Money was a constant worry for both Winston and Jennie. Although Jennie had a life interest in the trust established by Randolph’s will, the income seldom reached the £800 annually required to pay Winston’s and Jack’s allowances. She had received nothing from her mother’s will,* her main income being £2000 a year from her marriage settlement. Nevertheless, after Randolph’s death, having tasted freedom during her fling in Paris with Bourke Cockran, she had no wish to return to living with the Dowager Duchess. And when she looked for a new house there was no sign of any financial retrenchment. She leased 35a Great Cumberland Place, a seven-floor mansion a block from Connaught Place, close to Hyde Park and Park Lane, and continued to live as though money was of no concern. She wrote to Winston in March 1897 that from her total annual income of £2700 (about £162,000 today) she provided the allowances of £400 a year each to him and Jack. Then there was over £400 for rent of the house and stables, leaving her only £1500 for everything else – taxes, servants, food, dress, travelling. In addition, she now had to pay interest on the money she borrowed.8 It is possible she worried about her finances in the dark hours of the night, but she never allowed this to impede her very full life at the apex of court society. Encompassing numerous flirtations and love affairs, her life went on almost as it always had, by virtue of raising loans and by accepting gifts from her many admirers and friends.
At the end of that year Jennie found that she needed £17,000 (today, £1.1 million) – more than six years’ income – in a hurry, in order to repay some fixed-term loans that were coming to an end and to satisfy those creditors who would wait no longer. Her solution was to insure her own and Winston’s life and use these life policies as guarantees against new loans. The drawback was that she needed Winston to guarantee the premiums of £700 a year, should she default, and she was fully aware that this would be an impossible sum for him to meet if it came to it. When Winston received her letter – the mail took two months between England and India – he felt he had little option but to agree. But he too had borrowed extensively:
Speaking quite frankly on the subject – there is no doubt that we are both, you and I, equally thoughtless – spendthrift and extravagant. We both know what is good – and we both like to have it. Arrangements for paying are left to the future. My extravagances are on a smaller scale than yours. I take no credit to myself in this matter as you have kept up the house & have had to maintain a position in London. At the same time we shall vy soon come to the end of our tether – unless a considerable change comes over our fortunes and dispositions. As long as I am dead sure and certain of an ultimate £1000 a year – I do not care as I could always make money on the press – and might marry. But at the same time there must be a limit…I sympathise with all your extravagances – even more than you do with mine – it seems just as suicidal to me when you spend £200 on a ball dress as it does to you when I purchase a new polo pony for £100. And yet I feel that you ought to have the dress and I the polo pony. The pinch of the whole matter is that we are damned poor.9
He also wrote to Jack and suggested that he should take on a share of the family financial burden when he left university, to which Jack agreed.* Winston thanked him, admitting to his brother that money was the only thing in life that really worried him – that is, his own extravagant tastes versus his ‘diminished resources’.10 Despite the diversions he mentions in his letters – which for his fellow officers endowed with adequate funding and being waited on hand and foot no doubt made life in India under the Raj an extremely pleasant one – Winston felt every hour that passed was an hour wasted. He constantly pressed Jennie to help him with introductions and push his name with her important friends. ‘I cannot believe,’ he wrote, ‘that with all the influential friends you possess and all those who would do something for me for my father’s sake…You really ought to leave no stone unturned…it is a little thing for you to ask and a smaller thing for those in authority to grant – but it means so much to me.’11 A few months in South Africa, he maintained, would inevitably lead to a few medals, which – in a year or two – he could put to good use: he would ‘beat my sword into an iron despatch box’, as he put it. Every letter he wrote at this time harped on the same theme: advancement – not glory for glory’s sake, but as his passport into the political arena.
Eventually Jennie complied – or so Winston thought* – by travelling to Egypt to tackle Lord Kitchener, the Commander-in-Chief of the army there, in person about Winston’s requests for transfer. In reality Jennie’s journey to Egypt was not solely to aid her son’s ambitions. By coincidence her latest lover Major Caryl Ramsden, regarded as the handsomest man in his regiment, the Seaforth Highlanders – an attribute for which he was nicknamed ‘Beauty Ramsden’ – had just been posted there.
