Maybe it’s the word ‘boys’ that makes the phrase ring. We know that they were grown men, but somehow it’s the image of schoolboy larks which cements the legend of the Bentley Boys. It’s rooted in the time, too: the 1920s, when men with inherited wealth didn’t have to work, paid racing drivers were rare and the amateur ideal was still admired.

Who were these grown-up boys? There was no strict qualification: if you were asked to drive for the works you were part-way there, but it was as much an informal social club as a team. We know them now as party-goers; yet they were regular winners. How did these contrasting elements co-exist?

Most of the Boys were Bentley owners already racing their own cars. They loved the off-duty pranks, but they respected team discipline: as WO Bentley said, if they had not, they would lose their place to one of the numerous contenders for it.

“We were fortunate in having a mile-long waiting list which included the best amateurs of the day,” he said. Under WO’s attentive eye the team became extremely thorough – pit routines were even filmed to improve efficiency. Despite the larky image, the Bentley team raced to win, and for serious reasons.

“We were in racing not for the glory and heroics but strictly for business,” said WO. “No-one ever attempted to dispute that competition success was the cheapest way of selling cars.”

Practical jokes and midnight adventures were the code, so it was ironic that this levity had at its core the reticent, moody man who was WO, a man who reacted to adversity with silence and hated to argue. He was nevertheless revered in the firm; if there was friction it was rarely with the drivers. He appreciated the PR value of the Boys, calling them “this nebulous band of drivers, whose club houses were Mayfair and Brooklands and whose 24-hour AGM took place at Le Mans. The public liked to imagine them living in expensive Mayfair flats with several mistresses and several Bentleys. For at least several of them this was not such an inaccurate picture”.

“the public liked to imagine them in smart Mayfair flats with several mistresses and several Bentleys”

WO was selling a touring car, and knew that endurance events such as the BRDC 500 and the Double-12 were ideal showpieces. The perfect showroom, too, for the toughness of Frank Duff. Looking for excitement after WWI, Duff chose motor racing. Big FIATs and a huge Benz were merely tasters before he bought a 3-litre Bentley and decided to break Double 12-hour records at Brooklands. Tall and slender, Duff hardly looked a tough guy, but he swam and ran assiduously and ate a curious health diet, and if anyone smiled as he mixed his honey and eggs, it didn’t cancel their admiration for those relentless hours of forcing his Bentley around that dusty concrete bowl.

In 1923, when a 24-hour race was mooted at Le Mans, it was Duff who took the idea to WO, saying that if the firm would prepare it and lend a mechanic, he’d buy a new Speed model and enter it. Duff wasn’t the first to propose such a plan, but he was a Bentley dealer, he had results behind him, and WO felt they could do business.

To drive with Duff, WO allocated Frank Clement. As a Bentley employee, Clement was the nearest thing to a professional driver, though his racing came on top of his post in the Bentley experimental shop. His thoroughness was behind the details which would make the Bentleys successful: external fillers, quick-action caps and endless pits drill. Though always included in team celebrations, he was not one of the glamour crew with a private income, and was frustrated by the Boys’ collective lack of mechanical knowledge. He enjoyed the fun but found it “a nuisance at times”. He was the only Bentley driver to compete in all the Le Mans entries from 1923-30.

That 1923 exercise was a bit makeshift: they just loaded up the car and drove down to Le Mans. WO and AFC Hillstead, the sales manager, followed by train. Duff’s car performed well, though a holed petrol tank knocked them back two hours; Duff ran three miles back to the pits for aid. They finished fourth.

Duff went back to Le Mans on the same terms in ’24 and this time he and Clement won. Duff’s fastidious preparations had brought Bentley glory at very little cost. After the disastrous ’25 Le Mans, when both cars ran out of fuel, he set more 24-hour records at Montlhéry. He moved to America in 1926, returning in the 30s to breed horses; he died in 1958, falling from the saddle.

Another customer would soon make his mark. A consultant bacteriologist, cheerful, balding, Dr J D Benjafield hardly looked like a playboy. With a lucrative private practice and a wealthy wife his social life involved weekends on his motor boat and visits to Brooklands. After the Bentley’s good showing at Le Mans in ’23, he bought a 3-litre and began to fancy himself as a bit of a driver. But it was Bertie Kensington-Moir, who ran the service department at Cricklewood, who brought him into the fold. Large and cheery, Moir, said Hillstead, “could be very troublesome on occasions,” explaining that while sharing a cabin across to Le Mans in 1924, Moir pitched WO out of his bunk and created a shambles in the room. But WO remembered his “vast good humour and warmth”.

Moir and Benjy took to each other, and when Benjafield made the mistake of hinting that he’d like more speed, Moir decided to show him something, pelting him round Brooklands in his own short-chassis racer to show the nervous doctor what speed really meant. Later he claimed to have hated it. “I got out of the beastly thing knowing that never before had I been so utterly terrified.” But the high-spirited Moir persuaded him to buy it, and soon Benjafield was racing and winning; within a year Moir asked him to join the team for the ill-fated ’25 race.

