Winston Churchill first set foot on American soil on November 9, 1895. The twenty-year-old junior army officer’s regiment, the socially elite1 4th Hussars, had been granted ten weeks’ leave, time off to prepare for his regiment’s departure to India. Churchill “…began to look around for… some more exciting adventure”2 than the socially approved fox hunting that recommended itself to his colleagues. “Even the smallest kind of war,” he later wrote, “was the swift road to promotion and advancement… It was the glittering gateway to distinction. It cast a glamour upon the fortunate possessor alike in the eyes of elderly gentlemen and young ladies.”3
The young subaltern4 decided on Cuba, where the Spanish army was battling to put down insurgents fighting for independence from Spain. Involvement in Cuba would necessarily involve passing through New York City, an added advantage.
The stay in New York proved to be more than a way station en route to Cuba and adventure, fame, and literary fees. It was the beginning of a love affair with America and an enduring intellectual partnership with Bourke Cockran, a New York Democratic congressman whom Churchill would later describe as “the biggest and most original mind I had ever met…. I feel I owe the best things in my career to him.”5
The receptions Churchill received, both in New York and in Cuba as the nineteenth century was coming to its close, were not available to almost anyone whose mother was not Lady Randolph Churchill, née Jennie Jerome, a stunning and vibrant international socialite and hostess to the rich and famous on two continents. Jennie used her extensive network to advance her son’s interests at every opportunity, at least once he had graduated from schoolboy into an interesting adult. Churchill would later write of his mother, “In my interest she left no wire unpulled, no stone unturned, no cutlet uncooked.”6
By the time Churchill arrived in New York, Jennie had forged a close friendship with the extraordinary American congressman Cockran. Cockran ranked among the great orators and conversationalists of his time, famed for his “sparkling wit”7 and whose “wit, wisdom, and elegance exceeded those of Carlyle and Gladstone” according to Lord Ripon,8 who professed to having heard both speak, a view supported by Churchill, who declared Cockran’s “conversation, in point, in pith, in rotundity, in antithesis and in comprehension, exceeded everything I have ever heard.”9
In March 1895, Cockran met Lady Randolph Churchill, who had repaired to Paris to be with her family shortly after her husband’s death. Jennie’s loneliness and sense of loss dissipated in early spring when she met Cockran, whose wife had recently died in childbirth one year after their marriage. A beautiful, intelligent widow and a brilliant, still-young widower, in Paris in the spring, the result inevitable. Or not. Churchill’s most recent biographer describes Cockran as “an admirer of Jennie’s”10 and Churchill wrote he was “a great friend of my American relations.”11 Intimates of the pair expressed varying views about the nature of their relationship. Whatever the truth, there is no doubt that Cockran “had done wonders to revive Jennie’s spirits…. She was once again in touch with life,”12 writes one of her biographers. When Cockran left Paris to return to America, he suggested to Jennie that if young Winston happened to be passing through New York, “he would be happy to meet him, and talk politics, and perhaps pass on a few tips.”13
True to his word, Cockran met Churchill as his ship docked. The press took some notice, largely because of the arrival’s famous name. The New York Times on November 20, 1895, ran a seven-line item headlined RANDOLPH CHURCHILL’S SON IN CUBA, prompting Winston’s eventual official biographer, Sir Martin Gilbert, when reporting the article, to comment, “Churchill was still best known as his late father’s son.”17
Reporting was not always completely accurate. The American press variously described the young army officer as Lieutenant General Winston Churchill, Lord Churchill and “Lieutenant of huzzards in the Spanish army in Cuba.”18
Cockran immediately whisked Churchill and his traveling companion and friend, fellow subaltern Reginald Barnes to his elegant 763 Fifth Avenue flat. Churchill’s first experience with American hospitality proved a pleasurable one. The flat was, he wrote to his mother, “charming and comfortable… It is very pleasant staying here as the rooms are beautifully furnished and fitted with every convenience & also as Mr. Cockran is one of the most charming hosts and interesting men I have met.”19
To his aunt Leonie (Lady Leslie), a friend of the congressman, he wrote that Cockran “is such a nice man and we have made great friends.”20 Cockran arranged a dinner at his flat on Churchill’s first night in New York to introduce him to about a dozen important members of the bar, including a Supreme Court justice. Other luncheons and dinners were scheduled at which Churchill was introduced to a good portion of the city’s elite. As Churchill described to his mother, “…we have engagements for every meal for the next few days about three deep.”21
Cockran also organized a tour of fire stations, West Point and other military installations, and of the new ironclad cruiser, New York. “…we have been shewn [sic] everything,”22 Churchill reported to his aunt. Perhaps fearful that his host might overlook something, Jennie’s New York cousins “had engaged an excellent valet” to care for the two young lieutenants when they were in New York.23
Churchill’s first impressions of America proved to be enduring. Yes, there was the matter of a certain lack of what older nations would consider “refinement”: the press was vulgar, and the use of paper rather than a coin for the one-dollar currency struck the future chancellor of the exchequer as “disreputable… abominable.”24 But in a single week he sensed the vitality and the virtues of the American people.