Perhaps worn down by Jennie’s stream of letters (her close links to the Prince of Wales could not have harmed her petition, and she got friends in Parliament also to write on Winston’s behalf), Lord Kitchener at last agreed to put Winston’s name down for a posting to the Sudan. At the same time he advised that there were no immediate vacancies in the cavalry. So Winston was still left kicking his heels while he waited for this promise to bear fruit. While he waited he managed to find some action in skirmishes along the North West Frontier, an area that included the strategic Khyber Pass, the site of constant struggles between British forces and local warriors. He pulled every string he could to get himself attached as a special correspondent to the regiments involved there. In one battle, to his gratification, he received a mention in dispatches praising his courage and resolution: ‘He made himself useful at a critical moment,’ the report read. His CO forecast that ‘if he gets a chance [he] will have a VC or a DSO’. In fact it was held by many senior field officers that the only reason Winston did not get a VC was because he had made too many enemies among the staff because of his pushiness. To his mother he wrote that he was noticed less because of anything he had actually done in that skirmish than for having ridden a grey pony, thus making himself conspicuous among the brown ponies ridden by his fellow officers, chosen so as to provide a less obvious target for snipers. But the reports and diaries that covered this battle, and another that would follow, show that Winston was always in the front line, that he fought bravely and seemed heedless of his personal safety. In his letters to Pamela Plowden he happily recounted all the bullets that narrowly missed him.
Jennie’s love affair that winter came to an unexpected end. She and Caryl Ramsden parted tenderly before he rejoined his regiment in Wadi Halfa, and Jennie set off for England. When, on reaching Port Said, she was advised that her ship would be delayed for several days, she impulsively rushed back to Cairo hoping to spend a final few hours with Ramsden. On entering his hotel room unannounced, in order to surprise him, it was she who was surprised, for she discovered her lover in a compromising situation with Louisa, Lady Maxwell, wife of his commanding officer. The hotel was filled with interested British visitors who were subsequently treated to Jennie’s opinion of Ramsden at full volume. The story inevitably reached London and even the ears of the Prince of Wales. He, finding it amusing, wrote to Jennie reminding her: ‘You had better have stuck to your old friends than gone on your Expedition of the Nile! Old friends are best!’ Jennie was in fact deeply hurt by Ramsden’s betrayal, and when she received this note on her arrival in London she fired off a robust reply to the Prince, citing a similar thing that had happened to him. Fortunately her sister Leonie, having offered to post the note, wisely destroyed it. And later, when he understood how truly upset Jennie had been by the affair, the Prince would apologise: ‘I must ask your pardon if my letter pained. I had no idea que c’était une affaire si sérieuse [it was such a serious affair],’ he wrote.12
Jennie was a frequent guest at Sandringham and was always welcome at Marlborough House entertainments, which indicated that Princess Alexandra approved of her. Hostesses wishing to make up a house party to include the Prince often invited Jennie because she knew how
to charm and please him, in addition to whoever happened to be the maîtresse en titre of the moment. Photographs dated 1898 show Jennie sitting beside the Prince when he had his first drive in an early motor car. He regularly made informal late-afternoon calls at her home, when the servants were likely to be off duty after the ritual of tea and before that of dressing for dinner. By common consent this was the ‘safe time’ for a gentleman to call upon a mistress. Adultery was widespread among the upper classes because, as noted earlier, divorce was unacceptable – it would play havoc with the estates and money of those concerned. But provided the succession of an estate was secured, a discreet affair was regarded as a safe outlet for passions and boredom. The practice of afternoon visits was even given a code-name by the cognoscenti: the cinq à sept (the five-to-seven).
After Jennie’s death hundreds of letters and notes from the Prince were found among her papers. After Randolph’s death all these letters begin ‘Ma chère Amie’, but none was compromising – the Prince had obviously learned that lesson from his youthful experience with Lady Aylesford – and although there are some obvious coded phrases, they offer no evidence that the couple ever had a sexual liaison.13 Yet from what we know of Jennie’s attitude to men and from the historical evidence of the Prince’s serial womanising, it would have been uncharacteristic for them not to have slept together at some point. Also, it is known that in 1889 Randolph forcibly ejected the Prince after finding him alone with Jennie ‘unchaperoned’. So it is not unreasonable to conclude that Jennie and the Prince were at times sexually intimate.
