Book cover provided by Penguin Random House

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One night in the summer of 1929, Winston Churchill, who was staying in a bungalow owned by William Randolph Hearst, was horrified to see a bulky figure clambering through his window. 

The intruder, Winston realized, was his son Randolph, who seemed equally startled. Randolph had expected to find Hearst’s daughter-in-law, who he’d spent the afternoon flirting with beside a sapphire bathing pool. The sight of Winston, angry as a rogue elephant, must have been a disappointment. 

Nevertheless, it was another example of the possibilities and excitements that the Churchills’ trip to the United States had opened up. You didn’t get those sorts of opportunities back in London, with its watchful mothers and tenacious chaperones. 

Winston and Randolph, accompanied by Winston’s brother Jack and Jack’s son Johnny had set sail for North America that August. Officially, he was making the journey to earn money dispensing old world wisdom on the lucrative new world lecture circuit. But in truth, Winston’s career had stalled, perhaps fatally: although he had been returned to his seat in Parliament, the voters had cast out the Conservative Party, and he was trying to imagine the future. Only three months earlier, he had been Chancellor of the Exchequer: when the prime minister Stanley Baldwin resigned, it was rumored, Winston would be called to step into his shoes. Instead the Tories had lost the May election, and Winston was increasingly estranged from his party. Although he did not quite realize it yet, his time in the wilderness had begun.

All of this must have churned through his mind as what Winston called ‘the Churchill Troupe’ zipped through Canada on a luxurious train, complete with three bedrooms, two bathrooms, four toilets, and an observation platform. Wherever they stopped, Winston would address gatherings of eminent citizens. Sometimes Randolph, who slept for up to ten hours at a time, ate ‘enormously’ and seemed to grow, physically and intellectually, a little more each day, was asked to add a few words of his own.

Winston was delighted both by the pace of their tour—‘We have never ceased traveling, starting, stopping, packing, unpacking, scarcely ever two nights in one bed except the train; & eight nights running in that’—and by the enthusiastic reception he received in Canada. ‘Never in my whole life have I been welcomed with so much genuine interest & admiration as throughout this vast country,’ he wrote. 

But what gave him most pleasure was the companionship of the son he adored. His letters home hum with praise and affection. He was enchanted by Randolph’s beauty, his cleverness, his boldness. The energy and potency that spilled out of his son’s body seemed to match the vibrancy of the country they were traveling through.

And this meant that Winston began to entertain an idea that had already swum into his consciousness once or twice before, one that would have altered England’s history. For many years, his sense of having been picked by fate for a hero’s role, his conviction that he would die young, and his desire to escape the feelings of worthlessness that had afflicted him for so long, meant that Winston felt compelled to conduct his life in a blizzard of frenetic activity. 

Now, however, another future became possible, one in which Randolph’s destiny took pride of place. Winston contemplated clearing out of politics altogether and moving to Canada to make a fortune. His own father, Lord Randolph had belittled and ignored him, but had been considerate enough to succumb to a mysterious disease in his forties. When Winston began his own career, therefore, he had a clear run at a seat in Parliament. By removing the white-hot glare of his own charisma from the scene, at a moment when his own career had stalled, he could do the same for the son he so desperately wanted to become prime minister in his stead. 

But in the meantime, a holiday was in order. For the next weeks, the little party swept down into the United States. Despite Prohibition, and dinners with bishops, Randolph topped up Winston’s coffee cup with brandy whenever he saw that nobody else was watching. In California, the pink-skinned Winston bought his first ten-gallon hat to protect himself from the sun. The group stayed at the extraordinary Hearst mansion at San Simeon, with its ridiculous replica of a Moorish church and a park in which exotic animals like llamas, giraffes, and elephants ran ‘quite wild’. 

Even more exciting was Hollywood, where Charlie Chaplin, an old acquaintance, showed them the film industry’s magical studio lots and took them to star-studded parties. At every stop, Winston would visit the stock exchanges housed in all of the big hotels. While the politician revelled in the success of his investments and financial speculations, Randolph would try to smuggle another actress into his room.

After all, America was theirs too—Winston’s own mother Jennie was, after all, a native of New York. Both men were, in their own ways, in love with the continent and everything it promised. In the years that followed, whatever the vicissitudes of their lives in Britain, the Churchills could always rely on a warm welcome on the other side of the Atlantic. 

But almost everything else in their future was far less sure. And while the lecture tour was a happy interlude, when anything seemed possible, reality was different. In the end, Winston did not turn away from politics. Randolph did not get even close to becoming prime minister. Winston, however, did, and in the process became his country’s saviour in a war no one could yet imagine in 1929. Randolph became a chaotic failure who could never quite reconcile his passionate love for his father with the resentment and bitterness he felt towards him. 

And while the trip may have brought two people who were already intimate even closer, it also sowed the seeds of their differences—and the tensions that in a decade’s time would drive them irrevocably apart.

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Josh Ireland has written for the Daily Telegraph, Prospect, Spectator, and the Times Literary Supplement. He is the author of Churchill & Son (Penguin Random House, 2020.)

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