He wrote to his brother, Jack, “There was lots to see and do…. This is a very great country, my dear Jack. Not pretty and romantic but great and utilitarian…. A great, crude, strong, young people are the Americans…. A great lusty youth… who moves about his affairs with a good hearted freshness which may well be the envy of older nations of the earth…”25
Thanks to Cockran, Churchill was to meet not only New York’s elite, but people in a variety of walks of life during his stay, which lasted three days longer than originally intended. The sailors he met while touring the ironclad cruiser with Cockran impressed him with “their intelligence, their good looks and civility and their generally businesslike appearance…. it is the monopoly of the Anglo-Saxon race to breed good seamen.”26 This is an observation he might have recalled when appointed first lord of the Admiralty in 1911, and began to sense that a war with Germany might be won or lost at sea.
The businessmen he met, the sort who would be such important contacts in America during his long life, he deemed excellent. “The magnificent communication system [of New York] is due to private enterprise, while the state is responsible for the [abominable] currency; and hence I come to the conclusion that the first class of men of America are in the counting houses and the less brilliant ones in the government.”27 He would later embroider that theory when on speaking tours of America with the thought that in Britain the reverse was true.
He looked forward to the day when he could introduce Jack to America, certain that his brother would “feel as I feel—and think as I think today.”28 More than three decades elapsed before the day arrived, when Churchill brought Jack along on his cross-country tour.
The day for departure to Cuba arrived, and Cockran gallantly took on the burden of seeing to it that Churchill’s round trip between New York and Cuba would be as comfortable as possible, perhaps unintentionally setting a standard that Churchill would thereafter find agreeable. That standard would include accommodations that not only provided for Churchill’s personal comfort, but also included facilities that would enable him to continue working at the relentless pace he maintained in his offices and homes. If cruder facilities were all that was available to get to a war or adventure, they would suffice. Later in life, when tours of America were on his schedule, travel would include a mix of private railcars provided by wealthy American admirers, and mad dashes to catch trains with only his protective detective to help with luggage and arrangements. For now, staterooms would do. Cockran had arranged “nothing less than a stateroom on the train” to Tampa, arriving November 18, from whence Churchill and Barnes sailed to Havana aboard “a perfectly acceptable smaller steamship,”29 the “very clean” SS Olivette,30 which stopped in Key West to pick up mail and additional passengers bound for Havana. The subalterns arrived in Havana November 20 after what the young Churchill described as “a comfortable journey from New York”31 in his own stateroom on the Olivette. For the return trip to New York, Churchill asked Cockran to arrange a stateroom on a ship sailing directly from Havana to New York, but without intermediate stops as experienced en route to Cuba.32 Apparently, that proved impossible, so it was back to Tampa on December 9, where one press report tells us that “Mr. Churchill is accompanied by… his chum… [and both] enjoyed a day shooting quail.”33 And then it was on to New York by train, arriving December 10.34
But only after a Cuban adventure that would accomplish what he sought to accomplish: “advancement,” “distinction,” and “glamour,” as well as a medal and experience as a war correspondent. His mother, who had arranged the access to Cockran that elevated Churchill above the status of ordinary tourist, performed a similar feat to assure that her son would arrive in Cuba elevated past an ordinary tourist to that island, courtesy of her social and political network in Britain and beyond.
