never graduated. Nor was he allowed to join the Air Force, where he hoped to learn to fly, because at 6’4″ he was too tall, says Handler. A life insurance salesman in Tallahassee, Dubroff was transferred to the San Francisco area in 1968 with his wife, Lane Gourlie, and two children, David, now 36, a retail manager in Concord, Calif., and Deborah, 34, a student.

By the time he and Hathaway met through a mutual friend in 1984, he had divorced and dabbled in real estate and management consulting. “Lloyd was a big thinker, an entrepreneur,” says Ruth Schwartz, who hired him as a financial adviser when she started a travel business in San Francisco. “Sometimes his ideas worked out, sometimes they didn’t. He was always looking for an opportunity to make money.” Through it all, Dubroff was the “kind of man who made you feel like you were the most special person in the room,” says De Eggers, who met him in the late 1960s, when she and Dubroff worked together at an Oakland psychiatric outpatient clinic. Although Hathaway never married Dubroff, they lived together for six years and considered themselves a family. Dubroff asked her to marry him, but, says Hathaway, “I didn’t see the purpose of marriage. I was already wedded to him.”

“Sometimes he did things a little differently,” says Harold Dill, 73, a former associate of Dubroff’s. “Every genius I’ve ever known has had flaws. Lloyd was definitely a genius with flaws.” Genius or not, Dubroff was the defendant in several suits and small-claims complaints over such debts as back rent, taxes and car repairs. (In 1993 he declared bankruptcy, as Hathaway had done eight years earlier.) Some say he was just reckless with money. One former coworker says, “Lloyd was very good at configuring things, going out on the limb and then sawing the limb off.”

But even critics of Jessica’s parents concede that their children were remarkable. Joshua and Jessica were born at home in tubs of warm water intended to ease the trauma of birth. Hathaway, who graduated in art history and studio art from Framingham State College in Massachusetts, says her philosophy, including vegetarianism, was inspired by giving birth. “I saw a peace and joy I didn’t know,” she says. “I got to see their perfect, beautiful bodies, and I knew what I was eating didn’t work.”

Jessica’s parents broke up a year and a half after her birth. Hathaway concedes that Dubroff tired of her demands that he follow her unorthodox approach to child-rearing. In 1991, Dubroff married Melinda Anne Hurst, then 19, and moved to a three-bedroom home in Palo Alto, where his daughter Kendall, now 4, was born and from which they were later evicted for not paying rent. Despite the split, Dubroff and Hathaway remained close—so close that Hathaway and her two children lived for at least two months with Dubroff and his new family. “It was, to say the least, a very unusual arrangement,” says one neighbor. “We didn’t know what to make of the situation.” Another says he “never saw an ex and a current wife on such good terms.” Melinda “accepted [Dubroff’s] other children like they were her own,” claims Eggers.

In March 1992, Hathaway, the fourth of five children of a Wareham postman and his wife, a phone company employee, moved back east to Falmouth with Jessica and Joshua to be near her ailing father. They stayed until 1993, with Hathaway focusing on educating her children and teaching them the value of work. Together, Hathaway, Joshua and Jessica—all on bikes—delivered a twice-weekly local paper. “They loved it,” says former neighbor Joe Girouard. “You’d drive by and see them stopped at the side of the road looking at a snail or whatever.” When a bank repossessed their rented home from the owner, Hathaway attempted to purchase it herself, spreading a sheet across the front of the house that asked, “Will Someone Help Us Buy This House.” No one would.

In December 1992, Hathaway squeezed into her tub and delivered Jasmine, her third child with Dubroff, with whom she had visited since her move east. Girouard learned the news from Jessica, who knocked on his door and said, “My mom had a baby girl. Do you have a scale to weigh the baby with?”

Hathaway returned to California the following year, moving into a loft in Palo Alto so the children could be near their father, who had moved with his family to San Mateo. Lloyd was doing better financially, running a management consulting firm advising companies on planning and marketing strategies. Ruth Hart, a neighbor, took an instant liking to Jessica and Joshua, who visited often. “They’re working kids,” she says. “If I was pulling weeds, they’d come and pull weeds with me. Sometimes they’d just sit on the porch with me and chat. It was just like talking to adults.”

Much to his initial surprise, flight instructor Joe Reid came to feel the same way. Four months ago, Reid, 52, a stockbroker who gave flying lessons out of Half Moon Bay, was approached by Hathaway, who said her children wanted to learn to fly. A deeply religious Vietnam veteran, Reid was “a total contrast” to Dubroff and Hathaway, says George Auld, who was part owner with Reid of the plane that crashed in Cheyenne. Yet Reid quickly bonded with Jessica, his youngest pupil ever. “They both loved flying and they had a love of life and people,” says Auld. “It was amazing when you watched them together. Joe was always happy and smiles.” Though Joshua dropped out, “Jessica was looking forward to every lesson they had,” says Ana Reid, 51, Joe’s wife.

Jessica logged 35 hours before the April 10 flight. Ana Reid says it was Hathaway who broached the idea of a cross-country flight with Joe. She says her husband added, “The dad really wants to do this.” Hathaway and Dubroff managed the project, though they consulted with Joe and Jessica on the schedule and flight plan. Hathaway says that Dubroff promised to take care of the estimated cost of $15,000 for fuel, stopovers and Reid’s time. Reid, who had few reservations about the venture, “just figured he would be there always on the right seat like a prolonged lesson,” says Ana, a teacher’s aide with two grown sons. In fact, Reid took the controls when Jessica took a nap en route to Wyoming (thus ending her chance for a record), and Reid is believed to have tried to save the plane before it crashed the next morning.

Several weeks before the flight, Dubroff faxed the Guinness Book of Records in hopes Jessica’s achievement would be formally recognized. But lie was told the publication had eliminated its youngest-pilot category. Dubroff also had 200 caps embroidered with his daughter’s name to give friends and relatives. The day before beginning her ill-fated trip, Jessica found Chris Dutsch in his studio. “I’ve got a hat for you,” she told him, presenting him with a cap and a smile.

Two days later, on the morning of April 11, an icy storm whipped past the ranch-style home of Harry and Vickie Golden more than 1,000 miles away in Cheyenne. The Goldens and their daughter Mindy sipped their morning coffee, passed the paper and wondered aloud whether it made sense for a 7-year-old to pilot a plane. “I said to my mom, ‘I hate those small planes,’ ” recalls Mindy, 22. “Two minutes later we heard the thunder and then the boom.” The Goldens were among the first to arrive at the crash site, a half-block from their home. “I’ll never forget the red bag, like a duffel bag, just strewn around,” says Vickie, 47. “All these hats were all over the ground.” Meant to be mementos of a glorious flight, they read, “Jessica Whitney Dubroff, Sea to Shining Sea, April 1996.”