On April 11, 1996, Jessica Dubroff, 7, died in a Cessna plane crash while attempting to become the youngest person to fly across the U.S.

The crash, which also killed her father and her pilot-instructor, also raised questions about her parents' judgment and whether children should be flying planes at all

“They were a wonderful father and daughter who set out on the journey of their lives," Dave Dubroff tells PEOPLE, "and unfortunately there was an accident"

Dave Dubroff still remembers the moment on April 11, 1996, when he learned that his 7-year-old half sister, Jessica Dubroff, and his 57-year-old father Lloyd were killed in a plane crash that also claimed the life of pilot and flight instructor Joe Reid.

“I was at work,” Dave, 66, of Concord, Calif., tells PEOPLE, “and I heard on the radio that the plane had crashed. I ran out to a payphone and called the Cheyenne Police Department, who told me to call the sheriff's department to find out."

"I was in denial and thought, ‘I'm sure everybody lived,' " he says. "Then they told me, ‘No, they had all died on the flight. ‘ ”

At the time, Jessica was attempting to be the youngest person to pilot a plane across the U.S., a feat that drew national media attention — but the crash raised questions about her parents' judgment and whether children should be flying planes at all.

Entrepreneur Lloyd Dubroff moved to the Bay Area in 1968 with his then-wife Lane and their two children, including Dave.

Although Dave says his dad was often busy with work, he was still an attentive father. “He wasn't home a lot,” he says. “But when he was, he was all there.”

In 1984, Lloyd, then divorced, met Lisa Blair Hathaway through a mutual friend. Though they never married, the two lived together for six years and went on to share three children, including Jessica, who was born in 1988.

As reported in PEOPLE's 1996 cover story on the crash, Jessica had an unconventional childhood. Raised by Hathaway, a New Age mother who described herself as a spiritual healer, Jessica was homeschooled and grew up without toys or children's books.

Her mother's philosophy? That children should forge their own way of life.

"Whatever [the kids] wanted, she supported them," Patty Sarabia, a neighbor, told The New York Times in 1996.  "She believed they could do anything."

After his relationship with Hathaway ended (Hathaway later said that she and Lloyd differed over her unorthodox view of child rearing), Lloyd married Melinda Anne Hurst in 1991.

Still, Lloyd and Hathaway remained close and at one point, Hathaway and her two kids, Jessica and her brother Joshua, lived with Lloyd's new family for at least two months. A third child of Lloyd and Hathaway, Jasmine, would later be born in 1992.

Speaking with the Times in 1996, Kelly McKnight, who had a farm where Jessica learned to ride horses, said her interest in aviation appeared to date back to her sixth birthday, when her parents let her take a ride on a plane and the pilot even allowed her to take the controls.

“She was a wonderful kid,” Dave tells PEOPLE, “and of course loved flying. That was her main hobby.”

Dave says his dad was very supportive of Jessica's interest in flying. “That's the kind of father he was,” he says. “Whatever his kids were interested in, he wanted to be involved with them around that activity.”

When Hathaway approached pilot Joe Reid, 52, saying that her children wanted to learn how to fly, he formed a quick bond with Jessica, his youngest student.

As noted in a 1997 NTSB report on the crash, in an ABC News interview with Jessica and her father before the crash, when asked where the idea for the cross-country flight came from, the girl said it originated with her dad.

“I did originally," Lloyd responded. After getting her mother's approval he said he told Jessica she "could think about this a little," but she answered, "No, that's something I'd like to do.' "

By that point, according to the NTSB report, Jessica had logged 33 hours of flight time. She didn't have an FAA medical or pilot certificate, so officials described her throughout the report as a “pilot trainee.”

The trio decided they'd depart on April 10 from Half Moon Bay and arrive at Falmouth, Mass., where Jessica was born, on April 12.

“I thought it was great,” Dave tells PEOPLE about his initial reaction to the trip. “I was happy for them that they were going to live that out. She would've been the youngest pilot ever to have flown cross country and back.”

