Despite personifying Britain's defiance of the Nazis during the Second World War, Winston Churchill burst into tears dozens of times during that conflict. To an extent that was truly extraordinary in someovene responsible for the overall direction of British forces. But Churchill was a profoundly emotional man, far more than any of his War Cabinet colleagues. Aged 65 when he became prime minister for the first time, one might have imagined that "the passion of former days", as he was later to call it, would have cooled in him, to be replaced by a calmer analytical reasoning. But in fact the opposite seems to have been the case. If anything, Churchill became more emotional the older he got.

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This can be measured in the number of times that contemporaries noted that he dissolved into tears. Of course WW2, with what he called the “climacterics” of the evacuation from Dunkirk, the Battle of Britain, the Blitz, D-Day, VE-Day and so on, was an emotional time for most Britons. Yet it was their leader who, despite being born at the height of the late Victorian phenomenon of the stiff upper-lip, and into the upper class that was supposed to exemplify it best, was constantly crying in public, and fully deserved Edward VIII and Wallis Simpson’s nickname for him: ‘Cry-Baby’.

While researching my new cradle-to-grave biography, Churchill: Walking with Destiny, I started to count up the number of times that he wept in his life, but stopped when I quickly reached 50. The phenomenon of a national leader crying regularly in public would be an unnerving one today, yet Churchill cried at a time of continuous national peril and in an era when controlling one's emotions was considered almost a prerequisite for leadership. Despite this, the country was fortunate that, in its most perilous moments, it was led by someone who was not a cold, calculating logician who might well have concluded in 1940 that Britain's best course would have been to negotiate peace with Adolf Hitler.

The phenomenon of a national leader crying regularly in public would be an unnerving one today, yet Churchill cried at a time of continuous national peril

In 1993 Churchill’s last private secretary, Sir Anthony Montague Browne, recalled Churchill telling him: “I blubber an awful lot, you know. You have to get used to it.” Montague Browne said that these tears would flow as a result of “tales of heroism. He loved animals; a noble dog struggling through the snow to his master would inspire tears. It was touching.” Montague Browne did not become Churchill’s private secretary until after the war, and Churchill had certainly “blubbed” a good deal before then.

His earliest recorded adult tears came in 1897, on seeing the corpse of his friend Lieutenant William Browne-Clayton, who had been, as Churchill told his mother Lady Randolph Churchill, in a letter, “literally cut to pieces on a stretcher” during the Malakand Field Force expedition in north-west India. He also cried when he witnessed the relief of the besieged town of Ladysmith during the Boer War in 1900, and on the departure of General Sir Henry Wilson, the sub chief of staff to the British Expeditionary Force, for France in 1914.

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Another seven years were to pass before Churchill was recorded to have wept again, at a memorial service at the military cemetery in Jerusalem in 1921, and then again that year at the funeral of his faithful manservant Thomas Walden. These instances were few and far between, and all occasioned by more powerful impulses than the sight of a noble dog struggling through snow, but in March 1924 he cried when he lost a byelection in the Abbey division of Westminster by only 43 votes. He later told his doctor, Lord Moran, that his chronic lachrymosity all stemmed from that moment. But did it?

It is more likely that Churchill’s waterworks sprung from the fact that he was essentially a Regency aristocrat, born out of his time into the emotionally repressed Victorian era where one’s commitment to British imperial duty was equated with not betraying one’s true feelings in public. Of the eight admirals who carried Nelson’s coffin in St Paul’s Cathedral at his funeral in 1806, all were in tears. Churchill emotionally hailed from that earlier age when officers wore their hearts on their brocaded sleeves. His lachrymosity was in fact intimately bound up with his personality rather than explicable through a byelection result, however politically traumatic.

Later in 1924, Churchill cried again when Stanley Baldwin unexpectedly offered him the chancellorship of the Exchequer, the post that his father, Lord Randolph Churchill, had once held. It would allow him to wear his father’s robes, which had been carefully preserved by his mother for just such an eventuality, thereby connecting him to the man whose approbation he had always been desperate to have, but never got anywhere near winning. So this blubbering, too, was perfectly understandable.

