Lot 243

Monterey 2016

1965 Ferrari 500 Superfast Series I by Pininfarina


$2,750,000 USD | Sold

United States | Monterey, California



Chassis No.
Engine No.
  • The 1965 Chicago Auto Show car
  • One of only 36 examples produced for Ferrari’s best customers
  • Formerly owned by Dieter Holterbosch and Dr. John L. Brady
  • Wonderful original interior, never taken apart; ideal for preservation class
  • Matching numbers throughout
  • Freshly meticulously refinished in the original Blu Scuro color

400 bhp, 4,962 cc SOHC V-12 engine with three Weber twin-choke carburetors, four-speed manual transmission, independent front suspension with A-arms and coil springs, solid rear axle with parallel trailing arms and semi-elliptical leaf springs, and four-wheel hydraulic disc brakes. Wheelbase: 104.3 in.

Please note that Internet bidding is not available for this lot. Interested parties that are unable to attend the sale may register to bid by telephone or place a commission bid online at rmsothebys.com.


Ferrari has a long and grand tradition of building what can justifiably be referred to as supercoupes, a style that is virtually unique to the famed Maranello automaker. Other manufacturers could produce sleek two-passenger coupes that were comfortable and fast, but Ferrari’s offerings were individually hand-built, in extraordinarily small numbers and often with numerous bespoke features. More importantly, they were more than fast: they were some of the fastest automobiles on Earth outside of a race track.

The last generation of the original Ferrari supercoupes was the aptly named Superfast, produced between 1964 and 1966. Featuring updated Pininfarina coachwork with a dart-like tapered nose, gracefully rounded tail, and glassy European greenhouse, it encompassed a highly developed version of the original Ferrari Colombo V-12, now displacing five liters and producing 395 horsepower, an output that was utterly remarkable for the era. The car’s top speed was 175 mph, a figure that could be achieved quite readily and with no particular special treatment on the part of the driver. It was a remarkable performance for 1964 and a top speed that would still be worthy of special notice a decade later.

Each Superfast was also super expensive, retailing for well over $14,000. Buyers were as elite as the car itself, encompassing the foremost Ferrari enthusiasts in the world (something still true of their owners today). Two family members of the Aga Khan, future Aston Martin company owner Peter Livanos, film star Peter Sellers, Woolworth’s heiress Barbara Hutton, and racing driver John von Neumann were among the 36 illustrious and very wealthy figures who acquired a 500 Superfast when new.

Simply put, the 500 Superfast encompasses everything great about Ferrari in this era: incredible beauty, incredible power, and peerless exclusivity, all of it in measures that are as impressive today as they were in 1964.


Only two 500 Superfasts are known to have been displayed at American auto shows, the first of which was the car offered here, chassis number 5985, which was displayed by Chinetti Motors at the 57th Annual Chicago Auto Show between February 20th and 28th. This was only the second 500 Superfast to have been delivered to the United States, and as the first to be publically shown can be credited as many enthusiasts’ first-hand introduction to Ferrari’s latest and greatest supercoupe.

As an early production 500 Superfast, the 6th, Pininfarina job number 99585, has several distinctive and desirable features, including 11-slot fender vents, floor-hinged pedals, and a four-speed synchromesh transmission with a mechanical clutch and electronic overdrive. Completed on 23 December 1964, following nearly nine months of craftsmanship, it was originally finished in an attractive color scheme of Blu Scuro over Arancia leather, which undoubtedly caught many an eye while being shown under the lights at McCormick Place.

Following the Chicago show, Chinetti Motors dealt the 500 Superfast to its original owner, Hans Dieter Holterbosch of New York. The American importer for Löwenbräu beer, Mr. Holterbosch was a passionate collector of the world’s great performance automobiles, owning everything from a Mercedes-Benz W154 and Bugatti Type 59 to superb examples of the Duesenberg Model J and Ferraris 340 MM and 375 Indianapolis. That a collector of the world’s greatest vintage powerhouses chose to buy a 500 Superfast speaks to the cache of this model, even when it was new.

Nonetheless, Mr. Holterbosch returned the car to Chinetti Motors for sale after a short time, and it was sold to its next enthusiast owner, Judge Samuel Simon Leibowitz, a successful criminal defense attorney from Long Island. Judge Leibowitz, like Mr. Holterbosch, loved fine automobiles, in particular Ferraris, and had been one of Luigi Chinetti’s earliest customers; over the years he would own a 250 GT LWB California Spider and an alloy-bodied 275 GTB, in addition to the Superfast.

In 1966 the car was sold by an owner in the posh Detroit suburb of Grosse Pointe, Michigan, to Dr. John L. Brady of Goodrich, Michigan. Dr. Brady used the car intermittently until 1973, at which point it was put into storage in his climate-controlled garage. Two decades later, perhaps recognizing his good fortune to own such an exclusive automobile, he sent the car to the noted Ferrari mechanic Terry Myr of Port Huron, Michigan, for a complete engine rebuild and attention to its braking and fuel systems. In August of 2002, the car appeared at the Concours-Italian Style at the Edsel & Eleanor Ford House in Grosse Pointe, in what is believed to have been its first public display since the Chicago show of 1964!

The car was acquired by its current owner, a renowned Ferrari connoisseur, after 47 years with Dr. Brady; at the time, the car showed just over 13,500 miles and was in solid original condition, with the exception of an older refinish in silver. In fact, such was the car’s incredibly well-preserved order that it still ran and drove well and strongly, as it does today. The consignor recounts that the only work deemed necessary to the excellent low-mileage original 500 Superfast was being refinished in the original color, Blu Scuro. The Arancia leather interior remains wonderfully, fully original, as is the wooden capping of the dashboard; all shows just enough wear to be warmly inviting and is in a remarkable state of preservation for being over 50 years old. Furthermore, the car performed excellently and without issue on the Quail Rally just last year. Today the car remains among the lowest-mileage extant Superfasts, having recorded 14,075 miles, and is still accompanied by a correct tool roll.

Given that only three dozen examples were originally produced, surviving 500 Superfasts seldom trade hands, and usually privately. The opportunity to acquire one with such wonderful history and an exquisite restoration can safely be held among the rarest Ferrari opportunities on the market today. Offered here is one such example, the renowned, extremely original, and beautifully conserved Chicago Superfast—a Ferrari with few equals, then as now.