Like Trevelyan, Winston Churchill (1874–1965) was born into a highly privileged family, indeed one at the pinnacle of the aristocracy. But unlike Trevelyan, who was financially secure throughout his life from family money, Churchill had to make his own way. Imitating his parents, the flamboyant and impecunious Lord Randolph Churchill and the free-spending American heiress Jenny Jerome, he was beset throughout his life by one financial crisis after another. Temperamentally, the two men were poles apart, with the cautious, introverted Trevelyan embracing the quiet and seclusion of a well-ordered life, while Churchill loved society and lively company. The former's pastoralism and longing for simpler, less hectic times made him uncomfortable in the frenetic twentieth century, while Churchill relished the challenges of modern times. Both men held conservative views about government and society, but Trevelyan's were more rooted in an imagined, benign early Georgian social order, while Churchill celebrated the ability of the aristocracy and the upper classes to maintain a measure of authority into his own day.

Trevelyan's immersion in the quiet rigour of a scholarly existence was natural to him, while Churchill was clearly marked out for a vivid public life, one that was both contentious and (to use a term that frequently occurs in his written works), thrusting.