Chris Reid, the pilot's son, tells PEOPLE that at the time, he never felt the adventure struck his father as outlandish. He says he believes his dad, a stockbroker who took up flying after his military service in Vietnam, saw the adventure as a way to spotlight something he loved: aviation.

“I think Lloyd was like, ‘Yeah, let's go. Can I be part of this?' " Chris posits. “My dad was like, ‘Yeah, great. I've got somebody paying for me to go fly my plane. I got a caregiver for the kid that's bringing the media attention to aviation.' And for Jessica, I know she was like, ‘Hey, I'm just here. I'm doing this and let's have fun.' "

The last time Dave saw his half sister was shortly before the voyage, when he took a brief flight with her behind the controls. "I was amazed," he recalls, "[at] how much in command she was."

Chris, who was actually there when the Cessna took off from Half Moon Bay on April 10 for its maiden voyage, remembers “there was a lot of media."

"I was able to say goodbye to Dad, ‘Hey, take it easy.' He took off and that was it," he adds.

Later that day, the Cessna arrived in Cheyenne where the trio stopped for the night.

According to the NTSB report, Lloyd called Jessica's mother at the end of the flight's first day and told her Jessica slept for part of the trip and that Joe assisted her on one of the landings.

The next morning, April 11, the three headed to Cheyenne Airport to resume the flight, even though the forecast was filled with wind, sleet and thunderstorms.

At 8:24 a.m. local time, approximately four minutes after takeoff, the Cessna crashed, killing all three on board.

Chris was flipping channels for the latest coverage of the flight when he heard the news, then waited by the phone for officials to call.

His dad's funeral service was held four days later in Half Moon Bay. When it was over, Chris and his brother Matthew headed to Pescadero to serve as pallbearers for Jessica's interment that same day.

“They took her casket on a horse and wagon out to the graveyard,” Dave recalls. “That was a really hard service. There were a couple people playing guitars and singing songs."

"It got to be too much for me," he adds. "So I walked away before they lowered her all the way into her grave.”

The tragedy brought scrutiny upon Jessica's parents.

“Before the flight, they were getting positive press,” Dave says. But then, he recalls that instead of being portrayed as a "wonderful father" who helped his daughter realize her dreams, he was called a stage dad and a "bunch of stuff that just wasn't true."

The worst memory Dave has of the media backlash was when he came across a magazine at a newsstand while meeting his uncle (Lloyd's brother) and grandfather at San Francisco International Airport.

”I'll never forget the cover of Time was a picture of Jessica and the words ‘Who Killed Jessica?' " he recalls. "I tried to get in between my grandfather and my uncle and the newsstand, so they wouldn't have to see that. I don't think I was successful.”

About a year after their deaths, the NTSB issued its official report on the crash.

Officials stated that Reid was handling the plane's controls at the time of impact. The probable cause of the crash was the decision to take off in deteriorating weather conditions, with officials noting the plane was overweight and the density altitude was higher than Reid was accustomed to.

"Contributing to the pilot in command's decision to take off," read the report, "was a desire to adhere to an overly ambitious itinerary, in part, because of media commitments."

Chris says the NTSB findings weren't a surprise to his family. “He made a bad decision,” he says about his father. “He risked it going up and trying to get out and punch out and get out above the storm, and it didn't work out… There's nothing to refute.”

Dave says it took a while for him to get over the loss of Lloyd and Jessica.

”For about the first 20 years, the anniversaries were really hard," Dave shares. "I got very emotional."

Then, around a decade ago, he found peace by focusing on how grateful he was for the time they'd been able to spend together.

“They were a wonderful father and daughter who set out on the journey of their lives," he says, "and unfortunately there was an accident."

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Dave says he has no doubt that Jessica would have grown up to be an “amazing woman," while the memories of his dad's love are something he'll always keep close.

“My dad was a very loving, warm, emotional man, and I realized how blessed I was to have had him for 36 years," he says. "So now on the anniversaries, there's just a lot of fond memories."

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