Sadly, 1926 was another flop – Sammy Davis, driving No7 with Benjafield, crashed – but Benjafield bought the repaired car and entered it in the Boillot Cup at Boulogne. However, he hit a tree, later commenting: “I had come through a really bad smash with nothing worse than three broken ribs, four broken teeth and a crushed lip – a considerable source of embarrassment to me that evening…”

“I had come through a bad smash with nothing worse than broken ribs, broken teeth and a crushed lip”

However, he was cheered up in hospital by another of the Boys. He wasn’t terribly rich, but George Duller had a wealth of that other Bentley resource – fun. A cheeky humour and a fund of stories made Duller popular on an evening in town, but he maintained his seat on the unofficial Bentley ‘board’ because of his sportsmanship. Compact, fit and competitive, Duller’s other existence was as an amateur steeplechase jockey, an unusual parallel for a racing driver; yet he became very successful behind an engine. Perhaps hands that were sensitive to a horse’s bit could also gauge just how far to push a car.

That sense of fun showed when visiting the injured Benjy. “He was most sympathetic until he discovered my injuries were so trivial,” recalled the doctor. “As soon as he realised this he started his inimitable clowning to make me laugh. The result was not only painful but started my lip bleeding again.”

1926 was another dark year at Le Mans, when one 3-litre crashed and one broke a rocker arm; for a while it seemed that Benjy might triumph, until Sammy Davis went off.

WO Bentley did not plan to enter Le Mans in ’27; it was Benjafield’s pressure which made him relent. The doctor had spent a lot of money on ‘Old No7’ and was proposing it as a team car – customer dedication once again helping out the company. But the doctor wanted Sammy Davis as co-driver, and when Bentley announced that Davis would partner Clement on the new 4½, Benjafield wasn’t prepared to agree. “Strictly speaking, in the interests of the team I should have given way,” he wrote; but he held his ground.

This was the year of the notorious White House crash, when the works 3-litre and the new 4½ collided avoiding a spinner and Davis in Benjy’s old faithful managed to hit the pile up only lightly. Rough repairs got him going again, and when the leading Aries broke down, Davis and Benjafield were the winners. Benjafield showed his sportsmanship by pulling up 15 minutes before 4pm to let Sammy take the flag.

Hillstead recalled his thoughtfulness at Le Mans when the doctor discovered him hungry but tied to his post by lap-scoring duties; Benjafield soon reappeared with chicken and champagne. And when Bentley mechanic Billy Rockell was injured, Benjy got him into his own hospital, St Georges. He was the ideal mix of professional and joker: “Wonderful fun at all times,” recalled WO. “Except perhaps before a race. Benjy worried – a useful asset in a racing driver.”

“Benjy was fun, but he worried before a race – a useful asset in a racing driver”

Though he failed to finish in ’28, Benjy, with Baron André d’Erlanger, took third in the dominating 1-2-3-4 result at the Sarthe in ’29, a fine end to his Le Mans career. He died in 1969.

The Boys were all friends, but Benjy liked to drive with SCH Davis, Technical Editor of The Autocar. Davis was already a seasoned racer when Benjy invited him to share No7 Bentley at Le Mans in 1926, and his sterling recovery after the White House smash made him a bit of a hero even among the Boys. Admired equally for his racing and his journalism, Sammy received two BRDC Gold Stars, in ’29 and ’30. After a serious crash in 1931 he turned to rallies, continuing to write in The Autocar and many books. He died in 1981.

Benjafield’s racing successes in 1924 inspired a new, quicker ‘100mph’ model – and one purchaser wanted to go racing. He was called Woolf Barnato. Loud and self-indulgent, with a whiff of scandal attached, he had inherited millions from his diamond- dealer father. By early 1926 he had been persuaded to buy not only the new 6½-litre car but the firm as well, and suddenly the business, at that point facing liquidation, had proper financial resources.

‘Babe,’ as the husky six-foot athlete was known, based himself at Ardenrun, the vast house on his 1000-acre estate in Surrey. In 1929, celebrating his second Le Mans victory, he laid on charabancs to bring guests down from London for ‘the Grand Prix de Danse’, where there were impromptu races on the estate. He did not jump straight into the racing team, though; it was two years after buying the firm that he became one of the Boys.

Though brash, Barnato was anything but rash; he was shrewd, avoided unnecessary risk, and religiously followed WO’s racing orders. The entertainment was lavish, yet he had a name for petty parsimony and was a hard businessman. And while he revelled in the glory, he was just as dedicated while pounding round a sodden Montlhéry circuit chasing 24-hour records, with neither applause nor champagne in prospect.

