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Winston and Jack – The Churchill Brothers Presentation by Celia Lee

International Churchill Society Conference, Franklin, Tennessee

22 – 25 March 2018

Celia and John Lee are the authors of The Churchills. Purchase your copy here.

The current generations of Churchills were descended NOT via the male line but via the female line of John Churchill the 1st Duke and Sarah nee Jennings the 1st Duchess of Blenheim Palace.  John Churchill the 1st Duke earned fame and renown, having fought at the Battle of Blenheim in 1704.  The only son of John and Sarah’s marriage died, and their second surviving daughter, Henrietta, at her father’s death, was allowed to take the title of 2nd Duchess of Marlborough. At her death, the title then passed to the family of her sister Anne Churchill, who was married to Charles Spencer, and it is from this matrilineal Churchill/Spencer line, that the present-day Spencer-Churchills are descended.  Anne had pre-deceased Henrietta but Anne’s second, surviving son, Charles Spencer (1706 – 1758), became the 3rd Duke Of Marlborough, hence the name being altered to Spencer-Churchill.  The late Diana, Princess of Wales, whose maiden name was Spencer was descended from the same family line.

The modern Churchill family tree shows at the top, John Winston Spencer-Churchill the 7th Duke of Marlborough of Blenheim Palace, and his wife, Frances nee Vane the 7th Duchess, who was the daughter of Lord and Lady Londonderry.  The Duke and Duchess produced eight, living children, two of whom were sons.  Their first son was George, who would inherit the title of the 8th Duke.  Their second son was Lord Randolph Spencer-Churchill. Lord Randolph married an American, Jennie Jerome, and they are the parents of the late Sir Winston Churchill and his brother John, known in the family as Jack.

Sir Winston Churchill dropped Spencer from his surname, because as a boy, attending Harrow Public School, when the boys were lined up for an event, he was last, due to ‘S’ being so far down the alphabet.  Spencer however, remains officially part of their surname.  The late Diana, Princess of Wales (nee Diana Spencer) was descended from the same line, and there was an earlier Lady Diana Spencer, born 1710 who also died young, aged only 25, in 1735.

Politics dominated the Churchills’ lives. The Duke of Marlborough who was Lord Randolph Churchill’s father was sent to Ireland as Viceroy, that is Queen Victoria’s representative, from December 1876, until the spring of 1880. The Duke and Duchess lived in the Viceregal Lodge, Phoenix Park, Dublin.  Lord Randolph, Jennie, little Winston aged 2 years, and his nanny, Mrs Elizabeth Everest, lived in the White Lodge in the grounds.  Lord Randolph who was  Conservative member of Parliament for Woodstock, Oxfordshire, took up the position of unpaid secretary to his father. Dublin Castle was the seat of British rule in Ireland and was used also for political meetings and banquets.

It was whilst they were in Ireland, that Lord Randolph went through a metamorphosis in political thinking that would alter the Churchills lives for generations to come. The spark that lit the flame that brought about this change in his formerly quiet personality, lay in what the Churchills found in terms of poverty and squalor, amongst the Irish peasants and working classes, that shocked and horrified them.

Disaster threatened, when it poured with rain for months, and the potato and corn crops were lost and there was no seed for future planting.  Fear of famine like the one of 1845-9, when one million people perished, and a further million emigrated, now swept the land.

Heaped on top of that was the Nationalist Movement for an independent Ireland, agitation to break away from the United Kingdom of Great Britain and Ireland, the leader of which was Charles Stewart Parnell.

Lord Randolph persuaded the government to set up a small commission, on which sat he, and the expert on Irish affairs, Lord Justice Gerald FitzGibbon, the Law Adviser at Dublin Castle, and they enquired into the condition, management, and revenues of Ireland’s schools.

Together, Lord Randolph and Jennie travelled the entire thirty-two counties of Ireland to assess the situation. The Duchess of Marlborough assisted by Jennie set up a Famine Relief Fund, with Lord Randolph as its secretary.  Its purpose was to provide food, clothing, fuel for the fires, and small sums of money to keep able-bodied men, temporarily in distress, out of the workhouse.  Grants were made available to schools that they might provide meals for the children. Queen Victoria, the Prince of Wales, and all the great families of the mainland donated money, and the fun raised over £135,000 pounds sterling, today’s equivalent of over US$21million.  It was this reformist and humanitarian policy that would later influence greatly, Winston Churchill, when he became a Member of Parliament.

