When Classic Airplanes and Classic Cars Come Together

He (or she) who dies with the most toys wins.

The axiom in the subtitle provokes a smile in most of you…or at least a smirk. Not only does it endorse materialism, but it suggests the pursuit of toy accumulation is competitive. Although we won’t admit it, most of us accept that not only is such a pursuit unattainable, it shouldn’t be the focus of our lives. That being said, it sure is fun to dream. I was fortunate enough to spend a day doing just that with one classic Piper Arrow and about 3,500 classic cars.

For a few years I have annoyed my wife with the notion of purchasing a car to match my birth year. The idea was unrealistic. The logistics of storage and maintenance intermingle with the trepidation that such an automobile could only be seen and not touched. After my exposure to the classic car world through my JetBlue captain friend, Mike Strauss, I realized that some toys can be classified as “drivers.” Drivers still have value, but can also be enjoyed beyond the boundaries of a car show on a blue-sky Sunday in June.

With much supervision from Mike and another mutual friend, Kage Barton, a retired Continental/United captain, I was convinced to pull the trigger on my first classic car. The purchase put a grin on my face. As expected, my wife managed a hesitant smile, gracefully acknowledging the acquisition. Interestingly enough, the seller was a spry 90-year-old who had been a Navy aviation electronics technician during the Korean War. He admired pilots, even though we attempted to convince him that he should probably raise his standards. Through him, I soon had the honorable responsibility of becoming the next “custodian” for a 1957 Chrysler New Yorker.

Now in the world of classic cars, I was invited to appropriate events, one of them being the world-famous Mecum auction. There, toys in the form of cars, boats, motorcycles, and engines are displayed for bidding in such utterly ridiculous quantities—from the paint-challenged to the ostentatious—that it boggles the mind. For this year, the auction venues were at 13 locations across the U.S., inclusive of live streaming and a regular TV show. In January, one show took place in Kissimmee, Florida, which presented the opportunity for a 35-minute flight in my classic 50-year-old airplane.

A Friendly Race to Kissimmee

For those who have been following my tale of aircraft ownership woe, the Arrow returned to operational status in December after its six-month retreat in the lonely back corner of a maintenance hangar. An AMOC (alternative method of compliance) was finally granted following the Arrow’s failing an eddy current inspection last year—the result of minor abrasions in the two bolt holes of the right-wing spar cap that were addressed by an airworthiness directive instituted as a result of an accident in 2018. The AMOC simply allowed for bolt holes that were only thousandths of an inch wider in diameter than Piper’s specs. It’s probably the safest Arrow wing in the world now.

With Mike departing in his Beechcraft Bonanza from Ormond Beach, Florida (KOMN), and me departing Flagler Beach (KFIN) in the Arrow, we coordinated a synchronous arrival into Kissimmee (KISM). My non-aviation passenger, Ken Bryan, is a local friend and classic car aficionado. I briefed Ken airline-style—and apologized in advance for any lapse in my piloting skills—assigning him the task of cockpit door opener in the event of a takeoff emergency. Aside from gusty winds, it was a blue-sky morning.

“We landed with minimal issues other than a healthy crosswind. To Mike’s chagrin, we arrived ahead of him.”

Noting that the magenta line took us directly over DeLand airport (KDED) and its associated parachuting operation, I altered the heading to the west so as to avoid a possible encounter with a colorful nylon canopy. My contact with Daytona Beach Approach for flight following revealed a problem with Orlando ATC. They were short-staffed, probably an Omicron-related issue, so no flight following through Class B airspace—an operation the controllers normally accommodated.

Utilizing my new flight-deck assistant, ForeFlight, I began the finger tap dance of determining airspace altitudes and the best frequency for monitoring Orlando Approach. A course to the west of the Class B seemed the best option. Unfortunately, it added an extra 10 minutes to the trek, but Ken was enjoying the scenery anyhow. Disney World, with its permanent TFR, was the next potential airspace violation to avoid. I would find out later that Mike had filed IFR in the Bonanza—with its advantage of ATC routing—so his only complicated task was to find Kissimmee.

We landed with minimal issues other than a healthy crosswind. To Mike’s chagrin, we arrived ahead of him. Fortunately, George Vernon, a former American Airlines colleague and retiree was Mike’s passenger. George bore witness to the winner of our undeclared air race. I don’t remember working that hard on my JFK-to-London flights, but then we didn’t have that kind of fun.

Although the Osceola Heritage Park in Kissimmee was the venue for the auction, you might consider it one of the world’s most expansive automobile museums. The only difference was that the museum pieces were all for sale. In seven hours we only viewed half of the cars.

A Classic Car ‘Encyclopedia’

Mike is a human car encyclopedia, aiding our self-guided walking tour. He has an uncanny ability to procure the most obscure details from body style to the type of carburetor installed. I thought he was just making stuff up, but so far he’s only been wrong twice despite my myriad of questions. He was chastised appropriately for being incorrect.

Performed with the melodic cadence of professional auctioneers, the auction itself was an incredibly efficient process. Most cars rolled onto the bidding stage were there for an average of two minutes. A cherry-red 1959 Cadillac convertible that sold for $155,000 might have taken another minute longer after a bidding war erupted. Although we weren’t seated in the bidding area, I kept my hands in my pockets.

Because we stayed till the end, our flight home was into a night sky. Nighttime flying in a single-engine airplane is not my regular practice—having been spoiled with the luxury of a sophisticated jet and a competent copilot—but I found the courage nonetheless. Without assistance from Signature personnel, having paid the “facility fee” that had literally increased overnight to $50, we walked to our airplanes located at a dark, remote area of the ramp. We removed chocks and orange hazard cones on our own respective walkarounds.

This time with the support of an IFR flight plan, Ken and I launched skyward. We were dazzled by the lights below and a display of fireworks from Epcot. Despite a rheostat failure that didn’t allow for dimming the panel lights, I managed to find the runway back home, albeit with a touchdown that was a little firmer than desired.

It was a great classic car and a great classic airplane day. And no, there’s not a chance that I will die with the most toys.

This article was first published in the Q2 2022 edition of FLYING Magazine.

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