Army Career

He was appointed Second Lieutenant in the 4th Hussars cavalry. In 1895, he went to Cuba as a military observer with the Spanish army in its fight against the independentists. He also reported for the Saturday Review. In 1898 he rode as a reporter with the 21st Lancers at the Battle of Omdurman. As the son of a prominent politician it was unsurprising that Churchill was soon drawn into politics himself. He started speaking at a number of Conservative meetings in the 1890s. It was noticeable that in the first few years of his political career, and again in the mid-1920s, he frequently used his father's slogan of "Tory Democracy". Many were to regard Churchill in his early years as being obsessed with continuing his father's battles from fifteen years earlier. In 1899 he was considered as a prospective candidate for Oldham. One of the town's two MPs had died, and with the other in ill health he was persuaded to resign so that both seats could be elected together. Churchill found himself thrust into a prominent by-election, alongside James Mawdsley, the Lancashire general secretary of the Amalgamated Society of Cotton Spinners and one of the few prominent Conservative trade unionists. The Liberal candidates were Alfred Emmott and Walter Runciman, who later sat in the Cabinet alongside Churchill. The by-election was dominated by a number of issues, including a Clerical Tithes Bill in Parliament, the brunt of criticism for which fell upon Churchill as a candidate for the governing party and the only Anglican of the four (though he was non-practicising). Facing attacks on the Bill, Churchill repudiated it. He later commented "This was a frightful mistake. It is not the slightest use defending Governments or parties unless you defend the worst thing about which they are attacked." The Conservative leader in the Commons, Arthur Balfour commented "I thought he was a young man of promise, but it appears he is a young man of promises." Despite this, Churchill and Mawdsley narrowly lost the marginal seat, though with no harm to themselves as the Conservative government was facing a period of unpopularity. Runciman is reported to have commented to Churchill: "Don't worry, I don't think this is the last the country has heard of either of us." Churchill then became a war correspondent in the second Anglo-Boer war between Britain and self-proclaimed Afrikaaners in South Africa. He was captured in a Boer ambush of a British Army train convoy, but managed a high profile escape and eventually crossed the South African border to Lourenço Marques (now Maputo in Mozambique).