The Prince would have been entitled to regard an affair with Jennie as ‘safe’ because she was known to have a number of lovers, most of them younger than herself. Indeed, during her lifetime she was rumoured to have slept with more than a hundred men, though one must make allowances for gossip and plain jealousy. During the twentieth century this figure seems to have escalated to two hundred, which seems a little excessive, but there was nevertheless a small squadron of men either recognised by her intimates to have been Jennie’s lovers, and/or about whom Jennie wrote to Leonie. Apart from those already mentioned – Charles Kinsky, Freddy Wolverton and others – among the rest were Hugh Warrender, Henry de Breteuil, Baron Hirsch, Kinkaid Smith, Paul Bourget, Sir Edgar Vincent, William Waldorf Astor, Lord Dunraven, Thomas Trafford, Norman Forbes-Robertson and Harry Cust. From her correspondence can be gleaned others whose full names are not given – someone called Simon, and another – an Italian – called Casati. Then there was John Delacour, whom Randolph intended to cite as corespondent if they were to divorce, and a number of men in Ireland who were written about but unnamed in her correspondence. And besides her lovers, Jennie seemed to be able to attract and impress men of power and character who never hopped into her bed, and these – Lord Salisbury, the Duke of Cambridge and Lord Cromer to name three – were all grist to Winston’s mill, contacts to be exploited to achieve his ends.
The question must be asked: Was Winston ever aware of his mother’s numerous lovers? The answer is unequivocally yes. An observant teenager, he once noted that when Jennie went out to lunch there was a tiny run in her stocking near the ankle; when she returned after tea the run had transferred to the other ankle. And in a letter to Jack when their father was in South Africa, Winston reported that while enjoying a rare exeat and instructed to stay with his grandmother he had gone home first to surprise his mother, to find her breakfasting with Charles Kinsky.14 He was sixteen, not so young that he could not guess what this implied. There is also the story that Winston once challenged a fellow officer to a duel after his mother’s reputation was called into question; but he must have been aware that she was something of a sexual predator. On one occasion, after reading a racy book entitled An Englishwoman’s Love Letters, he wrote to Jennie, ‘Are all mothers the same?’15 To Winston, though, whatever her faults, Jennie remained the perfect woman. Her early neglect of him seemed never to have affected his feelings for her; he was tolerant of her peccadilloes, and when he bullied and cajoled her that was simply part of his relationship with her – he loved her deeply. It is very probable that Winston’s chaste behaviour as a husband owed something to his disapproval of his mother in this one respect. But watching his father die slowly from a diagnosis of syphilis must also have been an object lesson.
Certainly, Jennie managed to stay friends with the Prince of Wales for the rest of her life, indicating a genuine affection between them that was more than simple lust. From the Prince’s view point, she was a friend of long standing who was discreet and who knew how to keep him entertained at boring parties. The relationship provided Jennie with a social cachet that few widows in her financial position could match and that ensured her a constant flow of invitations. She often spoke to the Prince about Winston; she mentioned such conversations in her letters to Winston and passed on short messages to him from the Prince.
When Winston published his first book, The Story of the Malakand Field Force which detailed the 1897 military campaign on the North West Frontier, he had been working against time, having learned that a fellow officer was also writing a book on the subject. Clearly, there was no market for both, and he knew his had to be published first. It was Jennie who found an editor and got the book out quickly. She presented a copy to the Prince and to top politicians, all of whom were complimentary about it, though Winston himself was in an agony of despair. Because of the time it took for the mails to get to India and back he had decided to forgo checking the proofs himself and asked an uncle* to read them for him. In the event the book contained dozens of typographical errors, and Winston feared this would reflect badly on his work. ‘I blame myself and myself alone for this act of folly and laziness,’ he wrote miserably to Jennie, ‘which has made me ridiculous to all whose good opinion I would have hoped for.’ But the editorial errors were overlooked; the book sold more than twelve thousand copies and provided him with some much needed income.
