The young Winston Churchill overcomes a bad family life and early military mistakes to launch his political career.

In 1897, newly commissioned Second Lt. Winston Churchill, the twenty-three-year-old son of Lord Randolph Churchill, former Chancellor of the Exchequer and notable Conservative member of Parliament, is in India to fight rebel forces as well as report the action as a correspondent for the London newspaper The Daily Telegraph . Despite the disdain of his superior officers, particularly commanding general Lord Kitchener, for what they perceive as Winston's naiveté and fool-hearted bravery, Winston is determined to act both honorably and heroically: As a boy of seven, Winston is taken to boarding school by his American-born mother, Jennie Jerome Churchill, a fashionable, socially prominent woman, whom young Winston adores as a "fairy princess." Despite his frequent letters imploring them to visit, Jennie and Randolph rarely see the lonely boy, whose most beloved companion is his nurse, Mrs. Everest, whom he calls "Womany." When Winston is cruelly beaten for a minor infraction by his sadistic headmaster, Womany firmly tells Jennie that he will not return to that school. Throughout his adolescence, Winston works hard, first at the prestigious public school Harrow, then at Sandhurst, the British military academy, but he is a poor student, much to the consternation of his stern father. Some time after Randolph resigns his position as Chancellor of the Exchequer following a political disagreement with his party over support for the military, he begins to exhibit periodic and increasingly erratic behavior. Although only the shattered Jennie knows that doctors have diagnosed Randolph with syphilis, the amiable Winston maintains his respect and love for his father, despite Randolph's almost constant rebukes and frequent fits of anger. After Randolph dies at the age of forty-six, the much younger and still beautiful Jennie is left nearly destitute after the family's money is lost in the American stock market, forcing Winston, who is barely in his twenties, to try to support her in the manner in which she has always lived. Through Jennie's social connections, Winston accepts a commission in the British Army that will enable him to report on battlefield activities in India for The Daily Mail . Despite his bravery and growing fame as a writer, Winston continues to be frustrated in his attempts to advance in the Army and writes to Jennie asking her to seek a commission for him in the Sudan. She then writes a pleading note to Lord Kitchener, who rebuffs her in a scathing note to her, the Prince of Wales and others stating that he has no intention of acquiescing to her demands. A short time later, without Kitchener's knowledge, Winston is sent to the Sudan, where he warns the surprised and irritated Kitchener of the imminent advance of the warring Dervishes. After the British are victorious, the now twenty-four-year-old Winston returns home to England, and is coerced by Jennie to stand as a Tory in his father's old Parliamentary district of Oldham. Winston works very hard to win the election, but his lack of experience and a youthful speech impediment, which he has yet to overcome, lead to his defeat. In 1899, at the start of the Boer War, Winston again gains a commission through his mother's intercession and travels to South Africa, where his seemingly fool-hearted bravery again provokes both amusement and irritation among his superior officers. A short time after his arrival, Winston and fellow officer Aylmer Haldane are captured by the Boers as they valiantly defend a British troop train. Imprisoned with Winston near Pretoria, South Africa, Haldane and another officer plan an escape but scorn Winston's enthusiastic assumption that he will go with them. Reminding Haldane that he could have gotten away had he not gone back to the train to help Haldane, Winston shames him into relenting, and they escape one night through the prison latrine. Winston makes his way through South Africa by hiding in a coal car, then jumps off the train before it reaches the border inspection point. Winston eventually makes his way to the home of a farmer named Howard, who, unknown to Winston is English and has secretly been helping British soldiers to escape. For three days Winston is hidden with several other men in a coal mine, where he meets Dewsnap, an Englishman who says that his wife is from Oldham and is an admirer of Winston. While the world's press recounts sensationalized stories of Winston's escape and supposed recapture, with Howard's help, Winston flees on a train to British territory. Jumping to the roof of the train as it passes the frontier to safety, Winston shoots his pistol in air, yelling "I'm free, I'm Winston Bloody Churchill and I'm free." After rejoining the army and helping to free the remaining British prisoners in Pretoria, Winston returns to England, where he is hailed as a hero and wins the Oldham seat in the next Parliamentary election. Although Jennie is proud of him, she fears that his lack of oratory prowess and frequent agreements with Liberals such as David Lloyd George over leaders of his own party will lead to the same downfall as Randolph. However, one evening, when Winston delivers a moving speech in the House of Commons referencing the "tattered flag" of his father's position on military funding, Jennie beams at him from the gallery. Later, after Winston has received resounding cheers and congratulations for his speech, he listens to Jennie discussing his future and casually asks to be introduced to a young woman he saw in a pale yellow dress. Jennie smiles as she tells him that the young woman's name is Miss Clementine Hozier.