The eccentric racehorse owner at Hermits Wood

By Alison Bailey

When 35-year-old Dorothy Paget moved to Chalfont St Giles in 1940, she was one of the richest and most famous women in Britain. Widely known as Queen of the Turf, she invested a fortune in horse racing and owned the legendary Golden Miller. Famous for her eccentricities; she drove to the races at speeds of up to 100mph in a convey of Rolls Royces, always wearing the same old tweed coat for luck.

A larger-than-life character in every way, DP as she was known, was also reclusive and deeply private. She would hire out the entire Regent Cinema in Amersham when she wanted to see a film so that she could avoid sitting next to members of the public, particularly men who she was said to avoid at all costs. During the war she anonymously poured money into local charities such as the Red Cross and funded ambulances, a mobile canteen and children’s parties. 

The Honourable Dorothy Wyndham Paget (1905-1960)

Dorothy Paget was born 21 February 1905 in London, the second daughter of an English aristocrat, Almeric Paget, Lord Queensborough and his American heiress wife, Pauline Payne Whitney. The Pagets had recently moved from New York and lived at 39 Berkley Square, in great luxury thanks to Pauline inheriting a substantial share of the Whitney family fortune. Summers were spent in grand country mansions rented for the season or a large Arts & Crafts house near Newmarket which Almeric bought when he was elected Conservative MP for Cambridge in 1910.

Almeric Paget, educated at Harrow and Cambridge, had been sent to America to make his fortune which he did by marrying Pauline, 13 years his junior. Almeric and his father-in-law, William Collins Whitney, shared a love of racehorses and Whitney started to invest heavily, becoming the leading owner in the US in 1901. That year he also won the English Derby with Volodyovski.

The Whitneys were one of the most prominent breeding and horse racing families in America. DP’s cousin, John ‘Jock’ Hay Whitney, won the Cheltenham Gold Cup twice in 1929 and 1930 with Easter Hero. This is said to have prompted DP to buy Golden Miller and started her life-long rivalry with Jock who, from 1957-1961 served as Ambassador to the UK at the request of his friend and golf partner President Eisenhower.

Early life

Pauline completely spoilt her youngest daughter but perhaps this was because her distant father never hid his disappointment that she wasn’t a boy. Olive, the older sister by six years was being educated in France when 42-year-old Pauline died in 1916. Almeric immediately packed 11-year-old Dorothy off to boarding school.

Dorothy was expelled from six boarding schools before spending five happy years at a Parisien finishing school run by Russian émigré, Princess Mestchersky.  The Princess even reported back to her astonished father that she was an “exemplary pupil”. Here DP was moved by the plight of Russian refugees and built and funded a home which cared for hundreds of elderly Russians. A neighbouring street is called Rue Miss Paget in her honour. At the school DP first met Olga ‘Olili’ Mumm who became her lifelong friend and companion.

In Paris, DP also developed her talent for singing, taught by the famous teacher Madame Ciampi. When it was time for DP to return to London, she was accompanied by the Princess’s sister, Madame Orloff who remained with DP until her death as a paid companion. In London, DP continued with the singing lessons and is recorded as having made two public appearances “as a dramatic soprano of more than usual merit”. She performed at the American Women’s Club in London and in front of 500 inmates at Wormwood Scrubs!

A Debutante

In 1921, still desperate for a son, Almeric had made a second marriage to Edith Starr Miller, virtually half his age. Ironically the marriage produced three more daughters. A few years later it was this new stepmother who was tasked with organizing DP’s season as a debutante. Her elder sister was already married by 1919 and the family hoped to find a match for DP. However, she showed little inclination to find a husband and preferred gambling and playing cards at the parties she was required to attend.

By day DP’s favourite pursuits were tennis and hunting. She was an accomplished horse rider and rode in numerous horse shows and point-to-point races. Under 21 and not yet in control of her inheritance, she asked her father to finance her hunting in Leicestershire but when he refused a blazing row ensued which cause a lasting split in their relationship.

21 February 1926, DP came of age and inherited her half share of her mother’s fortune, which made her one of the richest women in Britain, and worth about £100 million pounds today. Her father sent her a Rolls-Royce as a conciliatory gift, which didn’t appear to do the trick as the next time they were seen together in public was when Golden Miller won the Grand National in 1934!

