Medina resident Jon Shirley took home the Pebble Beach Concours d'Elegance Best of Show award for his 1954 Ferrari 375MM Scagliati Coupe.

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It’s been called the most prestigious car show in the nation, and possibly the world. Every summer, the Pebble Beach Concours d’Elegance attracts the world’s most glamorous, extraordinary and rare cars to California.

This year, Medina resident Jon Shirley took home the event’s Best of Show award for his 1954 Ferrari 375MM
Scaglietti Coupe. It was the first time in the history of the competition, which began in 1950, that a Ferrari had claimed the prize, and the first time since ’68 that a post-World War II car won the award.

“It was fantastic,” Shirley says. “I couldn’t believe it. I didn’t go down there thinking I would win. But if any post-war car could do it, this one could.”

The car’s history and record of ownership — known as provenance in the collector world — adds to its mystique and fame. And it probably had something to do with the car’s victory, Shirley says.

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It was built as a competition Spyder for film director Roberto Rossellini. The body was ruined when the car struck a tree, and the chassis was handed over to auto designer Sergio Scaglietti in Italy.

The car became a one-off creation when Scaglietti redesigned it as a coupe, giving it graceful lines while keeping some of its race-car traits. He crafted the shape of the car using thin metal strips as a lattice framework, and then molded the bodywork over it.

After changing owners a couple of times, the car was nearly forgotten. By 1995, it lay dismantled in a subterranean garage in a Paris suburb.

When Shirley heard about the Ferrari, he didn’t know that such a car existed. He had been on the lookout for something unique, and the car fit the bill. He negotiated the sale through a broker, and had it shipped to the U.S. for restoration.

The car’s upholstery was wadded up in a box, most of the internal components were dismantled, and the lights and turn signals were all wrong, Shirley says. The initial restoration took his team 4,000 hours to complete. He declined to say what the car is worth, but he has no intention of selling it.

Shirley, who was president of Microsoft from 1983–90, has a long history of collecting. His garage is a nondescript warehouse on the Eastside filled with close to 30 of the most elegant and rare autos in the world. His first Pebble Beach Best of Show award came in 2008, with an Alfa Romeo 8C 2900B.

“It was just as satisfying [to win this year], but what made this one special was that it broke the mold,” he says.

Cars at Pebble Beach are judged according to class, using a long list of criteria. From there, the First in Class winners are eligible for the Best of Show award. Judges from all the classes cast secret ballots using a gut feeling; there are no defined criteria.

Knowing how far to take a restoration is an art. Cars can receive deductions for over-restoration of the engine and bodywork.

On the underside of the hood, Shirley shows examples of the rough-cut seams and tiny indents where hammers were used to shape the metal. Had they been smoothed over during restoration, the car would not have won, since it wouldn’t have been true to how it was constructed.

In spite of the value and prestige of owning a Pebble Beach winner, Shirley doesn’t consider his Ferrari a museum piece. His attitude about a car: If it gets a little roughed up on the road, so be it.

“My tendency has been to do a restoration if the car needs it, take it to a few shows and let everyone see it, and then drive it,” he says. In other words, don’t be surprised if you see his Ferrari on the road.

“They’re cars. They’re meant to be driven,” Shirley says. “They’re not meant to sit around.”