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Would you pay $100 Million for this car--if you had it?

One of the most coveted cars in the world lost its driver this week when Atlanta millionaire Preston Henn, a flea-market magnate and racing aficionado, died at age 86.

Make no mistake, the 1964 Ferrari 275 GTB/C Speciale could well be the Ferrari, the most rare and storied specimen from a brand built on scarcity and lore. It may also be the world’s first car to break the $100 million mark, provided it finds its way to the auction block.

What is it, mechanically?

Critically, the 275 GTB was designed by Pininfarina, the Italian firm responsible for the bodywork on some of the most coveted Ferraris and Alfa Romeos. When it went into production, Ferrari had recently restructured as a public corporation. For the first time, cars for the road and weekend warrior drivers were no longer solely seen as a way to finance racing teams. Today, cherry versions of the 275 GTB are valued at about $2.4 million.

A few of these machines, however, were built for racing and stamped with a “C”—for “Competizione”—and "Speciale" (lest one think it common). Closer in lineage to the GTO Ferraris that took Europe's racetracks by storm in the early 1960s, the "special" 275 GTBs had thinner body panels and a more spindly infrastructure, a metal diet that trimmed 300 pounds in all. Its engine was mounted lower in the body for better handling. With six carburetors, one for every two cylinders, the car produced 330 horsepower. At the time, that was forza with a capital F.

What is it, emotionally?

To appreciate in multiples, a classic car needs more than good looks and snappy statistics; it needs a good back story—what collectors call provenance. Henn’s Ferrari is layered with the stuff. In 1965 it won its class at the 24 Hours of Le Mans, the World Series of motoring.

For decades, Henn showed no interest in selling the machine. Rather, he displayed it proudly at his Swap Shop, a giant flea market and drive-in movie theater complex in Fort Lauderdale, Fla. (At the moment, the joint is fittingly showing The Fate of the Furious.) A slightly eccentric owner never hurt the value of a car either (see: Joplin, Janis), and Henn falls squarely in that camp. In addition to being a profligate collector, the flea-market magnate ran a racing team and was a respected wheelman in his own right.

"About 10 years ago, he got an offer from a big Japanese collector for 35 to 40 million euros," recalled Ron Vogel, a friend and racing buddy. "I think he responded, ‘Stop talking to me.' "

For Ferrari, he was both a devoted customer and a provocateur. Vogel said Henn repeatedly rejected Ferrari's offers to show the vehicle at its own museum. When Fiat Chrysler rejected his bid to buy the ultra-rare LaFerrari Aperta (and returned his $1 million check), Henn sued the company for defamation. He eventually dropped the suit, telling Road & Track: "It ain't [about] the fucking car."

What is it, financially?

What is Henn's 275 GTB/C Speciale worth? Well, what someone is willing to pay for it. Brian Rabold, vice president of valuation for the Hagerty Group, said it doesn't have the historical racing significance of Ferrari's coveted early GTOs.

But it's a better car and more rare—one of only three.

At auction in 2014, one of its siblings fetched $29.4 million. Rabold said Henn's Speciale would fetch between $50 million and $75 million.

"But there could be someone that surprises," he said. "This is a once-in-a-lifetime opportunity, and I'm certain there are people who have long been interested in this car."

Whether the vehicle finds its way to the market, meanwhile, remains to be seen. Henn is survived by his wife of more than 60 years, Betty, and four children. Before passing, he told Autoweek that he made sure the Ferrari will stay on display at the Swap Shop long after he is gone.

"That was his crown jewel," Vogel said. "At one point he said he wanted to be buried in it."

If you are really keen on Ferraris from the 1960s, pick one up for $200,000—say a 300 GT. At that price, one could justifiably drive it down to Fort Lauderdale and ogle Henn's precious machine for free.

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