The compelling letters between Winston Churchill and his mother Jennie

All through his youth, Winston Churchill bombarded his American mother Jennie with affectionate letters and requests for money.

He was far less close to his father, Lord Randolph, who, easily irritated, found Winston lazy, slipshod and careless. On Saturday, we published extracts from a new collection of letters, edited by historian DAVID LOUGH, from Churchill to his mother when he was at Harrow School.

Today, the missives continue as he marches to war . . .

March 27, 1892, Harrow School [aged 17]

My darling Mamma,

I’m ‘stoney’.If you could replenish the exchequer it would indeed be Tara-ra boom-de-ay.

May, Banstead [a rented house in Suffolk]

Dearest Winston,

Here is a P.O.O.for 30/- [£180 in today’s money]. Yr wants are many — & you seem a perfect sieve as regard [sic] money.

September 24, Invermark, Brechin [a friend’s estate in Scotland]

Dearest Winston,

I do hope you mean to work hard — I was rather chaffed here as to yr having been ‘ploughed’ [Winston had failed the entrance exam for Sandhurst].I suppose I made too much fuss over you & made you out a sort of paragon. However it will be all right if you put yr shoulder to the wheel this time.

The following summer, while Jennie took the ailing Randolph to two German spa resorts, Winston was sent off to tour Europe with an Eton schoolmaster.Just before leaving England, he learned he’d passed the Sandhurst exam on his third attempt — but that his marks were too low to join the infantry and he’d have to join the cavalry instead.

Churchill bombarded his mother Jennie with affectionate letters and requests for money

Churchill bombarded his mother Jennie with affectionate letters and requests for money

August 7, 1893 Bad Kissingen [spa in Bavaria]

Dearest Winston,

I am glad of course that you have got into Sandhurst but Papa is not very pleased at yr getting in by the skin of yr teeth & missing the Infantry by 18 marks.He is not as pleased over yr exploits as you seem to be! We are doing the cure most conscientiously & I think it will do Papa a lot of good.

September 17, Sandhurst

My dear Mamma,

I am awfully sorry that Papa does not approve of my letters.

I take a great deal of pains over them & often re-write entire pages. If I write a descriptive account of my life here, I receive a hint from you that my style is too sententious & stilted. If on the other hand I write a plain and excessively simple letter — it is put down as slovenly.

I never can do anything right. It is a great pleasure to me to write to you unreservedly instead of having to pick & choose my words and information.

March 16, 1894

My dear Mamma

I am awfully hard up and wish you would send me a sovereign, as I am reduced to almost bankruptcy.

March 17, 50 Grosvenor Square

Dearest Winston,

I am not going to read you a lecture as I have not time — but I must say you are spending too much money — & you know it.You owe me £2 [today £247] & you want more besides. You really must not go on like this . . .

By that spring, Randolph’s health had severely declined. Although he was being treated for late-stage syphilis, modern medical opinion is that he may in fact have been suffering from a different disease.To avoid the children witnessing the final stages, Jennie took her husband on a trip around the world.

September 15

My dearest darling Mummy,

I have not been more extravagant than before you went away, but rather less.The consequence of this has been that I ‘mortgaged’ my allowance for the next month and have had to pawn several of the things I used least. If therefore as the 30th Nov [Winston’s birthday] approaches or Christmas draws near you feel as if you would like to commemorate both or either of these auspicious birthdays -— a chequelet would above all things fill my heart with joy and gratitude.

November 2

My dearest Mamma,

I persuaded Dr Roose [family doctor] to tell exactly how Papa was — as I thought it was only right that I should know exactly how he was progressing.Dr Roose told me everything and showed me the medical reports.

I need not tell you how anxious I am. I had never realized how ill Papa had been and had never until now believed that there was anything serious the matter. Do, my darling mamma when you write let me know exactly what you think.

Winston passed out of Sandhurst in December, becoming a subaltern with the 4th Hussars.His father died the following month; there is no correspondence between mother and son about his death.

April 27, 1895, Aldershot

My dearest Mamma,

I am at present very hard up.Would it be possible and convenient to you to pay at present so large a sum as £100-£120? [£12,500-£15,000] It is an awful bore riding other people’s horses. The sooner the better — as ponies rise in price every day — and also I cannot go on without any for more than a few days — unless I give up the game [polo], which would be dreadful.

By August, Winston had been with his regiment for six months.He was already chafing at the routine of Army life, and beginning to think of a career in politics.

Winston Churchill's American mother Jennie Jerome Churchill whom he bombarded with letters

Winston Churchill’s American mother Jennie Jerome Churchill whom he bombarded with letters

August 16, Aldershot

My dearest Mummy,

It is a fine game to play — the game of politics.The more I see of soldiering — the more I like it — but the more I feel convinced that it is not my métier. Well, we shall see — my dearest Mamma.

In September the following year, Winston left for India with the 4th Hussars.

December 23, 1896 Continental Hotel, Calcutta

My dearest Mamma,

Calcutta is very full of supremely uninteresting people …and at night with a grey fog and cold wind — it almost allows one to imagine that it is London.

Bored and short of cash, Winston now wanted to return to London for a break.

February 26, 1897, 35a Great Cumberland Place, London [Jennie had bought a new house]

Dearest Winston,

If you cannot live on yr allowance from me & yr pay you will have to leave the 4th Hussars.

I cannot increase yr allowance. As for yr wild talk & scheme of coming home for a month, it is absolutely out of the question, not only on account of money, but for the sake of yr reputation. They will say & with some reason that you can’t stick to anything. You have only been out 6 months.

