Winston Churchill and His Reckless Gambling Addiction

winston churchill gambling image
Winston Churchill Statue. Image Credit: Shutterstock

Besides being one of the most respected statesmen in Britain and globally, Winston Churchill suffered from an unapologetic gambling addiction that followed him his entire life.

We all know Winston Churchill as the great wartime leader of the United Kingdom – a man who singlehandedly said no to Hitler and successfully held out for the duration of the war.  What most of us don’t know, though, is that Churchill suffered from a severe gambling addiction. The famed British Bulldog spent most of his spare time frequenting high-end casinos of London and sinking vast sums of money at roulette and baccarat tables.

It was reported that Churchill would often lose bucketfuls of cash in a single visit, leading to multimillion debt accumulated over the years.  It didn’t help that he was a terrible gambler, which made his gambling escapades that much more fruitless.

Early Years and Manhood

Winston Churchill was born at Blenheim Palace in Oxfordshire on 30 November 1874.  As a descendant of the Duke of Marlborough, he comfortably slipped into the upper echelons of the British aristocracy.  When he reached adolescence, Churchill’s mother dispatched him off to a boarding school.  It was here that his appetite for cash first became apparent, spending more money there than an average six-member family would in a week.

Shortly after he joined the Royal Military Academy at the age of 17, Churchill’s father passed away, an event that further fuelled his excessive spending habits.  As part of his deployment as a cavalry officer, Churchill served in India, Cuba and Sudan, earning him an impressive pay package of more than £100,000 in today’s currency.  In turn, these funds laid the groundwork for his progressively lavish lifestyle.  

After seeing live combat during the Second Anglo-Boer War, Churchill entered the world of politics, rising quickly in ranks to the position of Home Secretary and then the First Lord of the Admiralty.  At the same time as serving in the government, Churchill was regularly seen mingling with other parliamentarians, smoking Cuban cigars, drinking fine cognac and spending big at the horse races and casinos.  This behaviour did not cease even after Churchill became the Prime Minister in 1940.    

An Unrepentant Appetite for Hedonism          

As Winston Churchill’s political stature grew, so too did his alcoholism and gambling addiction.  This led to severe bouts of depression, or his “black dog”, as he termed it.  Nonetheless, the Prime Minister managed to keep his head above the water during the Blitz and the invasion of Normandy.

Churchill’s most infamous gambling incident took place in August 1939, on the eve of the second world war.  At the time, he was vacationing in Monaco, spending his time indulging in excessive alcohol and racking up the largest casino debt he ever made in his life.  Despite his best efforts, he simply couldn’t recoup the losses.  However, with the UK on the verge of war with Germany, he was whisked back to the UK before the casino director could ask him to pay up anything.

History Repeats Itself

By the end of the war in 1945, Anthony Eden was elected as the UK’s new prime minister.  This left Churchill with ample free time and vast sums of money from his biography and published war diaries, allowing him to repay all his debt and regain some normalcy in life.

Shortly after that, Churchill was invited to attend a viticultural event in Monte Carlo. True to form, once the event was over, he embarked on an alcohol-fuelled losing streak at the local casino.  When the casino management asked him to stop playing, he wrote them a cheque for 1,3 million French francs to settle all his previous and current debts.  Out of gratitude for his role in the Allied victory, the casino never cashed this cheque.

The End of an Era

When Winston Churchill died in 1965, the Casino de Monte-Carlo renamed the apartment where he always stayed to “The Churchill”.  He was given a state funeral, and his remains were interred at St Martin’s Church in Bladon.  Throughout his life, Churchill always believed that he was a man of destiny.  Though he lacked restraint when it came to gambling and alcohol, he was fully dedicated to the British people and the fight against fascism.

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