His story was legendary: Born to parents who made a life flying and selling airplanes, Leeward "was literally raised on the airports his father operated," according to a profile on his family's website.
Photos: Reno air show tragedy
Leeward's most recent obsession was the "Galloping Ghost," a World War II-era P-51 Mustang fighter he and friends retrofitted for racing.
He excitedly trumpeted the work that had been done on the Galloping Ghost to prepare it for the National Championship Air Races held in Reno. "She's rested but hungry," his website said. "The [reins] are coming off and she's coming out of the stable…. How fast will she go? Hold on tight, you'll find out soon enough."
On Friday, Leeward crashed while piloting that plane during a high-speed race in Reno. Leeward was killed, as were spectators on the ground. Scores of others suffered injuries, some of them critical.
Leeward's family members witnessed the crash, said Reno Championship Air Races President and Chief Executive Mike Houghton.
"They obviously are devastated," he said at a televised Reno news conference. "His wife wanted me to know that Jimmy would not want us to cancel the races." Leeward's pilot's medical records were up-to-date, and he was "a very qualified, very experienced pilot," Houghton said. He'd been racing at the event in Reno since 1975.
News of the crash and Leeward's death left the fervent airplane racing community stunned and deeply saddened. "Everybody knows him. It's a tight-knit family," Houghton said. "He's been here for a long, long time."
Hundreds of people posted messages on Leeward's Facebook page.
"RIP Jimmy," one read. "He left this world with his boots on doing what he loved."
Some angrily questioned why man his age was racing planes. "What the hell was he doing up there over a public venue?" one asked.
Fans at the race said it appeared that Leeward tried to steer the plane away from the stands where spectators were sitting. It is unclear what caused the crash, although officials said initial reports may indicate a mechanical failure.
Leeward ran Leeward Air Ranch in Ocala, Fla., described on its website as a "500-acre private, gated pilot's paradise" where fliers can "experience the freedom of flying far from the restrictive airspace of the big city." He left little doubt that he relished the speed and challenge of racing in a class of planes that commonly exceeded 450 mph. It was no hobby for him. He wanted to win.
"Welcome to the Big League. The 'serious toys for big boys' club," read his website. "You need massive horsepower, a tricked-out airframe, and a great pilot to get past it.…No margin for error here! These guys are always on the edge knowing one wrong move, in one split second, could mean the end."