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Jon Shirley

When Jon Shirley was buying his first car, in the early 1960s, he chose a 1961 4-cylinder Sunbeam Alpine because of the amount of fun he would have driving it. Three decades later, when he began collecting cars, he continued to select models that would be fun to drive. Shirley, a former president of Microsoft, recalls a trip in the late 1970s to the Nivelles-Baulers racetrack outside of Brussels. Watching Ferrari Club members speed through the track’s corners in new Berlinetta Boxers convinced him to collect Ferraris. About a decade later he acquired his first, a 1967 257 GTS Spyder. “At first it was just, ‘Let’s put together a collection of cars that are fun,’ ” he told Robb Report Collection in 2013. “Then it became, ‘Let’s put together a collection of cars that are significant.’ ”

Shirley, who is 77, has 27 cars in his collection. Most of them are racecars and exotic sports cars, with highlights including a 1938 Alfa Romeo 8C 2900B and a 1954 Ferrari 375 MM Scaglietti coupe that was custom built for the Italian film director Roberto Rossellini. Shirley and the restoration specialist Butch Dennison spent more than two years rebuilding the Scaglietti, which last year became the first postwar Ferrari to earn Best of Show at the Pebble Beach Concours d’Elegance. 

Shirley prefers not to discuss the prices he has paid for his cars, but he acknowledges that the cost of the Scaglietti was high, especially given the condition it was in when he acquired it. “At the time, I’m sure people would say that it was the most astronomically dumb amount of money to spend on a car that’s in bits and pieces,” he said. “But I always say the same thing: ‘Yes, but [now] I have the car.’

“In the high-end collector-car world, time solves all purchases,” he continued. “There’s nothing that’s really good that’s [ever] worth less than it was 10 or 15 years ago.” 

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