As a young boy, Bruce Jenner, now Caitlyn Jenner, used to ride his bicycle to the Westchester County Airport in White Plains, New York. Each visit increased his desire to fly. Becoming a pilot, however, would have to wait until after competing in the men’s decathlon during the 1976 Summer Olympics in Montreal. The intense training and surviving on $10,000 a year allowed him neither the time nor the resources to take flying lessons. Besides, Jenner explains, “It hurts every day when you practice hard.”
At the conclusion of the grueling two-day event, Jenner crossed the 1,500-meter finish line and burst into stardom as the decathlon champion—while breaking the world record in the process. Perhaps more precious than a gold medal, he also won the unofficial title of world’s greatest athlete.
Wasting no time, he began flight training that same year in a Cessna 152 at the Santa Monica (California) Municipal Airport. Jenner says that “learning to fly the airplane was easy. It was everything else one has to learn that was challenging.” He wasn’t too keen about departure stalls, however. “They were frightening; you never knew which way the airplane was going to break.” He subsequently purchased several aircraft, including a Pitts and a Mitsubishi MU–2. “The most fun, though, was the unadulterated joy of flying my ultralight floatplane from my home at Lake Tahoe.”
Jenner says that flying makes traveling an adventure and provides a sense of accomplishment, especially when breaking out of an overcast and seeing a runway “magically appear in the mist.”
In 1985 Jenner purchased an aircraft brokerage firm in Columbia, South Carolina, and changed the name to Bruce Jenner Aviation. He closed shop in 2010, the result of increasing fuel prices and declining sales. “It didn’t help when the Obama administration so harshly criticized Detroit executives traveling in business jets,” Jenner said.
In 2015, Jenner came out as transgender. After 15 years of not being current, Jenner recently purchased a 1978 Beech Bonanza V35B complete with a customized glass cockpit. “This new panel makes it feel like learning to fly all over again.” Throwing her fists in the air in that familiar and victorious fashion, she proclaims excitedly, “I’m back!”
Does being transgender create any problems for Jenner in aviation? “Not really,” she says, “but the issue is there. Actually, I take more heat for being a Republican.”
Who | Decathlon gold medalist; executive producer (television)
Hours | 4,000-plus
Certificates | Private, single- and multiengine land, instrument
Favorite aircraft | “All of the airplanes I have owned, but for the ultimate thrill I most want to fly a North American P–51 Mustang.”
Extra | “My advice to new pilots is that they take flying seriously and operate conservatively, especially with respect to weather. My personal safety valve is an awareness that I never have to be anywhere.”
Photography by Mike Fizer