In 1890, fifty long years before he confidently led the United Kingdom to victory against Nazi Germany in World War II, future prime minister Winston Churchill was an easily distracted, underachieving fifteen-year-old coasting through life at London’s Harrow School, where he boarded full-time during term. In June of that year, his notoriously strict mother, Lady Randolph Churchill—whom he claimed to have loved ‘dearly, but at a distance’—came face to face with a school report that left her feeling less than enthused. Never one to couch her words, she reacted by way of this letter to her son, one of many she wrote to him over the years. Winston’s reply came a week later.

June 12, 1890

2 Connaught Place

Dearest Winston,

I am sending this by Everest [Winston’s nanny], who is going to see how you are getting on. I would go down to you — but I have so many things to arrange about the Ascot party next week that I can’t manage it.

I have much to say to you, I’m afraid not of a pleasant nature. You know darling how I hate to find fault with you, but I can’t help myself this time. In the first place your father is very angry with you for not acknowledging the gift of the £5 for a whole week, and then writing an offhand careless letter.

Your report which I enclose is as you will see a very bad one. You work in such a fitful inharmonious way, that you are bound to come out last — look at your place in the form! Your father & I are both more disappointed than we can say. If only you had a better place in your form & were a little more methodical I would try to & find an excuse for you.

Dearest Winston you make me very unhappy — I had built up such hopes about you & felt so proud of you — & now all is gone. My only consolation is that your conduct is good and you are an affectionate son — but your work is an insult to your intelligence. If you would only trace out a plan of action for yourself & carry it out & be determined to do so — I am sure you could accomplish anything you wished. It is that thoughtlessness of yours which is your greatest enemy.

I will say no more now, but Winston you are old enough to see how serious this is to you — & how the next year or two & the use you make of them, will affect your whole life. Stop & think it out for yourself & take a good pull before it is too late. You know dearest boy that I will always help you all I can.

Your loving but distressed
Mother

[19 June 1890]

Harrow

My darling Mummy

I have not written till now because I can write a much longer letter. I will not try to excuse myself for not working hard, because I know that what with one thing and another I have been rather lazy. Consequently when the month ended the crash came I got a bad report & got put on reports etc. etc. That is more than 3 weeks ago, and in the coming months I am bound to get a good report as I have had to take daily reports to Mr Davidson twice a week and they have been very good on the whole.

And then about not answering Papa’s letter — I did that very evening & I gave it to the Page to put in the Pillar box & a 1ᵈ for him at the same time.

I could not put it there myself because it was after Lock-up. He I suppose forgot and did not post it until several days had elapsed. My own Mummy I can tell you your letter cut me up very much. Still there is plenty of time to the end of term and I will do my very best in what remains. [...]

Good Bye, my own,
With love I remain, Your own
Winston S. Churchill

Excerpted from the book, Letters of Note: Mothers. Reproduced with permission of Curtis Brown, London, on behalf of The Master, Fellows and Scholars of Churchill College, Cambridge © The Master, Fellows and Scholars of Churchill College, Cambridge / Reproduced with permission of Curtis Brown, London, on behalf of The Estate of Winston S. Churchill. Copyright © The Estate of Winston S. Churchill.