In Dublin, Lord Randolph used to sneak into the political meetings of Charles Stuart Parnell, and there he discovered a very different kind of political oratory.  These powerful, Irish speakers could shout and bang their fists on the table and be heard in a packed hall of hundreds, and at street meetings of thousands, and they knew how to rouse a crowd to their cause. As they were speaking in Irish, he understood only the odd word here and there, that he would have learnt from Fitzgibbon. One night he was recognised and got kicked out of the meeting.

Lord Randolph travelled back and forth to attend to his ministerial duties at the House of Commons in London, and the leading issue of the day was the Irish Question.  The years he spent in Ireland, turned him into an expert on Irish Affairs, and he was recognised as such.

In the midst of all this, Jennie gave birth to another son, on February 4, 1880, named John Strange, known as Jack.  Later that year, the Duke of Marlborough’s term as Viceroy came to an end, and both families returned to live in England.

Now we come to Winston and Jack as school boys. A comparison between the brothers shows that Winston was ever in trouble. Her performed poorly as an academic and failed the entrance exam for Harrow Public School. The Headmaster took him in, due to the high political status of his father whom he admired.

In contrast, Jack who was over five years younger, was by far the clever of the two brothers.  A visitor to the Churchills’ home one day asked Jack if he was ‘a good boy’ to which he replied, ‘Yes, but brother is teaching me to be naughty’.  At age seven, Jack was sent to Elstree preparatory boarding school, and unlike Winston, he took to learning like a duck to water.  He was mostly at or near the top of his class. He took the entrance examination for Harrow public school a year early and passed. Throughout his entire education, he was never once punished and was a model pupil.  He of course expected rewards for being good and a typical letter home read: ‘I have been top of my form three times’, and he wanted more money, food hampers, sweets, more visits from his mother and the nanny Mrs Everest, and he would demand: ‘Bring me a hamper and two tins of sardines’.  The letters from both brothers to their fathers, however, were more to do with which horse won which race, and how much were the family’s earnings from the winnings. Being the sons of ‘The coming man’ in politics meant that both boys were looked up to at school and they made extra pocket money by cutting out their father’s signatures form his letters and selling them to their classmates.

Winston and Jack grew up as part of a family that was obsessed with politics.  Randolph and Jennie frequently entertained other Members of Parliament to lunch at their home, and 12-year-old Winston would sit amongst them at the table, where he learnt political debate.  Another force, however, had prior claim over the Churchill brothers from their earliest years – the huge wall-to-wall tapestries at Blenheim Palace, espousing the fame of their illustrious ancestor, John Churchill, and his triumph at the Battle of Blenheim.  Initially, both boys wanted to become full-time soldiers and had collections of model soldiers that were added to each Christmas by parents and relatives.  Winston possessed an entire modern army, but he allowed Jack only coloured troops and no artillery. Their father having made both boys superb horsemen, entered Jack’s name into an army class at school. He arranged for him to meet Lord Roberts, Commander-in-Chief of the British Army, in the Head Master’s House at Harrow School.

Lord Randolph was fiercely popular with the people and he fought the old guard in the Tory Party, eventually becoming Secretary of State for India in a Conservative Government, and later, Leader of the House of Commons and Chancellor of the Exchequer.  If fate had not decreed otherwise, his next step would have been into No.10 Downing Street as Prime Minister. When Lord Randolph felt obliged to resign as Chancellor, having refused to make swingeing cuts, a messenger was sent to the Churchills’ house who asked to buy his robes for his replacement. Farsighted Jennie answered the request with: ‘No! I am preserving them for my son’ – meaning Winston!

Lord Randolph approached the Duke of Cambridge, formerly Commander-in-Chief of the British Army, asking that both his sons’ names be put down for the elite 60th Rifles of which the Duke was Colonel-in-Chief.

In 1894, Lord Randolph was struck down by a fatal illness and died on 24th January 1895.  Winston was then approaching his 21st birthday and was an officer cadet at Sandhurst Royal Military School.

That autumn, Winston took leave of absence and went to the Americas to observe the Spanish army in its campaign against rebels in the Cuban War of Independence.  Jennie was a friend of Democratic Congressman, Bourke Cockran, and he met Winston at the harbour and welcomed him to his home at 5th Avenue, New York, where he treated him to big cigars and fine wine.  Cockran would become a kind of father figure in Winston’s life, advising him on books to read from his large library, and he took him to West Point where he was ‘greeted like a general’.

