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The Original Bentley Boys

Along with founder W.O. Bentley, the Bentley Boys and their inspirational stories shaped the public image of the marque from the very beginning. Even today, their spirit lives on with the new Bentley Boys.

Inspiring generations. Relentlessly.
Always ready for a race, a challenge or a glass of champagne, the first generation of Bentley Boys were a close-knit group of extraordinary playboys, racers and adventurers who achieved global fame during the 1920s and 30s. They inspired a whole generation of Bentley drivers and admirers, with their passion for driving and deep love of a challenge. And behind the wheel of Bentley motorcars, they dominated Le Mans with five wins in just eight years.

“I don’t think many companies can have built up during such a short period a comparable font of legend and myth, story and anecdote. The company’s activities attracted the public’s fancy and added a touch of colour, of vicarious glamour and excitement to drab lives.”

W.O. Bentley’s words sum up the appeal of the Bentley Boys and their cars to perfection.

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An extraordinary team

The Bentley Boys included former fighter pilot Sir HRS ‘Tim’ Birkin, Harley Street specialist J.D. ‘Benjy’ Benjafield, racing journalist SCH ‘Sammy’ Davis, ‘born adventurer’ Glen Kidston, led by Woolf ‘Babe’ Barnato – all men of independent means. They lived life to the limit, hitting the headlines for their exploits off the racetrack as often as for their performance on it.


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The Hon. Sir ‘Tim’ Birkin

With his blue and white polka dot scarf and neatly trimmed moustache, ex-fighter pilot and baronet Sir Henry ‘Tim’ Birkin was every inch the British sporting hero. Obsessed with speed, he was notorious for being hard on his cars. He persuaded the wealthy heiress Dorothy Paget to finance a team of supercharged 4 ½ Litre Bentleys that became known as the ‘Blowers’. Too fragile for endurance racing, they were unbeatable in sprints with Birkin at the wheel and in 1932 he set an impressive record at Brooklands of 137.96mph.  

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Glen Kidston

Kidston, who won Le Mans in 1930 with Barnato, seemed to thrive on danger. As a Lieutenant Commander in the Royal Navy, he survived two torpedo attacks; as a submariner he escaped after his sub became stuck on the sea bed. He was the sole survivor of a civil airline crash on a flight from Croydon to Amsterdam, re-entering the burning wreckage twice in a brave attempt to save others. Barnato described him as “… the beau ideal of a sportsman. The word fear had been expunged from his dictionary …a man about town when in the mood, a man of action in another.” Kidson’s luck ran out shortly after he’d set an aviation record from England to Cape Town when his borrowed de Havilland Puss Moth broke up in mid-air.

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Dr J.D. ‘Benjy’ Benjafield

Every group of friends has its quiet figure, teased yet regarded with huge affection by the others. Harley Street specialist ‘Benjy’ played this role to perfection alongside his high-spirited teammates. Modest, thoughtful and deceptively skilful, Benjafield wasn’t the fastest of the Bentley Boys, but he had the discipline to follow team orders to get a result. He and Sammy Davis gave Bentley their most celebrated Le Mans win of all in 1927, bringing home ‘Old Number 7’ after the rest of the team had been eliminated in the infamous White House corner crash. In 1928 Benjafield made an equally significant contribution to British motor sport when he set up the British Racing Drivers’ Club.

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John Duff

John Duff was the first Bentley driver to win the Le Mans 24 Hour race in 1924. At the outbreak of war in 1914 he made his way from Lushan in China across pre-revolutionary Russia to enlist. He was wounded at Ypres. After the war ended he took up motor racing and was responsible for persuading W.O. Bentley to take the marque to Le Mans; Duff finished 4th in 1923 with Bentley works driver Frank Clement and won the following year. He retired from motor racing after a serious accident in the 1926 Indianapolis 500. An Olympic swordsman, he taught fencing to Hollywood stars in Santa Monica, USA and doubled for his friend Gary Cooper in sword fighting scenes. In later life he took up competitive show jumping and died after a riding accident in 1958.

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Living legends

Four of the Bentley Boys lived in adjacent apartments in Mayfair’s exclusive Grosvenor Square, where their parties that went on for days became legendary. It was common to see their Bentleys lined up in the south-east corner of the square, leading London cab drivers to refer to it as ‘Bentley Corner’.

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Celebrated around the world

Their fame and exploits meant they were recognised and celebrated wherever they went – even inspiring Harry Craddock, the famous barman at the Savoy, to create The Bentley Cocktail. In 2003, the head barman of the American Bar at the Savoy mixed the Woolf Barnato cocktail in honour of the chief Bentley Boy.

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Breaking records, making headlines.

The Savoy was also the location 
of one of their most renowned celebrations. Following the triumph of a 4 ½ Litre Bentley at Le Mans in 1927, the Bentley Boys were invited to a special dinner at the hotel, hosted by The Autocar magazine. The guest of honour was, of course, the car itself, which became known as Old No. 7 – still dirty and battle-scarred from the race. The Boys sat down to an eleven-course banquet around a horseshoe-shaped table with the car in pride of place in the centre.

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