Jennie spoke to the British minister for foreign affairs, who in turn spoke to the minister of war, who provided a letter of introduction through the British consul-general in Havana35 to Captain-General (sometimes known as Marshal) Martinez de Campos of the Spanish forces in Cuba.36 Even the British ambassador to Spain was eager to help, as he had been an old colleague of Lord Randolph. Lord Randolph’s old friends would be useful to his son.37
Thanks to Jennie, the commander in chief of the British Army, Viscount Wolseley, had recently introduced Churchill to a British audience as Churchill had lectured in several cities across Britain. This permitted Churchill, a young, lower-level army officer, to gain access to Wolseley to discuss his plans for Cuba. He reported to his mother that “Lord Wolseley… was most amiable. He said he quite approved [of my adventure] but rather hinted that it would have been better to go without asking leave at all. However, he said he would arrange things for me… appointing a day on which I shall go and see the head of the Intelligence Department.”38
That same day an official in the Horse Guards War Office advised Churchill, “I am directed by the Commander-in-Chief to inform you… that an application received in this Department through the usual channel will be considered.”39
The director of military intelligence provided maps and asked Churchill to send news about the effectiveness of a new bullet,43 probably stimulating what would become Churchill’s lifelong fascination with military intelligence and armaments. This “invests our mission with almost an official character and cannot fail to help one in the future,”44 enthused Churchill in a letter to his mother. The chain of connections that Jennie had created led to the very top of the military establishment, and her willingness to call on that network made it possible for Churchill to achieve a great deal more by age twenty than most other young men. Of course, the network had to be deployed on behalf of a man willing to give up weeks of sport before going off to India, a man with a taste for adventure and a willingness to take risks. A man with a lively curiosity and a predisposition to know about America, his mother’s homeland. His mother’s willingness to deploy that network on his behalf is a prime example of how Jennie put her network to use in his interests, and how her son extended it as he began learning its value and constructing his own.
As he was to do so often in the future, Churchill combined adventure, journalism, and hoped-for profit. Jennie arranged for him to provide dispatches to Britain’s weekly illustrated newspaper, Daily Graphic, owned by one of her friends.45 Lord Randolph had written for the Daily Graphic on his 1891 tour of South Africa, and those articles were eventually combined in his own book, Men, Mines and Animals in South Africa, with illustrations. His son would write his own books on South Africa.
The five articles, “Letters From the Front,”46 for each of which young Churchill was paid five guineas, ended simply with the initials W.S.C. at the bottom right.47 Later, he became more aware of his need for public credit for his literary outpourings and their importance for his reputation. He would begin to sign his dispatches from India and other places with his full name, and insist that his byline be published alongside his reports and articles. After all, his goal was not only the writer’s fees, but wider recognition of his derring-do and achievements, necessary not only to future reporting assignments but to the launch of a political career with all its attendant expenses. He had determined on a future in politics, and knew he would have to fund his campaigns for a seat in the House of Commons. His mother, whose personal extravagance often took her spending well beyond her resources, and portions of his own, could not afford to provide assistance other than her network.
Churchill accompanied his five dispatches to the Daily Graphic with six ink drawings and sketches.48 Because field photography was in its infancy when Churchill had been at Sandhurst, he was taught to sketch and map territory and fortifications as part of his military training, to which he added sketches of people he came across.49
This skill had been honed at an early age. When fifteen, writing from Harrow, he told his mother he is “getting on in drawing and I like it very much. I am going to begin shading in Sepia tomorrow. I have been drawing little Landscapes and Bridges and those sort of things….”50
In another, later letter from Bangalore in 1898, at age twenty-three, he wrote to his mother: “There is a great deal of work to do here—and as I am a better sketcher than most of the subalterns all the reconnaissance sketching falls to me. I have ridden nearly forty miles this day map making.”51
The aptitude Churchill honed in Cuba would later contribute to his development as a painter, a pastime that helped him to relax when that was key to his functioning, and in his later years to pass time with considerable pleasure wherever he happened to be.
W. L. Thomas, founder and manager of the Daily Graphic, and an engraver, praised Churchill’s letters and sketches: “Allow me to compliment you on the result (as I imagine of your first experiences) as a Special Correspondent and artist combined…. your letters were widely read & appreciated.”52
Good news for a young man hoping to combine reporting with opinion pieces in the part of his career that would be devoted to journalism.
However, Churchill’s experience in Cuba revealed much more than his skill as a journalist and graphic artist. He had come under fire for the first time, seen war up close, and learned how to report on it—lessons he would find useful. It told a great deal about the man, his world view as an imperialist, and his capacity for magnanimity toward a foe. He had decided to fight with an imperialist power to subdue a rebellion. He was the son of a mother from a country that was proud of the success of its battle for independence from Britain. He was heavily influenced by an anti-imperialist American politician with roots in Ireland, urging the president of the United States to intervene in Cuba on the side of the rebels. Churchill nevertheless chose to support Spain, an imperialist power.