Dorothy, however, did socialise with Olive who had recently bought Leeds Castle with her second husband and was carrying out an extraordinary renovation project with her share of the inheritance. When Dorothy joined Olive for one of her legendary weekend parties, she slept in the Turret Bedroom. Other weekend guests included Winston Churchill, the Prince of Wales, Errol Flyn and Charlie Chaplin.

A passion for speed

After her inheritance DP was able to indulge her passion for hunting to the full. She rented a house, The Mote, close to Leeds Castle and kept five hunters there, riding side-saddle with the Mid-Kent Staghounds. After she stopped riding herself (probably due to gaining weight) she continued to take an interest in equestrian events. Her showjumpers, trained by Peggy ‘Pug’ Whitehead, competed at the highest level, often ridden by Pug or her daughter Sue Whitehead.

DP was passionate about speed in all its forms and loved owning and driving fast cars. The main requirement for a new secretary was that she was able to drive and was prepared to hare around the country lanes as fast as possible with no regard for the speed limit.

One of DP’s favourite cars was a fabulous, supercharged Rolls Royce 31HC much admired by the handsome and charismatic racing driver Sir Henry ‘Tim’ Birkin who gave her driving lessons at Brooklands in Surrey. He described her as one of the finest women drivers he had ever come across, “capable of handling any make of racing car produced in this country or abroad” and encouraged her to take part in races and hill climbs under the pseudonym Miss Wyndham.

In 1930 DP invested £40,000 in Birkin’s Bentley racing team, the equivalent of £2.5 million in 2025. She pulled out a year later to concentrate on horseracing, after the team failed to win a major race but she continued to support Birkin, and they remained close friends until his early death in 1933. Whilst DP only developed lasting relationships with women, her most recent biographers, Graham Sharpe and Declan Colley, believe that there was a genuine attachment between the pair. Birkin’s death had a profound effect on DP. Afterwards she lost interest in her appearance and started to eat excessively until she weighed more than 20 stone.  

Horse Racing and gambling

However, motor racing’s loss was definitely horse racing’s gain. DP invested heavily in the sport and in 1931, on the advice of her trainer Basil Briscoe, purchased a promising young National Hunt gelding named Golden Miller, and a good hurdler called Insurance. Arguably Golden Miller became one of the greatest jumpers of all time, winning five successive Cheltenham Gold Cups in the 1930s and the Cheltenham Gold Cup and the Grand National in 1934. He is still the only horse to win both in the same year. Insurance became a Champion Hurdler winning the coveted Cheltenham Festival Champion Hurdle twice in 1932 and 1933.

In 1936 DP acquired the Elsenham Stud Farm in Bishops Stortford, Essex where Straight Deal, who went on to win the Derby in 1943, was born. 10 years later she bought the Ballymacol Stud in Ireland where Straight Deal sired the 1957 Champion Hurdle winner, Merry Deal. In total, DP’s horses, racing under her blue and yellow colours, won 1,532 races on the flat and over jumps. She owned two more Cheltenham Gold winners, Roman Hackle in 1940 and Mont Tremblant in 1952. After her death, the British industrialist, Sir Michael Sobell bought most of her horses and the Ballymacoll stud, continuing her bloodline.

Chain-smoking and dressed in her lucky tweed coat and beret, DP was an intimidating presence on the racecourse. She was usually accompanied by an entourage of female companions, her racing secretary, Ruth Charlton and her close friend Sir Francis Cassel, her racing manager. However, he was never paid by DP and was as rich as she was. Her first biographer Quintin Gilbey described Cassel as “no more attracted to women than she was to men.”

DP invested millions of pounds in the sport whilst also indulging another passion – gambling and bet huge sums daily. When she wasn’t at the races, DP slept by day and gambled by night. William Hill employed night-time staff to take her calls and even allowed her to place bets on races that had already run. He trusted that she did not know the results and the fact that she lost more than she won proved her honesty.

The trainers

DP was a notoriously difficult owner and went through several horse trainers, often driving them to despair, with late-night phone calls demanding running plans and jockey changes. When one of her trainers, Frenchie Nicholson, unplugged his phone so he could get some uninterrupted sleep, she sent a secretary round to reconnect it! Basil Briscoe is supposed to have said: “Training horses is child’s play but it’s a hell of a bloody job trying to train Miss Paget.”

