It’s easy to be constantly confused by history’s timeline, where two random events can seem so far apart yet be so close together. Consider this: Winston Churchill, born in 1874, was fourteen years old when Jack the Ripper started his killing spree in London.
Winston Churchill remains one of the most towering and complex figures in modern history. While his extraordinary leadership in World War II marked him out, the story of his greatness is inextricably linked to his deep flaws and numerous political mistakes.
He was a decent and honourable man, as well as a charming one, and it was these qualities, alongside his famous defiance, that ultimately enabled him to lead a nation. However, he had views on slavery that appear very outdated when we examine them today.
Character and Home Life
Churchill came of age in the late Victorian era, a descendant of the Duke of Marlborough, and developed a set of unconventional habits that defined his supreme comfort with his sometimes strange personality.
He had very unconventional work habits. He was a notorious insomniac and often held important meetings late into the night. The result was a demanding, unconventional work schedule which affected his health, especially as he grew older.
People were not only called upon to take notes in the night but he had a habit of dictating to his secretary whilst lying in bed or in the bath. Many a meeting and memo were constructed whilst Churchill soaked. So obsessed was he with having a bath he installed them everywhere, even on the train he travelled on around England.
In The Splendid and the Vile, Erik Larson tells a story that when President Roosevelt went to talk to Churchill in America, he found him answering the door naked before quickly throwing on a towel to hold the meeting. He discussed the American contribution to World War II in little more than a towel.
When he did get dressed, it was often in a colourful and gaudy dressing gown, every outfit completed with his ever-present cigar in his mouth.
A Volatile Family Dynamic
His demanding life placed strain on his family, yet he relied deeply on them. The only person who was ever said to truly challenge Churchill was his wife, Clementine.
Clementine was a fierce confidant and stabilising influence in his life; she was also his biggest critic. Many a time Clementine was called upon to entertain powerful figures from the war effort. She was a remarkable woman who managed the stresses of wartime life whilst keeping her husband in check.
His children were also a source of comfort to him, none more so than his daughter Mary. Despite Churchill trying to shield her from the war, she was as determined as her father to be of use and helped out during the Blitz, causing Churchill to constantly worry about her.
In contrast, he had a turbulent relationship with his son, Randolph. (Randolph is the subject of our article on Monday.) Randolph disappointed him greatly with his gambling and womanising. However, Churchill remained loyal to him until the end.
A Flawed Political Journey
Churchill’s long political life, which saw him first become a government minister in 1908 and continued to occupy most of the top jobs in politics during half a century, was littered with huge, consequential errors. His historical works would later consciously shape our view of him, though the truth, as always, was more complex.
In Gallipoli, he was instrumental in a disastrous campaign. He supported the Black and Tans in Ireland and backed the use of poison gas in a general sense. More specifically, as Secretary of State for Air and War in 1919, he planned and executed a sustained chemical attack against Bolshevik-held villages in the Russian Civil War. Although, reports differ and some state this was only mustard gas the effects were devastating.
As Chancellor of the Exchequer, he was inexperienced, but in the 1920s he put Britain back onto the gold standard. However, his policies were flawed and John Maynard Keynes, the great economist, believed this was a major factor in bringing about the Great Depression.
His racist views have been highlighted recently; he was an angry opponent of Indian nationalism, and his language about Gandhi verged on racist.
He was also a stubborn supporter of Edward VIII during the Abdication Crisis of 1936. Strangely, going on to be one of the greatest advisors to the young Queen Elizabeth II. As her first Prime Minister, he was also one of her favourites.
The War Years
After years of controversy, the 1930s found Churchill in the political wilderness. He was not to be beaten, and rather than wallowing, he became a one-man media company. Between 1931 and 1939, Winston Churchill published 11 books, more than 400 articles, and delivered more than 350 speeches.
Crucially, it also gave him time for observation. He had visited Hitler’s Germany and seen for himself the potential for evil there. He often had a problem selling his articles about the evils of Nazism to the press because few people, either in the UK or the US, wanted to know. However, these observations would serve Britain well in the future.
Even as war loomed, the most likely outcome was that British Prime Minister Neville Chamberlain would do a deal with Hitler and stand aside. Even after war broke out in September 1939, and Hitler smashed his way through Western Europe, Churchill remained utterly faithful to Chamberlain. He forbade his supporters from leaking hostile stories to the press.
However, Chamberlain couldn’t keep Churchill out of the Cabinet, and he was back at the centre of power as First Lord of the Admiralty. Over time Chamberlain’s policies started to crumble, and he was forced to resign. He put Churchill forward as his replacement.
Churchill was an inspiring leader; he became deeply immersed in all the details and technicalities. He installed key men he trusted in key positions to keep the war effort moving forward. He knew the huge task ahead of him with the lack of aircraft.
His famous speech has an end line that many did not hear: “We shall fight on the beaches...” ended with the line: “and we will fight them with broken bottles cause that’s all we’ve got.”
He was bold with his decisions, brave, and tireless. The speeches he made and his presence at bomb sites inspired a nervous and hesitant Britain to defy the stark odds and horrific destruction to never give in.
Leadership and Personal Resolve
During the darkest days of the Blitz, he used entertaining as a tool to bolster morale and manage relations with allies like President Roosevelt’s envoy, Harry Hopkins. He not only taught his family to be fearless, but also the nation.
He would often climb onto the roof at 10 Downing Street to watch the bombs fall. Despite numerous people trying to get him into the bunkers, he had a stubborn personal need to share the danger with his people. This personal demonstration of resolve was central to his ability to galvanise the nation.
But he was not just a fearless leader; he was a man who had profound empathy and emotional sensitivity when it came to his people. After visiting the heavily bombed city of Bristol, he was seen raising a newspaper to mask his tears, remarking on the courage and “confidence” of the people.
One of the most human stories from the war involves Churchill and the difficult decision to ration tea. He believed, like many, that it was a substance that maintained the British spirit. By rationing it, he reasoned, he would be alienating the working class, especially the backbone of any house: the women.
Women, he said, were holding the fort while their husbands fought the Nazis. They were comforting others during the Blitz and keeping Britain running. After much thought, he decided he would have to ration the UK’s preferred drink, but he made the rations as generous as he could to mitigate the loss.
The Enduring Figure
Churchill’s personality, determination, and refusal to back down are the reasons that I am not writing this article in German. The fight against the Nazis took its toll on the great man. After the war, Churchill was old and ill. Ironically, he was also not elected during the first general election after the war.
Yet he returned to lead the government from 1951–55, refusing for a long time to stand down. He finally retired in 1955, having served as prime minister for a total of nine years.
He became a prolific writer, and his historical works were so good that they earned him the Nobel Prize for Literature.
After the war, he was offered a Dukedom by Queen Elizabeth II, which he refused. He stated he was moved and honoured, but he wanted to die as Winston Churchill and not as anyone else.
He remained an MP almost until the end of his life, leaving Parliament in 1964 and dying in 1965. The historian Sir Arthur noted that no other British prime minister could remotely match the scope of Churchill’s achievement.
Monday we will look at Churchill’s son, a man who struggled to live up to his father’s legacy.
Until next Wednesday: Stay safe, stay curious, and beware the shadows of the past.



He had his purpose and served it well when the time came.
" Between 1931 and 1939, Winston Churchill published 11 books, more than 400 articles, and delivered more than 350 speeches."
To say nothing of the books he wrote before and after that. The most ambitious by far was "A History Of The English-Speaking Peoples", a multi-volume set he wrote and published in his 80s.