There is plenty for you to do in India.

I confess I am quite disheartened about you. You seem to have no real purpose in life & won’t realize at the age of 22 that for a man life means work, & hard work if you mean to succeed.

Jennie claimed to be too broke to give Winston a higher allowance.In fact, she had an annual income of £5,000 — £618,000 in today’s money — though she lied to both her sons, telling them it was half that amount.

March 5

Dearest Winston,

If you only told me when you were hard up — & why — perhaps I shld not be so angry.But I don’t believe you ever know how you stand with yr account at the Bank. I marvel at their allowing you to overdraw as you do. I do wish you wld try & reform — if you only realised how little I have.

March 17, Bangalore

My dearest Mamma,

I was only £45 [£5,560] overdrawn. It was very kind of you to pay it.

In September, Winston — accredited as a newspaper correspondent — travelled to India’s North-West Frontier, where the Army was trying to suppress a rebellion.

A young Winston Churchill in his school uniform. He would go on to be Prime Minister of UK

A young Winston Churchill in his school uniform.He would go on to be Prime Minister of UK

Sept 19, 1897, Camp Inayat Kila

Dearest Mamma,

I must give you some account of my personal experiences on the 16th.I started with the Cavalry and saw the first shot fired. After half an hour’s skirmishing I rode forward with the 35th Sikhs until firing got so hot that my grey pony was unsafe. I proceeded on foot.

When the retirement began I remained till the last and here I was perhaps very near my end.I was close to [two] officers when they were hit almost simultaneously and fired my revolver at a man at 30 yards who tried to cut up poor Hughes’ body.

The enemy came to within 40 yards [we were] firing our revolvers. I felt no excitement and very little fear.

At any rate whatever I do afterwards, no one can say anything against me on this score.I rode on my grey pony all along the skirmish line where everyone else was lying down in cover. Foolish perhaps but I play for high stakes and given an audience there is no act too daring or too noble.

I will write again soon if all goes well, if not you know my life has been a pleasant one, quality not quantity is after all what we should strive for.Still I should like to come back and wear my medals at some big dinner.

December 22

My dearest Mamma,

A fortnight from today I shall send you The Story Of The Malakand Field Force, An Episode Of Frontier War, by Winston S.Churchill. I hope you will like it. I am pleased with it chiefly because I have discovered a great power of application which I did not think I possessed.

To ride a grey pony along a skirmish line is not a common experience.But I had to play for high stakes and have been lucky to win. Bullets — to a philosopher my dear Mamma — are not worth considering. Besides I am so conceited I do not believe the Gods would create so potent a being as myself for so prosaic an ending.

‘Fame’ sneered at, melodramatized, degraded, is still the finest thing on earth.I shall devote my life to the preservation of this great Empire and to trying to maintain the progress of the English people. Nor shall anyone be able to say that vulgar consideration of personal safety ever influenced me.

I am not blind to the tawdry and dismal side of my character but if there is one situation in which I do not feel ashamed of myself it is in the field.

Sir Winston Churchill wearing a fine array of decorations photographed at review in Hyde Park

Sir Winston Churchill wearing a fine array of decorations photographed at review in Hyde Park

January 26, 1898

My dearest Mamma,

The publication of [my] book will be certainly the most noteworthy act of my life.Up to date (of course). By its reception — I shall measure the chances of my possible success in the world.

In Politics a man, I take it, gets on not so much by what he does, as by what he is. It is not so much a question of brains as of character & originality.It is for these reasons that I am somewhat impatient of advice as to my beginning in politics. Introduction — connections — powerful friends — a name — good advice well followed — all these things count — but they lead only to a certain point. Ultimately — every man has to be weighed — and if found wanting nothing can procure him the public confidence.

Nor would I desire it under such circumstances.

January 28

Dearest Mamma,

I sympathise with all your extravagances — even more than you do with mine — it seems just as suicidal to me when you spend £200 [£24,700] on a ball dress as it does to you when I purchase a new polo pony for £100 [£12,350].And yet I feel that you ought to have the dress & I the polo pony. The pinch of the whole matter is we are damned poor.

That summer, Winston spent three weeks in England. At his request, his mother had arranged for him to address a political meeting in Bradford.

July 15, Bradford

My dearest Mamma,

The meeting was a complete success.I was listened to with the greatest attention for 55 minutes at the end of which time there were loud & general cries of ‘Go on’. Five or six times they applauded for about two minutes without stopping and at the end of the peroration many mounted their chairs.

Personally — I was intensely pleased with the event.The keenness of the audience stirred my blood — and I certainly succeeded in rousing & in amusing them. They burst out of the hall & pressed all round the carriage to shake hands and cheered till we had driven quite away.

The conclusions I form are these — with practice I shall obtain great power on a public platform.My voice sufficiently powerful — and — this is vital — my ideas & modes of thought are pleasing to men.

May 26, 1900, 35a Great Cumberland Place

My dearest Winston

I am intensely proud of you, & apart from this, I understand you as no other woman ever will.Your political career will lead you to big things.

Aged just 25, Winston became Conservative MP for Oldham on October 1, 1900 

  • Adapted from Darling Winston edited by David Lough, published by Head of Zeus on September 20 at £30.To order a copy for £24 (offer valid until September 15; P&P free), visit or call 0844 571 0640. Copyright in Winston’s letters is © The Estate of Winston S. Churchill; Copyright in Lady Randolph Churchill’s letters is © The Master, Fellows and Scholars of Churchill College, Cambridge.