Whilst she could be domineering and even a bully, she was a generous tipper, usually giving her jockeys 21% of any winnings. She could also take a joke at her own expense. After a disappointing race on her horse Colonel Payne, she flew at jockey Gordon Richards to demand the whereabouts of trainer Fred Darling. Quintin Gilbey wrote: “on the ground, Gordon barely came up to her ample bosom but he fixed her with his steadfast brown eyes and replied, ‘I wouldn’t be quite sure Miss Paget, but I’ve a shrewd idea he’s on top of the stand cutting his throat’. This was a reply from DP’s own heart and though she had lost an astronomical sum she burst out laughing”. Fred Darling did not last much longer as her trainer, but Sir Gordon Richards became a lifelong friend and took over training her horses after his retirement as a jockey.  

Hermits Wood

DP lived in Chalfont St Giles for the last 20 years of her life although few of the local residents ever saw her. Hermits Wood was a 12-bedroom Arts & Crafts style mansion in 43 acres surrounded by high walls. It was demolished in 2006 and replaced by a development of luxury apartments, Ellwood Hall. To escape wartime London in 1940, DP initially rented the house from Sir Reginald Blair, a former Conservative MP and the chairman of the Racehorse Betting Control Board (later The Tote).

To some criticism, DP continued to race during the war, thinking the sport was critical for morale, and is credited with keeping the sport going through her continued investment. She also supported the Rickmansworth branch of the Women’s Voluntary Service with large donations and paid for soldiers’ cigarettes when they watched films at The Regent. 

After the war, she acquired neighbouring Pollards Wood Grange in six acres, which had been used as a training school for Polish SOE agents. It became extra staff accommodation for her growing number of assistants and secretaries as her unusual hours meant that staff often worked in shifts. For example, she employed two chief cooks, Mrs Hackemer to provide daytime meals and race picnics and Mrs Styche to supply nighttime meals.  

Contrary to many press reports who claimed that she hated all men and wouldn’t have them anywhere near her, the staff included a long-suffering butler, Robert, a chauffeur Harry Jackson and Mr Hall the gardener. His duties included mowing the lawn at night to avoid disturbing her sleep and standing out in Nightingales Lane to stop the traffic when DP’s convoy was setting off to the races.

It is said that DP always travelled in a convoy of at least two cars after suffering a puncture on the way to the races. She got one of her assistants to hail the first vehicle which was a passing and promptly bought it so she still could get to the races on time.

DP mainly lived upstairs and despite her great wealth, had no interest in the decoration or furnishings in the house. Whilst her sister, now Lady Baillie, was known for her art collection and lavish interiors, DP only bought furniture for its practicality and copies of the Racing Post were piled up everywhere. Her staff had to wait for her to be away at Wimbledon, another of her great passions, or on one of her regular trips to the theatre, before they could clear out her rooms and redecorate or replace carpets.

DP was reported to be a difficult woman to work for, not least for the unsociable hours she kept. Most of the communication with her secretaries was through memos, and all staff were colour coded, but her core staff lived with her for years and were fiercely loyal. She was capable of great kindness and paid for the children of her staff to be privately educated. She also threw lavish staff parties and gave generous thoughtful gifts to each member of the team at Christmas.

The final fence

DP’s unhealthy lifestyle and overeating led to her developing diabetes in her later years. 12 days before her 55th birthday, she died in her sleep after suffering a stroke. Her funeral took place 12 February 1960 at St Mary’s Church, Hertingfordbury where both her parents were buried. Truey Clarke, her chief mechanic and driving secretary, drove DP’s closest friends from Hermits Wood in the Jaguar at speeds up to 100 mph, which would have certainly met DP’s approval. The funeral procession included a string of her racehorses, and her coffin was draped with blue silk and covered with daffodils to represent her racing colours. The vicar was assisted by the Russian Orthodox Bishop of Sergieve and the Russian home in Paris sent an enormous wreath, more than three feet high. A heartbroken Olili died from cancer the following year.

Despite her lavish investments in horse racing and the eye watering amounts she lost gambling; DP left a fortune worth £85 million today (2025). As she died intestate, most of her money went to the UK treasury, with the residue inherited by her sister (a mere £17 million!).

Sources

The Famous and Infamous of the Chalfonts and District, DJ Kelly, 2014

The Dorothy Paget Story, Quintin Gilbey,1973

Dorothy Paget, the eccentric Queen of the Sport of Kings, Graham Sharpe and Declan Colley, 2017

Five Gold Cups, seven secretaries and a £250 meat van – the crazy world of Dorothy Paget

British Newspaper Archive

The Honourable Dorothy Paget (1905-1960), elsenham-history.co.uk