Churchill’s wilderness years, when he was out of office in the 1930s, saw him in tears much more than before. He cried regularly at funerals – such as that of his best friend, FE Smith, Lord Birkenhead in 1930, and of Lawrence of Arabia in 1935 – and at weddings, such as that of Prince George, Duke of Kent, to Princess Marina of Greece in 1934. Churchill’s son-in-law Vic Oliver noted how at Chartwell during this period: “When he spoke of family or country with special feeling, there would be tears, unashamed, in his eyes.” There were tears when the Labour politician JH Thomas was forced to resign in 1936 and during the abdication crisis later that same year, as well as during the 1937 coronation of George VI. The Labour leader Clement Attlee recalled “the tears pouring down his cheeks one day before the war in the House of Commons, when he was telling me what was being done to the Jews in Germany”. The Munich crisis reduced Churchill to tears at one point, too.

Churchill’s lachrymosity was building up towards its chronic stage, and was remarkable considering how much public displays of emotion tended to be despised by his contemporaries. It allows us an insight into how extraordinarily different he was from them, and how this grandson of a Victorian duke frankly could not care less what other people thought of him. His extraordinary self-possession, the result of his having been born into the apex of the social order of a country that ruled a quarter of the world, goes a long way towards explaining how he could take such lonely positions on Nazism before the Second World War, and communism after it. Far from showing weakness, his willingness to be seen crying in public actually showed a deep internal strength.

His waterworks sprung from the fact that he was essentially a Regency aristocrat born out of his time into an era where commitment to imperial duty was equated with not betraying one’s true feelings

Once war broke out, Churchill shed tears of happiness when he told his wife, Clementine, that he had been appointed First Lord of the Admiralty, the same job that he had had on the outbreak of the Great War. Even reading Neville Chamberlain’s telegrams to Washington rejecting the idea of the Americans brokering a peace with Hitler could make Churchill cry. When he became prime minister, Churchill famously offered “nothing but blood, toil, tears and sweat”, and the third of these were evident later in that same debate when Churchill’s long-standing friend David Lloyd George commended his premiership to the Commons.

Over the coming months he cried when bidding farewell to Paul Reynaud, the French prime minister, the day before the fall of Paris, and when he was applauded in the Commons three weeks later for sinking the French fleet at Oran. “A sudden passage of pathos or a mention of disaster while dictating a speech would bring the tears to his eyes,” recorded one of his secretaries, “sometimes he would be almost sobbing, with tears running down his cheeks at the end of an affecting period.” He could thus work himself up into a passion while crafting the speeches that later had such a powerful effect on maintaining morale during the darkest times of the war.

In total contrast to Adolf Hitler, Churchill visited bombed out streets and communities throughout the war, where the bravery of the people he met often reduced him to tears. Visiting an air-raid shelter where 40 people had been killed the East End of London in September 1940, he “broke down completely”. “You see, he really cares,” a woman called out, “he’s crying.” Far from damaging his popularity in a society that was far more buttoned-up than today’s, his emotional responses to people’s suffering helped him win Gallup Poll approval ratings of 88 per cent and above for most of 1940. Nor did Churchill’s chronic lachrymosity lower him in his colleagues’ eyes.

Watching movies at Chequers often brought on tears, and on one occasion in 1941 Lady Diana Cooper wrote to her son, the late John Julius Norwich to say: "Winston managed to cry through all of them, including the comedy." In March 1941 there were even tears in Churchill's eyes when he met Mamoru Shigemitsu, the Japanese ambassador. Nor was this anything to do with the supposed depression that Dr Anthony Storr diagnosed in Churchill in his famous book, Churchill's Black Dog and Other Phenomena of the Human Mind. Churchill was not a depressive in the normally accepted sense of the term; it was a mis-diagnosis. He got depressed about things that would have depressed anyone, but his tears were almost never in response to defeats, when the most he ever showed was a defiant growl.

Far from damaging his popularity, Churchill’s emotional responses to people’s suffering helped him win Gallup Poll approval ratings of 88 per cent and above for most of 1940

When Churchill visited bomb-damaged Plymouth in May 1941, Tom Harrisson of the Mass-Observation movement saw “great tears of angry sorrow in his eyes. He was so visibly moved by the suffering that he saw.” More tears of anger were shed in the bomb-damaged chamber of the House of Commons that month, which he made no attempt to wipe away. An account of the sufferings of occupied France moved Churchill to tears the following month, but they were used to good effect in redoubling his determination to make Hitler and the Nazis pay for what they were doing.

Allies were impressed with Churchill's lachrymosity, which is mentioned in the diaries and correspondence of several of the Americans who worked with him during the war. He wept while singing O God Our Hope in Ages Past beside President Roosevelt on board HMS Prince of Wales in August 1941, and four months later when he heard the news of its sinking off Malaya. Yet even something as mundane as a lunch with lobby journalists in March 1942 could set Churchill off. That October, he was also moved to tears during a cabinet meeting by a speech from Jan Christian Smuts, the prime minister of South Africa.