Winston and his companion, Reggie Barnes, then set out to Cuba as observers Winston in the role of journalist for the London Daily Graphic.  On his 21st birthday he was in the thick of the fighting, following General Valdez, leader of the Spanish army, who was at Sancti Spiritus.  Three days later, whilst they were all bathing in a river a volley of shots rang out that went whistling over Winston’s and Barnes’ heads and it was, according to Winston, a near thing!

After Winston’s return to England, Jennie, encouraged by Bourke Cockran, hatched a plan with Winston, that he should serve in the army for a spell and make a name for himself, and then go into politics.  Winston passed out well from Sandhurst and joined the 4th Hussars and went with them to India.  But he found it all to be a complete bore and a waste of time and returned home.

Jack had been Lord Randolph’s favourite and now that he was dead, there was no one to fight Jack’s corner.  In his final days at Harrow School, aged seventten in 1897, the Headmaster Dr Welldon was making plans for him to enter Oxford University to study for a degree.

Now we come to the big obstacle of money!  In his will, Lord Randolph had left sufficient to provide for his wife and sons.  When Jennie was a child, living in New York in the late 1850s, her father, Leonard Jerome was reputed to be worth $10million about $500 million in today’s value.  She had been raised in fabulous wealth and luxury, and in adulthood, she didn’t understand the value of money.  She soon squandered the money on herself, and provided large handouts to Winton, who was often getting int det.  She insisted she cold afford to put only one son through an army career, meaning Winston.  She sent Jack to France for a year to learn French and he really applied himself to the subject and became fluent.

Jennie knew Ernest Cassel who was a stockbroker that handled the Prince of Wales (later King Edward VII’s) investments and who was nicknamed ‘the King’s banker’.  She took Jack to stay at the Prince’s country estate, Sandringham, Norfolk, where she introduced him to Cassel.  As Jennie’s father, Leonard Jerome had been a speculator on the American stock market, she got it into her head, that Jack should become a stockbroker and as she put it ‘make million’ for the family.  Winston put up fierce opposition, but she over-ruled him saying ‘I know best’ and she didn’t want either of her sons ‘risking your necks in the army’.

In January 1898, just three years after her husband’s death, Jennie made it known to her sons that she had to find £17,000 pounds sterling to buy up all the loans she had taken out. She wanted Winston to guarantee £700 per annum to pay the interest on her loans, and Jack was cajoled into agreeing to pay half of this sum.

Just prior to taking up his appointment with Cassel, towards the end of January 1898, Jennie allowed Jack to satisfy his interest in the army by joining the Oxfordshire Hussars, a part-time Yeomanry Regiment. After a month’s training, he could balance the two pursuits, working in the City for Cassel during the week, and joining his regiment at weekends.  He was promoted up through the officer ranks from 2nd Lieutenant to Lieutenant to Captain and then to Major.

The City of London in those days was not considered to be a fit place for a gentleman, still less the grandson of the Duke and Duchess of Marlborough. There existed an aristocratic disdain of those engaging in ‘trade’. Jack applied to join the Jockey Club and was turned down as they accepted only those engaged in gentlemanly pursuits and stockbroking did not meet that criteria.  As it turned out, Jack was for years only Cassel’s clerk and secretary, having had to learn shorthand and typing. He worked long hours in the claustrophobic heat of a city office, organising Cassel’s business meetings, and taking down minutes.  His son Peregrine who asked me to write a new biography of the Churchill family told me that he suspected that his father had not in the beginning been paid a salary and that had it had been forfeited in instalment payments to Cassel for a loan he had given Jennie. He also told me that when his father died he was the executer of his will, and he discovered that for years his father had been paying off Jennie’s debts despite her having died in 1922, and there was still in 1947, £80 owing and he paid it.

Cassel was heavily involved in the Aswan Dam project and when he went out to Egypt in January 1899, Jack accompanied him.  He wrote a series of letters to his mother of his misery.  Passing through Vienna on a train in the dead of winter he said: ‘We have just been through field after field of deep snow and it is freezing here.’ In contrast, they arrived in the sweltering heat of Cairo for the laying of the foundation stone for the Barrage Ceremony of the Aswan Dam.  Writing again to his mother, he told her he saw articles about her in the fashionable magazines of the day, saying how she was enjoying herself at balls.  In contrast, ‘There is nobody here of interest’.  Cassel gave a large dinner for thirty people and Jack had to arrange it.  Later at Cassel’s Daira Company, Jack wrote: ‘I have been all day in a factory with a temperature of over 100 degrees.’  His birthday had come and gone whilst he was there, and she had forgot it.

