I am a great fan of Winston Churchill. Otherwise, I would not contribute to this website. However, not many know that while he was a brilliant tactician and a leader, Churchill has lots of flaws. One of the clearest examples of that was his gambling habit.

Churchill growing up

Little Winston saw a lavish lifestyle all around when he was growing up in Blenheim. Not only did his mother like to spend money left and right, his grandfather, a duke tried to make sure that they are living a life of the highest quality.

Not surprisingly, these habits passed on to Churchill and even in school he was known for spending fortunes.

The habit only got worse as he grew up. When he became a member of the Parliament in 1900 he was spending over £100,000 a month in today’s currency equivalent. He started gambling and exchanging stocks. A lot. Churchill took many trips to Monte Carlo where he could lose upwards to £90,000 per trip.

There is actually an amusing quote from one of the Churchill’s losing trips to Monte Carlo: “It excited me so much to play – foolish moth.”.

Stock market did not cover up Churchill’s casino losses. During the Wall Street crash in 1929 Churchill lost a sum that would be equal to £9 million today.

The problem was not gambling itself.

The problem was that Churchill could not control his habits that hurt his everyday life. Even during the time of the World War II as Prime Minister, Churchill missed important meetings due to issues related to his gambling debt.

I am not saying that gambling overall is bad. Some of the best poker games to play can be played for cents and still are exciting as hell.

But Churchill thought he was above the rules of the casino. Not only that he did not have any limits for his games, he also had no restrictions of how much he drank during his time at the casino.

Let me tell you that arrogance and alcohol is a bad combination in a place like Monte Carlo Casino.

Not many historians are willing to admit that but Churchill’s gambling could’ve cost the allies the war.

History repeats itself


But the history did not punish Churchill for his mistakes. An admirer of his bought Churchill out and he lived happily until his death at 90 years old. And here we stand, looking at the present and in it, we see the past.

Yes, I am talking about Donald Trump.

And no, I do not think Trump has even a shred of Churchill’s brilliance.
But again, we have a world leader who, ironically, has his own sad ties with casinos. And we are letting him go unpunished for his words and deeds. On the contrary, all the lies and scams make him more popular.


Mistakes are bad enough. Rewarding our leaders for mistakes they make is destructive to all. That’s why conscious thought and being informed are such important traits in a voter.

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