Instinct and the nature of his connections in Britain led him to accompany the Spanish forces. He was to defend that move as one based on the opinion of others that the rebels would be incapable of governing Cuba if they came to power. But his magnanimity always shown through: he also expressed admiration of Cuba’s rebel fighters, “their ability to harass the enemy and carry on a guerilla warfare,”53 as he would praise the Boers when touring America to lecture on his capture, escape, and other adventures in Britain’s Boer War in South Africa.
All in all, Churchill’s Cuban adventure was a success, and one that received much-appreciated attention on both sides of the Atlantic. Perhaps best of all, he received a medal, the Cross of the Order of Military Merit, Red Ribbon, First Class, Spain, granted December 6, 1895, ratified January 25, 1896. The citation from the queen regent of Spain read:
I have been notified by His Excellency the Commanding General of the 5th Military District [Suárez Valdés] of the distinguished comportment observed by you in the military action held on the 2nd of this month in Guayos against the joint forces of Máximo Gómez and Maceo… [grant] Red Cross of the Order of Military Merit, First Class, of which I notify you…54
It was handsome, it was of red enamel, and it was one of the rewards for which Churchill had hoped. It could not be worn on a military uniform, a ban he ignored as his career progressed to a point where such rules were not applied to him. As a result of his Cuban experience he was “widely sought after” by Queen Victoria’s son, the Prince of Wales (subsequently King Edward VII), and several of the leading Liberal and Conservative politicians of the age, including Joseph Chamberlain, then colonial secretary; Arthur Balfour, then first lord of the treasury; Herbert Asquith, Liberal member of Parliament; and others of his father’s circle,55 adding satisfaction to his first honor.
Churchill’s approach to his participation in the Cuban uprising proved to be one he would adopt in future such adventures. A bit of pleasure at the start: rum cocktails and a siesta on his first day after meeting up with the Spanish Army.56 As he later described it, “I was handsomely entertained at military headquarters.”57 He found a river in which to bathe, reporting in a dispatch for the Daily Graphic, “The water was delightful, being warm and clear…,”58 a pleasure he would repeat in waters from the Mediterranean, when in the south of France, to the Atlantic, when vacationing in Florida (1946) or meeting with President Eisenhower in Bermuda (1953), although in those instances his swim would not be interrupted by a rebel attack, as was the case in Cuba.
He learned from Spanish soldiers that a short midday nap made one more productive in the afternoon, a practice he adopted later in his life.59 He had arranged with Britain’s counsel-general in Havana for payment for some Cuban cigars that he told Jennie he intended to store in his humidor at 35a Great Cumberland Place, his mother’s London residence that also served as his temporary home.
Thanks to Churchill’s exploits in Cuba and his Daily Graphic articles, he and his friend Reginald Barnes were met by a horde of reporters on their departure from New York for England on December 14, 1895. As he prepared to sail for home, only weeks after being identified merely as his father’s son, Churchill was besieged on the dock by an eager American press to whom the just-twenty-one-year-old gave informed, intelligent answers, emphasizing that he represented no one but himself, and certainly not his government, a claim made a bit difficult to sustain because the Spanish government had gone to great lengths to suggest publicly that Churchill’s presence did indeed demonstrate Britain’s support for Spain.60
The New York World snarkily reported on December 15, “Two young English warriors who have just taken their baptism of fire in the Cuban war set sail for England yesterday on the Cunard steamer Etruria, without a wound and with a conviction that there are few occupations more salubrious than that of a Cuban insurgent…. The young warriors were Winston Leonard Spencer Churchill and R.W.R. Barnes…. they tossed up a penny to see whether they should chase foxes this winter or watch Gen Campos chase rebels…. Churchill is not yet twenty-one years of age” [he had very recently turned twenty-one].61
In an early display of the wit and his tendency to rely on humor to understate the risk he had run, Churchill told reporters, “The most remarkable fact seems to be that the two armies will shoot at each other for hours and no one will get hit.”62 In a follow-up report a few days later, December 19, the New York Herald reported that Churchill had expanded on his quip: “ ‘One conspicuous feature of this war,’ he continued with a merry laugh, ‘is the fact that so few men are killed. There can be no question as to the immense amount of ammunition expended on both sides, but the surprising truth remains that ridiculously little execution is done.’ ”63
