It was the Tipo 166, introduced in 1948 as a replacement for the 125 S, that first established Enzo Ferrari’s Modenese workshop as a leading manufacturer of racing cars. Powered by a two-liter Gioachino Colombo-designed V-12 engine, the 166 set off a course of development that would define the look, sound, and inimitable character of Ferrari automobiles.

While the earliest 166 Sports and Spider Corsas were successful, it was the 166 Mille Miglia – or MM – that dominated sports car racing in the late 1940s and early 1950s. In fact, the Ferrari 166 MM is the only car to win all three of the great European sports car races – the 24 Hours of Le Mans, the Targa Florio, and the Mille Miglia.

During these early days, Carrozzeria Touring, based in Milan and headed by Carlo Felice Bianchi Anderloni, was the coachbuilder most closely associated with the Ferrari marque. Touring’s exquisite designs and technically advanced Superleggera construction were ideally suited to the sporting qualities of the 166 MM chassis. The now iconic 166 MM Barchetta, or little boat, was the happy result of this collaboration between Ferrari and Touring, leading to the development of a purpose-built competition car – the Berlinetta Le Mans.

Unveiled at Geneva in 1950, the 166 MM Berlinetta Le Mans was a striking fastback with origins in the streamlined Alfa Romeo racing cars of the late 1930s. Sculpted from lightweight aluminum, the beautiful 166 MM Berlinetta Le Mans was, in essence, a more aerodynamically effective Barchetta. Designed specifically for high-speed endurance racing, the Berlinettas featured a business-like cockpit and were purposefully equipped with leather tie-down straps, large external fuel fillers, and lightweight Plexiglass windows. In concept and execution, these early 166 MM competition cars were the foundation for Ferrari’s successful line of dual-purpose Berlinettas.

The Ferrari presented here, chassis 0066 M, is the last of just five 166 MM chassis originally fashioned with Touring’s Berlinetta Le Mans coachwork. Each Berlinetta was unique in its details, and this example, completed in June 1950 and numbered 3462, was originally finished in light blue. According to the research of historian Marcel Massini, 0066 M remained with Ferrari until February 1951, suggesting that it may have been kept as a factory competition car or demonstrator prior to delivery.

The Berlinetta’s first owner, Agostino Di Stefano of Milan, took delivery in March 1951. An amateur racing driver who had successfully campaigned an Alfa Romeo 6C 2500 SS in the 1948 Mille Miglia, Di Stefano did not hesitate to enter his new Ferrari in competition. In May 1951, he took part in the French Rallye d’Aix-en-Provence and then drove the 166 MM in the Österreichische Alpenfahrt, or Austrian Alpine Rally, that June. During his ownership, the Ferrari wore the Milanese registration ‘MI 165421’ and had its bonnet painted a lighter color.

In March 1952, Di Stefano sold 0066 M to a company in Bologna named Stile S.r.l., which owned it only until late August. The Ferrari’s third owner, Astolfo Bertolucci, was another amateur racing driver, who had campaigned an Ermini 1100 in the 1951 Mille Miglia. The 166 MM Berlinetta saw no further recorded competition use until 1953, when it was sold to its fourth owner, Anteo Allazetta of Trieste.

On June 21, 1953, Allazetta drove the Ferrari to a 4th Overall, 1st in Class finish at the XIV Trieste-Opicina Hillclimb, a popular event run nearly every year since 1926. The following month, Allazetta raced the 166 MM at the grueling Coppa d’Oro delle Dolomiti, finishing the single 304 km lap of the mountain road course in 20th Place Overall and 2nd in Class. In June 1954, Allazetta ran 0066 M one last time, again taking part in the Trieste-Opicina Hillclimb, where he finished 5th Overall and 4th in Class. Following these three outings, he retired the 166 MM from racing and kept it until October 1958, when it was sold to North American Ferrari distributor Luigi Chinetti Motors.

Soon after its US arrival, Chinetti sold 0066 M to David Francis Leopold, a Buffalo, New York-based sportsman who owned and raced several exotic sports cars including a Bugatti, Talbot-Lago, Maserati, and several Ferraris. Mr. Leopold owned the 166 MM for a brief period, then returned it to Chinetti, who in turn sold the car to George R. Smith of Ohio.

The Berlinetta then passed through several owners in the Midwest before being sold, in 1964, to a young aeronautical engineer named Ralph H. Smith. In April 1965, Mr. Smith exhibited his prized 166 MM at the second annual Ferrari Club of America meeting in South Bend, Indiana and sold it later that year upon beginning a doctorate program at Princeton.

