Red letter day for Letterman Ferrari

Riley Riley

A stunning 1965 Ferrari once owned by talkshow host David Letterman will be one of the main attractions at Mecum’s July Indy auction in the United States.

This stunning V12-powered, 1965 Ferrari 275 GTS has incredible provenance, having also been owned by the former president, COO and director of Microsoft, Jon A. Shirley.

Restored to exacting standards by Bobileff Motorcar Company, the 275 GTS sports a rare Chinetti Motors-installed factory production auxiliary hardtop, making it all the more desirable.

It features the original 3.3-litre V-12 engine that, when fired, makes a symphony of notes that send chills down the spine of close bystanders.

The 12-cylinder work of art from Maranello is mated to a 5-speed manual transmission.

The 275 GTS is drop dead gorgeous with its Nero exterior finish and distinctive Borrani wire wheels, that contrast with a striking bright red interior.

Though often overshadowed by longtime rival Jay Leno, David Letterman, has an affinity for cars and is well noted for buying the best.

As the wise-cracking host grew up in Indianapolis, it’s hardly surprising as he’s always been a big fan of cool cars as well as the Indianapolis 500.

Letterman has also been a longtime co-owner of racing teams in both the IndyCar Series and IMSA.

He has a large collection of cars and is a fan of fast, single-seat, open-wheel cars and sports cars of both the racing and street variety.


Likewise, Jon A. Shirley is a vintage racer and noted art and car collector with a particular focus on Ferraris.

Shirley chose this 275 GTS as one of the cars for his very special collection.

In fact, it’s not a stretch to say that this striking 275 GTS should qualify as a crossover for both his art and car collections.

Even without famous owners, the 275 GTS is one of the rarest of the front-engine V-12 Ferraris ever produced and one of the more desirable examples.

Introduced at the 1964 Paris Motor Show, the 275 GT line was produced in both Berlinetta (GTB) and Spyder (GTS) configurations.

These were groundbreaking cars and the first production Ferraris to employ all-independent suspension.

The 275 GT line featured a ladder-style chassis utilising large main tubes connected by small-diameter cross members to give the cars all-important stiffness in the best Ferrari tradition with improved handling courtesy of the new suspension system.

The 5-speed manual transmission was mounted in the rear end, while the engine was located rearward from previous models to improve front and rear weight distribution.

Meanwhile, 4-wheel disc brakes gave the 275 GTS appropriate stopping power for a car with its impressive performance credentials.

The all-steel bodywork was designed and constructed by Pininfarina.

Documented by Marcel Massini, this 275 GTS was bestowed with the Ferrari Classiche Certification Red Book, the ultimate honour from Maranello.

It’s garnered awards from the Ferrari Club of America, including the 2018 FCA Platinum and FCA Best 1974, as well as earlier V-12 awards and a 2019 Cavallino Platinum award.

The car is one of four Ferraris being auctioned from the collection of Dr Vance Shappley and is sure to go for big bucks.


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