Winston's father, determined that his son should pursue a military career, had him enrolled in the army form in Harrow, and for the next three years he trained as a soldier, finally managing to gain admission to the prestigious military academy at Sandhurst as a cavalry officer. It should be noted though that this was no natural conclusion either; in order to make it, Winston had to secure the services of what was known as a “cram master”, someone who would tutor him and advise him on his subject, and this was on his second attempt, therefore it was on his third that he finally made it into Sandhurst.

Once in, though, he finally started to show the promise and aptitude that some of his teachers had seen dormant in him, and by the time he left in 1894 he was already on his way to a commission as a second lieutenant in the Hussars. Unfortunately, a month after leaving Sandhurst his father died, an early age even for that time, passing away in January of 1895 at the age of forty-six. What should have been a traumatic and painful time for the young Winston (now 20) was probably lessened by the lack of contact he had had with Lord Randolph, his father almost a stranger to him. A few months later he took up his commission in the 4th Hussars.
While I don't wish to draw too close a comparison between him and his contemporaries on the other side, a military man is a military man, and like Hitler and Goring (more Goring really, as Hitler never went to any military academy but simply signed up for the army), Winston Churchill only really began to shine once he entered the army. Here, he could forget the hated Latin and Greek: a soldier had no need for such classical knowledge, and the only use he had for mathematics would be to establish whether the opposing force was bigger than his, or whether he had enough ammunition. However, no man ever entered Sandhurst or any other military college without at least a grounding in maths, and indeed Churchill had been forced to cram figures and equations into his mind in order to pass the entrance examination, though he later shrugged that the knowledge, once it had served its purpose (i.e., got him into the academy)
“passed away like the phantasmagoria of a fevered dream”. Maybe it was as well he forgot it, considering the kind of almost insurmountable odds Britain, under his leadership, would face in the summer and autumn of 1940 as it strove to survive the Nazi onslaught. A man with a better grasp of figures (and thus, reality) might have been more amenable to a compromise than he.
A year after his promotion to second lieutenant, he and his regiment were shipped almost five thousand miles southeast, to begin a whole new chapter in the life of the man who would one day be voted as the greatest of Britons.
II: Churchill in India – Empire and Empowerment
It used to be said that the sun never set on the British Empire, and this had two meanings: one, a sort of metaphor for the supposed immortality of the empire, that it would never fall, but also a literal one. As Britain had colonies all over the globe, when it was night in England you could be assured that in some other corner of her far-flung empire it was day, so that at its height, Britain could indeed boast that the sun, in a very real way, never set on her dominions. And it was here, in the country deemed the jewel in Queen Victoria's crown, where she was known (to British if not Indian subjects) as the Empress of India, that life finally began to open up for Winston Churchill.
He arrived in Bombay (now known as Mumbai) in October 1896, four weeks before his twenty-second birthday, and at the height of British power in the colony. The Queen was about to celebrate her Diamond Jubilee, having reigned for sixty-five years, making her by far the longest reigning monarch England had ever had (and only beaten today by the current Queen), and while there had been the “unfortunate unpleasantness” of the Indian Revolt of 1857, all of that had been sorted out now and the Indians were once again good and obedient subjects of the Crown. A posting to India was generally seen as a cushy job – the working day lasted three whole hours, and the rest of the day, from 10:30 onwards, was the soldiers' own to do as they pleased, to say nothing of having their every need pandered to by a flotilla of Indian servants – but Churchill didn't do cushy, and he wasn't about to relax here for the next few years.
In fact, he spent only nineteen months in India, while his regiment remained there for eight and a half years. In that time, he visited England twice, for three months at a time, Calcutta three times and even went as far as Hyderabad, over three hundred and fifty miles north, to take part in a polo contest, polo being the one sport he was ever interested in. Added to this, he undertook his own expedition to the northwest frontier, where he catalogued his travels. It was in Bangalore, where his regiment had moved three days after arriving in Bombay, and where they were to be stationed for the duration, that Churchill began to feel (again, and with apologies to any English readers, like Hitler) that he had a destiny to fulfill. He knew serving in India for eight years was not part of that, and he began to rue his failure to learn Latin and Greek, wishing to read more of the classics and improve his, up to then, quite basic education. He still couldn't face learning these dead languages, he just wished he already understood and could read them. He considered leaving the army and going to Oxford, but it was a little late in his life for that. He would have had an awful lot of catching up to do, and as we have already seen, he wasn't the kind of student who could expect to manage that.
A letter to his mother offered him no encouragement in return – again, Winston's love and regard for Jennie didn't quite, but almost did, vary inversely with that of his mother for him. She just was not interested, and left her son to sort out his own problems. With her husband dead, she was happy to take a string of lovers, and he was possibly an unwelcome reminder that she had once settled for a stuffy old English aristocrat who was not worthy of her. She was having fun, still young, still beautiful, and she didn't need her son from another marriage spoiling it for her. She would marry twice more before her death, the first to take place at the very turn of the century, only a few years away. But meanwhile she was becoming the darling of society, and in particular the Prince of Wales (who, you might recall, had originally introduced her to her late husband), freed from the bonds of matrimonial responsibility.
We could, I suppose, castigate Jennie for this seemingly unbecoming behaviour, with her husband only a year dead, but then we should remember two, or perhaps even three things: one, she was young and beautiful, two she was American, and three, her marriage to Lord Randolph had quickly soured, and she was said to have had lovers even during the time they were together, so perhaps it's not such a surprise to read that she took to her freedom like an imprisoned butterfly suddenly loosed from a jar, and spread her wings, courting all comers. None of this helped her son, of course, who decided his best course was to self-educate, and asked her to send him various books, which, to her credit at least she did. He then made himself familiar with the classics, history and most especially politics, which he had started to take a keen interest in. Perhaps this had to do with his father having been an MP (if not a very successful one) or perhaps it had no bearing on his interest at all. What it would do was prepare him for the life he was to lead, the position he was to occupy, and secure forever for him one of the highest and most exalted places in history.

