Sandhurst Victories: Winston entered the Royal Military College at Sandhurst as a cavalry cadet because he had not qualified for the infantry, a circumstance of great disappointment to his father. He would soon be granted an opening in the infantry, but shortly after he entered school he was invited to attend a mess of the Fourth Queen’s Own Hussars, a light cavalry regiment. That experience and his love of horses convinced him that a successful military career would most likely be with a cavalry regiment. Eventually he would serve in nine British regiments – the Fourth Hussars, Thirty- first Punjab Infantry, Twenty-first Lancers, South African Light Horse, Oxfordshire Hussars, Oxfordshire Yeomanry, Grenadier Guards, Royal Scots Fusiliers, and Oxfordshire Artillery,
The Churchill family financial fortunes were depressed, as were their political experiences. This resulted in the dismissal of Mrs Everest, Winston’s beloved ‘Woom.’ In October he wrote Lady Randolph, “… if I allowed Everest to be cut adrift without protest in the manner which is proposed I should be extremely ungrateful—besides I should be very sorry not to have her at Grosvenor Square, because she is in my mind associated more than anything else with home. She is an old woman – who has been your devoted servant for nearly 20 years – she is more fond of Jack and I than of any other people in the world and to be packed off in the way the Duchess [of Marlborough] suggests would possibly, if not probably, break her down altogether.” Although Lord Randolph gave Mrs. Everest periodic “presents,” she had to depend on her sisters for support. Nevertheless, she never forgot Jack and Winston on their birthdays and at Christmas.
Winston’s first set of examinations at Sandhurst showed his inclination for military studies (maximum score 300): Military Administration 230, Military Law 276, Tactics 278, Fortification 215, Military Topography 199. Of a possible 1500 marks he received 1198. His conduct was rated ‘good but unpunctual.”