During the late 1960s and early 1970s, pioneering Ferrari collector Fred G. Leydorf of Birmingham, Michigan served as 0066 M’s caretaker. Not only did Mr. Leydorf serve as Ferrari Club of America President during the 1970s, but he also owned some of the finest competition berlinettas Maranello ever built, including a 375 MM and a 250 GTO. After carrying out a comprehensive mechanical restoration and cosmetic freshening, Mr. Leydorf exhibited the 166 MM at local gatherings including the 1972 Annual Ferrari Club of America meeting, where it was voted Best in Class.

In a Prancing Horse article, Mr. Leydorf fondly recalled his experience with 0066 M: “It was a truly delightful car to own. The body was a piece of sculpture in metal, and it was a mechanical work of art as well. Its handling was a bit ‘vintage’, and its low-speed performance leisurely (but smooth). An endearing little machine…”

The Ferrari’s next owner was another connoisseur, John R. Bond of Newport Beach, California. That the man responsible for the best years of Road & Track magazine chose to own not one but two 166 MMs – this Berlinetta and a Barchetta (chassis 0020 M) – is a testament to the visceral appeal of these early Ferraris. In 1973, Road & Track published Bond’s profile of the 166 MM pair in the magazine’s famous “Salon” section.

The 166 MMs remained in Mr. Bond’s ownership until 1984, when both of his Ferraris were sold to Tohru Horinouchi, a real estate developer in Yokohama, Japan. The Berlinetta and Barchetta remained in this collection, which also included a significant Ferrari 250 GTO, until 1998, when both cars were sold to classic car dealer Herve Willems and returned to California.

Remarkably, Mr. Willems’ two 166 MMs remained together when they joined William E. “Chip” Connor’s incomparable classic car collection. While in Mr. Connor’s ownership, 0066 M was displayed at the Cavallino Classic and then treated to a full photo-documented restoration, overseen by a team of UK and California-based specialists between 2001 and 2005.

In 2008, the 166 MM was sold at Gooding & Company’s Pebble Beach auction to the current owner, a California-based collector with a passion for fine Italian sports cars. Throughout his 14-year ownership, the Berlinetta has been exhibited at several leading shows, including the Amelia Island Concours d’Elegance where, in 2009, it was awarded the Spirit of Enzo Ferrari trophy. It has also been used as Ferrari intended – on the open road – taking part in several exclusive tours in the US and abroad. Most recently, it successfully completed the Carrozzeria Touring Celebration Tour in 2019 and the consignor reports that the Ferrari performed faultlessly on many long-distance events and has been an absolute pleasure to drive.

Beautifully presented today in traditional Italian Racing Red, 0066 M is simply a jewel of a Ferrari. It is also a genuine example of a rare breed, with Ferrari Classiche certification confirming that it retains its original chassis, body, engine, gearbox, and rear end – a rarity for any Italian sports car of this vintage, let alone a competition Ferrari.

Not only is 0066 M offered with its Ferrari Classiche Red Book, but it is also accompanied by a rare, original-competition toolbox, a proper tool roll, copies of the factory build sheets, and an exhaustive research and history file that contains a report by historian Marcel Massini, correspondence, articles, and period photos.

An early masterpiece by Ferrari and Carrozzeria Touring, 0066 M is a brilliant example of Maranello’s original competition Berlinetta, an important model of which just five were built. Since its completion in 1950, this 166 MM has led an extraordinary existence. Raced in European rallies and Italian hillclimbs by its first owners, it was exported to the US where Luigi Chinetti placed it in the hands of wealthy American enthusiasts. Treasured by early Ferrari collectors like Fred Leydorf and John Bond, and a fixture in three significant private collections since 1984, this car has been featured in the pages of seminal enthusiast magazines like Road & Track and Prancing Horse and numerous books on the marque and model. All the while it has survived the past seven decades unscathed and is well-known and highly regarded among marque experts and is Ferrari Classiche certified.

By any measure, 0066 M is a significant competition Ferrari – one that possesses every quality sought after in a collectible automobile: aesthetic beauty, mechanical sophistication, exclusivity in numbers, racing history, and exceptional provenance. With virtually all 166 MMs held in exclusive private collections, the appearance of this exceptional Berlinetta at auction may be the chance of a lifetime to acquire an important piece of Ferrari’s earliest history.