March-pasts, visiting submarines and dying friends, the cheers of the Commons, receiving the freedom of the City of Paris at the Hotel de Ville after its liberation in 1944: all had him in tears.

Some critics, such as the Tory MP Henry ‘Chips’ Channon, privately accused Churchill of using this unusual capacity to weep virtually at will as a political weapon. He noted that Churchill sometimes seemed to be crying for the cameras, as at Roosevelt’s memorial service at St Paul’s Cathedral in April 1945. This was too cynical an interpretation; if Churchill took out his large white handkerchiefs to wipe away the tears, he was accused of drawing attention to them, yet if he didn’t, he was also accused of the same thing.

The Chiefs of Staff Committee quickly got used to Churchill’s lachrymosity, and almost became inured to it as a means of his getting his way. Sometimes the intransigent manner with which General Sir Alan Brooke, the chairman of the Chiefs of Staff, would block his ideas would reduce him to tears of sheer frustration, but he never once overruled the committee when they were unanimous about an issue, which was most of the time. At a victory party soon after VE Day, tears poured down Churchill’s cheeks, as they also did when the news came through of his defeat in the 1945 general election. When in November 1945 King George VI offered Churchill the Order of Merit, Sir Alan ‘Tommy’ Lascelles, the king’s private secretary, noted how he “wept a little, as he so easily does when deeply moved”.

For two-thirds of a century, Churchill had squared the circle of showing superb physical and moral courage, while also weeping on an extraordinary number of public occasions

The older Churchill got, the more he wept, and nor did it take such powerful stimuli as during the war. Prime minister once more in 1951, he disembarked from a train in Ottawa and started crying as soon as the Royal Canadian Air Force band struck up Rule, Britannia. In a debate that December, in which he had commended Clement Attlee for his patriotic efforts over conscription, the atomic bomb and rearmament, the future prime minster Harold Macmillan recorded that there were "tears in his eyes". Churchill's granddaughter Edwina Sandys recalls him crying when he recited poetry, including Macaulay's Lays of Ancient Rome at his country house, Chartwell, in the 1950s.

The death of George VI in February 1952 had the expected effect. “When I went to the prime minister’s bedroom he was sitting alone with tears in his eyes,” wrote his private secretary Jock Colville. The prime minister went to Heathrow to meet the new Queen, and took his secretary, Jane Portal – now Lady Williams of Elvel – to whom he was dictating in the car, who today recalls how he was in a flood of tears for much of the journey. He later broke down crying when rehearsing his speech about the king that he was going to deliver to the Commons. Jane’s son, Justin Welby, the present archbishop of Canterbury, remembers Churchill being in tears when he visited Number 10 Downing Street as a boy.

It took less and less to set Churchill off by the 1950s. He cried during the memorial service of Sir Stafford Cripps in April 1952, despite never much liking him. When his daughter Sarah Churchill reminded him how he had told her back in 1922 that she needed to grow up, “I looked up to him and to my surprise found his eyes bright with tears”. The only surprise is that she was surprised. When he rang Ava, Lady Waverley to console her on the death of her second husband, the former home secretary Sir John Anderson, he ended up shedding tears when recalling the death of her first husband, his friend Ralph Wigram.

One of the drawbacks of living to be 90 was that almost all his friends and contemporaries predeceased him, and he cried at the deaths of all of them, especially the scientific advisor Professor Frederick Lindemann. Upon hearing the news of former minister of information Brendan Bracken’s death from oesophagal cancer, Churchill wept, saying: “Poor, dear Brendan.” There are reports that he also cried on hearing the news of President Kennedy’s assassination in November 1963, and he certainly did on his own 90th birthday in 1964.

For two-thirds of a century, therefore, Churchill had somehow managed to square the circle of showing superb physical and moral courage, demonstrating a determination to endure anything, while also being seen weeping on an extraordinary number of public occasions. He might have been a ‘Cry-Baby’, but the British people preferred to be led by a man who showed his emotions rather than one driven by cold, impersonal rationality.

Andrew Roberts is a visiting professor at the War Studies department of King's College London and the author of Churchill: Walking with Destiny (Allen Lane, October 2018)

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This article was first published in the November 2018 edition of BBC History Magazine

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