One point on which his mother did correspond with her son, and very angrily too, was the subject of his spending. She wrote in one letter that if he could not live within his means he would have to resign his commission and come home. She made it clear she was not going to continue to support him on her own if he would not rein in his reckless spending. Nevertheless, he used his mother's considerable political connections, not to avoid postings to the front, but to obtain them. A young man lounging in the heat of India looking for a fight, he sought conflict everywhere and wherever there was a battle, an engagement, a civil war or some sort of action, he wanted to be there. The spirit of adventure was hot in his blood, and he wanted to make a name for himself. He was also eager to do this through the means of politics, and to that end was aided by an American Representative and failed candidate for president, Bourke Cockran, who took him under his wing when he visited New York on his way to fight rebels in Cuba, and taught him much about politics.

Time spent with Cockran imbued in the young Winston an abiding fascination with and love for America, which would carry over of course into his relationship with President Roosevelt, and perhaps lay the foundation for the close ties between both countries over the following centuries. He was thrilled with New York, where he stayed and was entertained at Cockran's Fifth Avenue apartment, and at how eager everyone was to make his stay as comfortable as possible. But comfort was never Churchill's game, and when, on leave home in England, word came to him of an uprising on the border between India and Afghanistan, he cut short his holiday to rush to be there, pressing his friend, Major-General Bindon Blood, to approve his Hussars being posted there. It took him over a month of travel, and even then Blood's reply to his request was non-committal at best:
'Very difficult; no vacancies; come up as a correspondent; will try to fit you in. B.B”. But he continued on in high spirits, sure he would see action and champing at the bit to be there, no doubt worried it would all be over by the time he arrived.
It was not an easy, not a short journey from Bangalore (he had to return to his headquarters first to ask permission of his commanding officer to go on the expedition) and most men would have written their account of it as a complaint, or a testament to their misery, but for Winston there was a sense of adventure and even joy when he wrote
“I had the curiosity to ask how far it was. The polite Indian [booking clerk] consulted a railway time table and impassively answered, 2,028 miles. . . . This meant a five days' journey in the worst of the heat. I was alone; but with plenty of books, the time passed not unpleasantly. Those large leather-lined Indian railway carriages, deeply shuttered and blinded from the blistering sun and kept fairly cool by a circular wheel of wet straw which one turned from time to time, were well adapted to the local conditions. I spent five days in a dark padded moving cell, reading mostly by lamplight or by some jealously admitted ray of glare.”
Of course, with this being, as mentioned, the Queen's Diamond Jubilee, he was probably more anxious than ever to make a good impression and have something to boast of, and accounts of his valour to be read in the newspapers. One thing which would become very clear about Winston Churchill from the beginning of his career (and again, we have to acknowledge that this was the case with his two main Nazi counterparts, and is, in fairness, most likely true about most famous men) was that he was one of his own best promoters, never missing a chance to be in an action and then ensure it was written about, using his wit and his (later) reading to make comments, quips and indeed speeches that have lasted the test of time and are used to point to the man's incredible grasp of and manipulation of the English language, and to build up his own legend. This legend was reinforced – or, if you prefer, first began to show itself – in his amazing work ethic and endurance. Having spent six weeks at the front with Blood, he then returned to Bangalore to work on an account of the battle which ended up running for 85,000 words, while also writing his first and only novel. Although Lady Randolph had his account,
The Story of the Malakand Field Force, published without delay, it was riddled with punctuation errors and other things which should have been caught by any competent proof-reader, and Churchill was disappointed with the many mistakes which had been left in it.
Nevertheless his writing became widely admired, mostly due to the patronage of the Prince of Wales: when His Highness remarks on how splendid a book is, it's almost incumbent on anyone and everyone who wishes to get on to make sure they read it too, and have an opinion about it that supports the future king of England. Interestingly, a few months later the roles were reversed between Churchill and his mother, with she requesting (a cross, in her case, between a demand and an entreaty which surely stuck in her throat after having taken him to task about money) a loan, to be secured against his trust fund, which he grudgingly, but it has to be supposed with a certain sense of satisfaction and triumph, agreed to. Although they had never been as close as Winston would have wished – not close at all, in fact – the issue of money, and in particular the swift and somewhat brutal removal of the moral high ground from beneath her very feet, as she had to go, proudly and arrogantly but still symbolically cap in hand to her son for money, soured their relationship, on both sides.
Winston, though he had more or less precipitated the rift, was the first and the most eager to close it, asking her to resume the correspondence she had cut him off from, but she remained obdurate, most likely smarting from his rebuke in the way no parent can take a dressing-down from their own child. Despite this, she was still ready to do what she could to advance his political ambitions, and arranged many meetings, luncheons and teas with powerful and influential figures of her acquaintance, out of which came precisely nothing. Nevertheless, due to what to him were fortuitous circumstances, he was in Cairo by early August 1898 and almost immediately joining his regiment on a 1,400-mile trek north to Luxor, in order to take part in the engagement at Atbara. After the successful campaign, in which it is said he both distinguished himself and was miraculously untouched, he decided his future did not after all lie in the army, and resigned his commission, to go instead into politics.