Churchill also gave a cogent report of the prospects for both sides, and repeated his jest about the few “executions” despite the “immense amount of ammunition expanded on both sides.”64 He continued this description of a seemingly danger-free adventure much later when he reflected on his Cuba experience. “…I went to Cuba. I did not fight, but wrote about the insurrection. I did not see much of the rebel army—little more than a puff of smoke now and then from some jungle.”65 That vastly understated the reality of his military experience. He had marched, armed with a weapon for self-defense, with troops that were often traversing territory controlled by the rebels. At one point, “suddenly, close at hand, almost in our faces it seemed, a ragged volley rang out from the edge of the forest”; at another, “the air was full of whizzings, and the palm trees smitten by the bullets yielded resounding smacks and thuds…. The bullet had certainly passed within a foot of my head. So at any rate I had been ‘under fire.’ That was something.”66
The New York Herald reporter admired the fact that Churchill, “the pleasant faced young officer arrived at the dock only five minutes before sailing time, and submitted as gracefully to the requests of the waiting group of interviewers as though there were hours of leisure on his hands.”67 Not for the first time, Churchill’s late arrival and insensitivity to the demands of a ticking clock were not new and would remain with him throughout his life, to the fury and anxiety of everyone around him. In Churchill’s pocket as he sailed for home was “a rough insurgent bullet that struck and killed a Spanish soldier…”68
Churchill likely had in mind handing that bullet over to the British director of military intelligence, who had requested a sample as a clue to the weaponry being deployed by the insurgents when he approved Churchill’s mission. He also brought to London some “excellent coffee, cigars and guava jelly to stock the cellars,…,”69 as he had written his mother he would do.
Churchill, who always arranged to remain in contact with people of interest or importance after an initial meeting or correspondence, had a special place in his emerging network for Bourke Cockran. Over the years, they corresponded frequently to discuss shared interests: currencies, free trade, elections and the cost of campaigning, the Boer War, events in the Philippines, and the immense value of the rule of law, among many other policy issues.
The mutual cordiality between Cockran and Churchill should not be mistaken for agreement on important issues. The congressman, regarded as “a maverick politician because of his devotion to principle over party,”70 and his visitor disagreed about Cuba, no surprise since Churchill was at heart a British Tory imperialist and Bourke a leading American liberal Democrat actively supporting the rebels.
In April 1896 Cockran solicited Churchill’s views on a speech he had delivered in which he referred to “Irish suffering” and laid out the case for Cuban independence, both issues on which he differed from his young correspondent, then not yet twenty-two, only a bit more than half Cockran’s age. Churchill’s reply was a model of civility, praising the speech as “one of the finest I have ever read,” and agreeing that “Britain has treated Ireland disgracefully in the past.” But he added, “I consider it unjust to arraign the deeds of earlier times before modern tribunals & [sic] judge by modern standards.”71
Bourke and Churchill did not allow these differences to sour the relationship between them. Both men understood the value of a friendship of equals that allowed for political differences, that, civilly aired, could contribute to better understanding by both parties. This sort of tone, clear, forceful, and civil, set early by both men, would prevail in the extraordinary exchanges of these men for almost three decades, ended only by Cockran’s death in 1923. They were still very much in Churchill’s mind when he delivered his so-called Iron Curtain Speech in Fulton, Missouri, a half-century after he began to trade views with Cockran. Churchill adapted many of Cockran’s oratorical techniques which, added to his own, created a formidable arsenal. Although Churchill had not actually heard any of Cockran’s speeches delivered, he was very familiar with their contents and learned from their structure.72
Churchill’s ability to maintain cordial relations with those of opposing points of view was to stand him in good stead as he went on to construct his American network. He disagreed with the isolationist views of Robert McCormick and William Randolph Hearst, but without surrendering any principles dined amiably with both and benefited from their introductions to important people who favored Churchill’s “unity of the English-Speaking peoples.” He surely did not agree with the diminished role Henry Luce had in mind for Britain, “the American Century,” but secured his support for American aid to Britain without surrendering his own view that the British Empire was a force for good.
This talent was one reflection of the valuable lessons he had learned from Jennie—networks matter, and they do not spring up by chance.