Winston went out as a war correspondent to cover in the Boer War in South Africa, (1899-1902), and was soon captured.  His sensational escape and subsequent life on the run, wanted – dead or alive – made his reputation. He then joined the South African Light Horse where he met up with Jack, who was commissioned as a Lieutenant and Troop Commander, 1st February 1900.  Jack was wounded in the ankle in his first action on February 11th and was the first officer casualty to be treated on the hospital ship Maine. There, he was greeted by his mother, who had been the driving force behind raising the money for the fitting out of this former, cattle-ship, and who had travelled on it in the role of administrator. Jack returned from his injury to active duty with his regiment, and served in Natal under Sir Redvers Buller, where he saw months of gruelling anti-guerilla operations, punctuated by some sharp battles, in which he conducted himself with noble gallantry.

Having served during the war, while publishing articles in the newspapers, Winston now returned to England a war hero ripe for politics and stood for the Conservative seat of Oldham in Lancashire. For many years, Jennie had learnt politics alongside Lord Randolph, and when he stood at election time she had campaigned for him in public. She now joined Winston and advised him how to make speeches and capture Oldham.

Jack left South Africa in late October 1900, when the war was thought to be near its end, returning home with the ringing endorsement of his colonel, Julian Byng. During his absence his mother had remarried, Lieutenant George Cornwallis-West who was the same age as Winston, both having been born in 1874. Jack complained to his mother, ‘I have to return to that horrid city’.

Winston was elected to Parliament,1st  October 1901, and was now set on a long political career that would be rocky to say the least. Jennie was for the rest of her life, the driving force behind Winston.  He could continue form where his father left off six years earlier, taking up his powers of oratory on the public platform and in in parliament, even to the to the extent of copying how he had worn his hat.  Perfecting his use of the English language, he fought everyone who stood in his way.  It was this inherited combination of powerful oratory and reformist policies, that was the glue that held Winston Churchill’s politics together and set him apart form other politicians.  When, in 1904, he famously crossed the floor of the House of Commons to join the Liberal Party, he would pursue reforms that alleviated the working classes, introducing factory tea-breaks, and planning the embryonic Welfare State. When he was wartime Prime Minister, he said in a Radio broadcast, 21st March 1943: ‘There is no finer investment for any community, than putting milk into babies.’

In 1906, Jack had became a partner in Nelke Phillips. For much of the rest of his life, he would sort out the Churchills finances, investing their money wisely for them, and he and Winston tried to stop their mother squandering her money at the gambling tables in Paris.

When the First World War broke out 1914-18, Jack immediately joined his regiment the Oxfordshire Hussars, and went first to Flanders on the Western Front, serving with distinction at a crucial stage in the First Battle of Ypres. Thereafter, his command of the French language saw him appointed to British General Headquarters in France.  He was able to keep Winston fully informed of the army’s progress in their constant stream of letters.

As Jack was one of the few staff officers with immediate practical experience of combat, General Sir Ian Hamilton asked for him to serve on his staff, when leaving for the Gallipoli expedition in March 1915. He served throughout the campaign as the Camp Commandant, General Headquarters, a vital posting, that ensured the headquarters functioned at peak efficiency for the duration of the campaign. Hamilton was recalled in October, but Jack remained in post until January 1916, when the last troops were evacuated to Egypt. He then returned to the Western Front and joined the staff of the 1st Australian and New Zealand Army Corps the ‘Anzacs’ and served with them throughout the fighting from 1916 to 1918. In 1917, he was able to give Winston a guided tour over some of the recent battlefields.  He ended the war as Military Secretary to the Fifth Army, and came home in 1919, with a Distinguished Service Order in recognition of his particular service in liaising with the French Army.

Jack returned to the city as a stockbroker, and, in 1921, was made a partner in Vickers da Costa. He was especially useful to Winston during the great upheavals of the late 1920s and early 1930s. In 1929, he accompanied Winston on a three-month tour of North America. The Great Crash occurred while they were there, and Jack was busy thereafter, supervising the retrenchments necessary in Winston’s normally extravagant lifestyle. He also managed the family’s tax affairs and was able to direct their investments into some very far-sighted and successful areas, including copper and gold mining, Marks and Spencer, and Gaumont British Films.

Throughout the Second World War, Jack was helping Winston in the underground bunker that is today the Cabinet War Rooms in London, whilst continuing to hold down his full-time job in the city. He organised a staff canteen at Downing Street that greatly improved the productivity of Winston’s immediate staff.  Amongst Jack’s papers I found pre-prepared letter-heads that bore Winston’s stamped signature, and Peregrine explained to me that his father had acted as a kind of extra secretary to Winston during the war.