His most famous exploit, beating the Blue Train in a dash from Cannes to London, has become a defining element in the Barnato story; yet far from being the spur of the moment bet of legend, it was carefully prepared and rather low key. Indeed he undertook it only to prove it was no great feat.

He was, said WO, “the best driver we ever had, and, I consider, the best British driver of his day”. If any of his victories showed his racing discipline in high contrast to the playboy image, it was in 1928. By now chairman of Bentley, he nevertheless took his orders from WO and accepted his place with Bernard Rubin in the third team car, the repaired ’27 winner. And after the Birkin/Chassagne Bentley was delayed by a puncture and the Clement/Benjafield chassis cracked, Barnato, sharing with Rubin, showed superb restraint to shadow the leading Stutz until it faltered, meanwhile nursing a car with a cracked frame and dry radiator to a tense win. It was his first Le Mans. With his wins in ’29 and ’30, he remains the only man to have won a hat-trick there from his debut.

He chose not to bale Bentley out of its debts before it was sold to Rolls-Royce during the depression of 1931, but his own fortunes survived. He died of cancer in 1948, aged 52.

WO had decided to stop racing after the 1926 debacle, but Barnato wasn’t going to miss that source of fun, and quickly put in place a renewed race organisation with a separate race shop. Part of the preparation for 1927 was to run a six-hour race at Brooklands in May, modelled closely on Le Mans. On probation was a new face, Captain Sir Henry Birkin.

Another war pilot seeking excitement, ‘Tim’ Birkin, being rich and vivacious, chose Bentleys. Small, slim, shy, with a slight stutter, he shouldn’t have been a hero; but with his dashy dress sense, pencil moustache and a fortune from Nottingham lace, he was an attractive character.

Perhaps due to what he had seen during WWI, there was a dark streak in the dapper baronet. He did take risks, he was not always an easy companion, and he had little sense of money. He soon spent his entire inheritance but failed to trim his lifesyle; he quarrelled with his partner in his garage business, and while his ghost-written racing memoir Full Throttle was a big success, he had signed away the royalties for previous debts. And he was tough on a car: WO called him “ruthless; I know of nobody who could tear up a piece of machinery so completely”. Still, he and French veteran Jean Chassagne took their 4½ to fifth in 1928, and the following year Tim partnered Babe in the winning car. However, while racing at the Nürburgring in 1928 he had been overly impressed by the supercharged Mercedes, and set out to build his own blown Bentleys.

On the social plane Tim fitted the Boys image completely, but on the track he was the maverick. In 1928’s Le Mans he drove too fast on a damaged tyre, stranding himself in a ditch for three hours. In 1930, though, he made the perfect hare to the hounds, running his own Blower at ferocious speeds and helping rid the team of its most feared rival by overstretching Caracciola’s Mercedes. Though no-one else believed the blower would finish, Tim did, and it was a sacrifice for him that it did indeed fail. As was turning to Alfa Romeo for a second Le Mans victory in 1931…

To his friend Benjafield’s distress, it was Tim’s careless attitude that finished him: neglecting dressings for his burnt arm led to Tim’s death from blood poisoning in 1933.

A late joiner, but quintessentially one of the Boys, Commander Glen Kidston joined the Le Mans team for 1929. Whereas many of the Boys had left the forces after WWI, he was still serving. A submarine officer, he loved shooting, hunted big game, boxed and raced motorcyles before the cars came along, and he had a record of drama. He was sunk aboard HMS Hogue in 1914, escaped from his sunken submarine, and had to smash his way out of a wrecked aircraft on a flight to Paris. A Riviera regular, he believed in Great Britain’s pre-eminent place in the world and wanted to prove her sons worthy of it. Motor racing was one arena for this, and sharing a Le Mans second place with Jack Dunfee in 1929, and winning with Barnato in 1930 helped make his point. He died in 1931 when his aircraft broke up flying over South Africa. Woolf Barnato wrote in his obituary that he was “a resourceful and gallant driver… the most perfect host… a good talker and a better listener… the beau ideal of a sportsman.”

“ ‘There was real joy,’ said sammy davis, ‘in the fact that one’s rivals were one’s friends’ ”

That, perhaps, is what caught the public eye about the Bentley Boys (a phrase which Benjafield, for one, disliked). It was more than success and wealth; sportsmanship was central to their friendly competitiveness. “There was real joy,” said Sammy Davis, “in the fact that one’s rivals were one’s friends.”

But with Bentley’s sale in 1931, the effects of the Depression and political shadows abroad, the light-hearted mix would not be repeated. “I question if we shall ever see again as cheery a crowd,” Tim Birkin wrote in 1932. “We were always seen together; we had the same manner of speech; the same jokes among ourselves.” He was partly right; racing drivers continue to have fun, but none since in such a visible, cohesive group as The Bentley Boys.

Taken from Motor Sport, February 2007