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Lot 21
1938 Bentley 4 1/4 Litre Boattail Speedster

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CHASSIS NO: B161LE

• “The Black Prince” created by the world-famous collector, car builder, Gary Wales
• Exotic, one-of-a-kind, hand-crafted design
• Dozens of unique features
• Featured in many publications
• One of the most famous Bentleys in the world


4,257 cc OHV inline six-cylinder engine, twin SU carburetors, 125 HP at 3,800 RPM, four-speed manual gearbox, four-wheel drum brakes, semi-elliptic leaf springs


From the world-famous collection of Gary Wales of Woodland Hills, California, this spectacular 1938 Bentley 4 ¼ Litre, known as “The Black Prince,” is a tribute to Edward of Woodstock (1330-1376). The “Black Prince” of Wales, is one of the most interesting and unique Bentleys on earth. Mr. Wales is an internationally known creator of unique and finely crafted custom prewar cars, including the famous and magnificent Le Besteoni series of cars, and his creations have been featured in many publications, as well as on Jay Leno’s Garage TV show.

A new generation of Bentleys defined the marque in the 1930s, with the 4 ¼ Litre amongst the most beloved. By the mid-’30s the 3½ Litre Derby Bentley needed more capacity to reliably run at high speed on new continental roads. After supercharging was rejected by W.O. Bentley, who road-tested the prototype, the engine was increased to 4,257 cc, its bearings upgraded, twin SU carburetors fitted, the compression ratio raised and the camshaft reprofiled. Sales literature for the 1936 launch called it ‘The Silent Sportscar’, boasting its 96-mph top speed. The 4¼ Litre gained a special place among Bentley enthusiasts, with many becoming family heirlooms and rarely changing hands.

This 1938 Bentley is a marvel to behold, both in terms of craftsmanship and design. The styling of “The Black Prince” is decidedly prewar inspired, though the body was built to Mr. Wales vision. Its dramatic black body and tailfins are striking to see, and one could imagine it was originally commissioned by a British Royal who was the “black sheep” of the family, and perhaps only drove it at night, at high-speed. Wales wanted to design an element that no one had ever created before on any automobile. Some of the many special features of this vehicle include the engine and transmission moved back 18 inches for a perfect 50-50 weight balance, the shifter moved to the center of the cockpit and an original 1928 Bentley 4 ½ Litre Le Mans racer radiator was fitted. A totally new body was designed utilizing three different types of wood (Honduran, Filipino and African) in the car, including the extraordinary fins carved out of wood and attached so they flow together with the wood covering the rear deck. It also has a unique rear license plate carrier in the shape of the winged Bentley radiator badge. Door handles and step plates were created in cast metal and are totally unique to Mr. Wales’ creations. The very elegant dashboard sports a World War I French aircraft fighter chronometric tachometer, and a special Rolls-Royce magnifier glass speedometer, plus many other special and rare items.

One of the most interesting features of this car is the incorporation of twin side-mounted spare wheels. It is the only automobile to have the doors scalloped around the twin side mounts, missing the wheel by ½-inch giving it a bat wing appearance and allowing for a more compact and pleasing design. This element gives it a most exciting appearance. On the day of its introduction to the public during Pebble Beach week, the entire design team from Mulliner Bentley were so impressed with “The Black Prince” that the design team wanted to display the scalloped doors to everyone at Bentley and invited this special Bentley to go on display at their headquarters in Crewe, England.

Truly a masterpiece of design and craftmanship, a car of this caliber is seldom offered for sale, presenting a rare chance to acquire an automotive treasure.

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