Jumpseat: A Vintage Weekend

Though Raymond Cabañas maintained a sober tone during the briefing, his barely perceptible grin offered a hint of mischievousness, most likely a character trait inherited from his late father. A respected airshow performer and fixture in Key West, Florida—his bright-red Waco a perpetual part of the local skyline—Freddy Cabañas had logged over 24,000 hours of flight time in a potpourri of airplanes before tragedy struck in Cozumel, Mexico, while filming for a Mexican reality TV show in January 2013. Freddy and his Mexican photographer passenger died after crashing in a Super Decathlon.

Raymond had been following in his father’s footsteps from the day he could reach the controls of an airplane, but the family sold the air-charter/airshow business a short time after the accident. He pursued a more stable and safer career path to raise his son—employed for five years now as an Atlas Air Boeing 747 first officer. He keeps the door open to his former life by maintaining his International Council of Air Shows qualification as an air boss. That being said, it was hard not to notice the gleam in Raymond’s eye when he watched a Pitts Special perform a perfect Cuban eight.

I scanned the expressions around the large conference table as Raymond’s casual briefing progressed. Most were relaxed, focused on their separate tasks. The performers included the T-6 AeroShell Aerobatic Team, Chef Pitts and his S1S Pitts Special, Thom Richard of Warbird Adventures flying a P-40, and Patty Wagstaff with her Extra 300. The Coast Guard presented their role as an emergency resource and marine patrol. The FAA safety inspector, Lizette Padilla—a former American Eagle pilot with almost the same amount of de Havilland Twin Otter experience as myself—appeared assured that safety concerns had been addressed. All participants were professionals, comfortable with an operation they had participated in countless times. The casual atmosphere reminded me of cockpit briefings from my former life.

The airshow was part of Ocean Reef’s Vintage Weekend, which was introduced 25 years ago with just vintage yachts as a way to showcase the community. It remains one of the rare opportunities for the public to visit the private enclave. The event includes cocktail parties, lunches, first-class goodies and a costume-themed dinner. The itinerary is choreographed and executed better than one at a five-star resort (a comparison that members shun). Automobiles were added to the event and then, eventually, airplanes. Ocean Reef is an exclusive community at the very northern tip of Key Largo that was purchased in 1945 as a fishing camp through the vision of two Minnesota residents, Morris and Alice Baker. A golf course was added in 1955 for the days the seas didn’t cooperate with a rod and reel. A 2,000-foot airstrip was constructed the following year. The runway is now 4,400 feet long, accommodating most medium-size corporate jets, but it’s a VFR-only approach.

Membership at Ocean Reef takes various forms from Equity to Social. The population consists of approximately 1,500 homeowners and 2,300 social members. Homes range in price, with a handful of properties north of eight figures. Boat slips sometimes exceed a seven-figure price tag. Regardless, what really defines the community is the friendly nature of the members. Most seemed genuine and inviting despite the weekend invasion.

For the past nine years, Lenny Sikora, an Ocean Reef resident and experienced GA pilot, coordinated the airplane static displays, pilots and airshow performances. Additionally, he hosted a dinner for a cast of about 100 characters at his home. Lenny’s smile is warm and welcoming. When I inquired as to whether these quality airshow acts—considering that one of them cost upward of $18,000—were financed through the proceeds of event admissions, the response was that a member had simply written a check. As pleasantly unassuming as Larry presents himself, I wouldn’t be surprised if past events involved his funds for at least some aspects of the airshow.

As six degrees of separation would have it, Lenny had maintained a relationship with a young friend of mine from Summerland Key who had sought my marginal career advice when my wife and I lived in neighboring Cudjoe Key—in what seemed a lifetime ago—in the days when I commuted the three-hour drive to KMIA. Ken Wells had approached me as a wide-eyed 19-year-old afflicted by the aviation bug. He grew up around Summerland Key Airport (FD51) and became an airport bum.

For those not familiar, the airport is a unique fly-in, boat-out airpark community. Its most notable resident is Mark Baker, president of the Aircraft Owners and Pilots Association. Having also started my career as an airport bum, I had an affinity for Ken and his ability to enthusiastically curry favor with anyone who would afford him the opportunity to fly an airplane. Mowing the airpark property was only one example of such favors.

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In Ken’s world, four years of college was not in the cards. To that end, he expressed concerns that his airline goal would be hindered because of the educational qualifications required by some carriers, so he set his sights on employment as a regional pilot with the expectation that it would happily be the epitome of his career. My recommendation was to pursue higher education on a part-time basis once hired by a regional.

Eventually, Ken’s ability to easily establish friendships, his good old- fashioned persistence—and a little dose of luck—landed him employment with American Eagle at the age of 21. Because of the pilot-shortage environment, Ken advanced rapidly from turboprop to turbojet, from copilot to captain, and finally, via the flow-through agreement, to American Airlines as a Boeing 737 first officer at the age of 33. This, of course, is an abbreviated version of his career. Apologies to Ken for the abuse he will suffer from friends as a result of publishing this column, but he is among my list of aspiring airline pilots worthy of their enviable profession.

One additional note is that Ken and Raymond attended high school together in Key West and have remained close friends, sharing a list of escapades that should probably not be repeated. Ken was in attendance for the weekend to “shadow” the air boss as his backup, with the future plan of obtaining his own qualification.

Accompanying Ken for the weekend was Nila, who owned a Grumman Yankee. Nila had given up a career in the chemical industry to pursue her professional-pilot dream. To fund her flight training, she is employed as a Key West bartender.

The announcer for the performances was Herk Strumpf, whose day job is regional sales manager for FlightSafety International. Herk owns a Stinson but flew into Ocean Reef with his Piper Cherokee 235. After dropping a few names, we discovered mutual acquaintances. Herk became an instant celebrity, attracting a crowd of admirers after the airshow.

Vintage Weekend at Ocean Reef is certainly a unique experience. What made the event even more gratifying was the reminder that six degrees of separation may actually be only one degree for those of us who share the passion of aviation. I’m hoping for a repeat opportunity.

This story appeared in the May 2020 issue of Flying Magazine