Father and Son Randolph and his father had a loving but often contentious relationship

Randolph perhaps epitomises the difficulty of being the son of a famous father. In his twenties, he veered between adoration of his father and bitter accusations of being treated as a ‘wayward and untrustworthy child’, interspersed with periods of excess drinking and ill-considered political initiatives.

Randolph duly stood for parliament in the 1930s but despite the obvious advantage of his father’s support, he was defeated each time, being seen – in true Churchill style – as a political maverick. He was elected as MP for Preston in 1940 but lost his seat at the 1945 General Election. While he had his father’s weaknesses (notably, obstinacy, arrogance and bad temper), he did also inherit some of his strengths, including a gift for writing and considerable personal bravery, serving with the newly formed Special Air Service (SAS) and conducting dangerous missions in the Libyan Desert and Yugoslavia. Yet, ultimately, he lacked his father’s political skills, charm and charisma.

Churchill no doubt loved his son, but sometimes despaired of him. Their strong personalities would often clash.

Their father–son love–hate relationship was never entirely resolved, although there was seemingly a reconciliation in later life when Churchill approved Randolph’s appointment as his official biographer in the early 1960s.

And it’s clear that, despite their lifelong differences, Randolph never stopped worshipping his father, just as Churchill had worshipped his father a generation earlier.

Randolph married twice, first to Pamela Digby (later Harriman) in 1939, with whom he had a son, Winston, and then to June Osborne in the late 1940s, with whom he had a daughter, Arabella. Neither marriage was a success. He went on to carve out a name for himself as a gossip columnist and writer, but died in 1968 without having fulfilled his father’s expectations – and before he could complete his father’s biography (though he did see the first two volumes published).

To learn more about Churchill’s son, Randolph, read the ODNB entry for him here.

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