In the years ahead, Jack would sink into obscurity to the extent that few people knew he ever existed. A whisper circulated, and several modern authors have claimed he was not Churchill at all and had been fathered by any one of about half a dozen men. As he was born in Dublin the majority of these men never set foot in Ireland.  When I was called in by Jack’s younger son peregrine to write a new family history, I was able to tell from old photographs that Peregrine bore a strong resemblance to the 7th Duke of Marlborough. He also bore a resemblance to Winston and his elder brother Johnny, even more so. It was apparent to me he was Churchill through and through.

Winston would emerge as the nation’s hero, credited with winning the Second World War. Jack did not survive to share in the glory of his brother’s triumph.  He had developed a tumour at his heart and died on February 22, 1947, a few days after his 67th birthday.


During the early stages of researching and writing the book, Roy Jenkins published his biography titled CHURCHILL.  He alleged that Jack had been fathered by John Strange Jocelyn the 5th Earl of Roden, that is still today a title in Northern Ireland. Peregrine and I checked out Jocelyn’s movements, and he did not arrive in Ulster at his Tullymore estate until shortly before Jack was born. The visitors’ book has survived, and present Earl of Roden advised us that Jocelyn signed in on 13th January 1880. The reason that Jocelyn (along with another half dozen or so names) has been cited by several authors as Jack’s paternal father has been that previous authors believed he lived in the estate in County Down when, in fact, he had only just inherited it from his nephew who had died of tuberculosis in Paris.  Jocelyn was a respectable married man who lived in England with his wife and two daughters, and he had not been to Ireland from he was a boy.  Another reason is that he was Jack’s godfather.  Jocelyn was on his return journey home to catch the boat from Dublin to England and called off to spend a day or two with his friend the 7th Duke of Marlborough. He was staying at the Viceregal Lodge when Jennie went into labour in the early hours of the morning, and he was roused from his bed to stand sponsor, Jack was a blue baby and the doctor thought he might not live so baptism took place right away. Jocelyn was then 56 years of age and Jennie was only 26 so they were an unlikely match in any event.

Peregrine was nearing 90 years of age and was not in the best of health and Jenkins’ book upset him terribly.  He felt that gossip was now rife in the country that he was not Churchill.  He told me one day that he would prove his identity for his grandfather Lord Randolph who is buried at St Martin’s Churchyard, Bladon, Oxford would have the same DNA.  ‘I will dig him up’, Peregrine told me, and rolling up his sleeve to show his arm, he continued: ‘I’ll have his DNA tested against mine.’

Peregrine and his wife Yvonne lived at Fairdown House, Hampshire, and I rang up one Monday morning to speak to Peregrine about something to do with the book. A neighbour answered the ‘phone and told me he had died suddenly in the early hours of the morning from a burst appendicitis. Tragically, he did not live to see his father’s and his own name reinstated as being legitimately Churchill.

When John and I visited after the funeral, Yvonne was still in shock and she blamed Jenkins’ book for killing her husband. She said to me: ‘Peregrine upset himself so much about it he made himself ill.’

In the next few months, Yvonne sold the house and moved back to London to near where they used to live and set up in a luxury flat off Sloane Avenue.  Somewhat ironically, when I switched on Sky News one night in 2003 the headlines were that Jenkins had died suddenly!  ‘Good’, said Yvonne when I rang her and told her, ‘Now we can print what we like’!

For the next several years, I visited Yvonne every month, and we discussed the progress of the book. It went to print without my telling her as I wanted to give her a surprise.  The official publication date of WINSTON & JACK THE CHURCHILL BROTHERS, a private edition printed especially for Yvonne, was 25th October 2007, and John and I went to visit her a few days before the official publication date, taking her an early copy.

When we walked into the drawing room, Yvonne began immediately telling us that a ghost was in her bedroom in the early hours of that morning.  She showed me the room and told me she awoke and saw him walking up and down the room past her bed. She said she knew is was Peregrine and she had always hoped he would come back but she wondered why he came now.

We took the book out of the bag and handed it to her!  ‘There’, she said, ‘That’s why Peregrine came back.  He knows the book is printed and the truth about his father is finally told. He will be happy now.’

I never did believe is ghosts and spoofs and the like, but I am always mindful of the utterance of William Shakespeare’s character Hamlet: ‘There are more things in heaven and earth, Horatio, than are dreamt of in your philosophy.’

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