Meanwhile, he was hard at work on another book, to be called The River War: An Historical Account of the Reconquest of the Soudan. In a letter to his mother he made a self-revealing remark: ‘I think what is written is really good. Let me quote you one sentence – it is about the Mahdi [the Sunni Muslim leader] who was left while still quite young an orphan: “Solitary trees, if they grow at all, grow strong: and a boy deprived of a father’s care often develops, if he escape the perils of youth, an independence and a vigour of thought which may restore in after life the heavy loss of early days.”’16 One cannot help but wonder whether it dawned on Jennie that he was writing from personal experience.
It was Jennie who got Winston a regular column in the Daily Telegraph, though he considered she had not tried hard enough to get him the fees he thought his pieces were worth, and he was furious to find that he was being published over the byline ‘From a serving officer’ instead of ‘From Winston S. Churchill’. He welcomed the income, but he wanted his name put constantly before the British public; it was all part of his long-term plan.
At this point, in July 1898, Jennie received an invitation from Daisy Warwick* to spend a long weekend at Warwick Castle. Among the guests was a twenty-four-year-old Scots Guards officer, George Cornwallis-West,† a godson of the Prince. One of George’s sisters, Daisy, was married to Prince Heinrich of Pless, and the other, Shelagh, to Hugh Grosvenor, 2nd Duke of Westminster. The two girls were exceptionally attractive, and George was said to be ‘one of the handsomest men in England’. It was expected of George that he would marry as well as his sisters had done, since although the family owned two properties – a 10,000-acre estate at Ruthin in North Wales and Newlands Manor near Lymington, Hampshire – there was no money. George’s parents had been badly hit by the agricultural recession of the 1870s, and the Ruthin estate had been rented to tenants while the family lived between the smaller Newlands Manor and their London house. George knew all this but by his own account he took one look at forty-three-year-old Jennie – ‘Still beautiful,’ he recalled; ‘she d
id not look a day more than thirty, and her charm and vivacity were on a par with her youthful appearance’ – and fell headlong in love.17
Jennie’s initial interest in George is likely to have been that he was an exact contemporary of Winston’s, the two having been born within a fortnight of each other, so she was especially kind to the young officer. Over the weekend at Warwick Castle he took her boating on the river and she told him all about Winston. Thereafter, he bombarded her with notes, letters, gifts and declarations of love until she succumbed and, against her better judgement, fell in love with him. As we have seen, it was not unusual for men to fall in love with Jennie and some became her lovers, but although many of them were younger than Jennie, George was so much younger that the affair was bound to cause gossip, and it did. The Prince of Wales was soon writing to her rebuking her for being ‘up to your old game again…it is a pity you have got yourself so talked about – and remember you are not 25’.18
While Jennie was in the throes of this affair, Winston heard from the War Office that his long-awaited posting to the Sudan had been approved. Delighted, he packed hurriedly, anxious to catch a steamer about to depart. In his haste he left unpaid a small bar bill of 13 rupees at the Bangalore United Services Club. The amount was recorded in the club books as an ‘irrecoverable sum’ and is still proudly shown to visitors. Winston caught the steamer and reached Egypt just in time to participate in what is known as the last great cavalry charge at the Battle of Omdurman.* The Anglo-Egyptian forces, twenty-five thousand strong and led by Kitchener, had assumed this would be a mere skirmish with a few thousand men crouched in the scrubby bushes, which appeared as a large black smudge ahead of the British lines. As they rode towards the enemy, however, the ‘bushes’ turned into men, and immense numbers of tribesmen appeared over the crest to join them until Kitchener’s men found themselves facing a dense living wall four or five miles wide. It was the entire army – sixty thousand dervishes – of Khalifa, successor to the Madhi. And while Winston watched, amazed at the sight, a deafening wave of sound hit the British forces as the enemy host called on the Prophet for victory. Winston declared: ‘This is an hour to live…talk of fun…where will you beat this! They think they are going to win. We shall see about that…The masses…defined themselves into swarms of men, in ordered ranks bright with glittering weapons, and above them danced a multitude of gorgeous flags. We see for ourselves what the Crusaders saw…19
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