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Some time after him
I am the son of Martin Long, the founder of Churchill insurance. I asked him this question and he responded with the answer that he enjoyed reading about the life of Sir Winston Churchill ever since he was about 10 and decided to devote the name of his company to him. <><><> "The current Churchill mascot was the product of a staff competition designed to identify ways to differentiate the Churchill brand from Winston Churchill." -Wikipedia I'm pretty sure it was not.
This is not actually Canadian, it's a British crown. These sell for about a dollar.
£200
Winston Churchill must have been rich if he could afford the equipment to use during the war and 1939
Winston Churchill was a prolific author so he didn't have much time for hobbies but he enjoyed landscape painting.
Winston Churchill
"Never have so many owed so much to so few"
These are not "coin of the realm", but are more of an investment. At the very least, they will be worth the current bullion value of gold, which is most likely much more than you paid for them.
Never in the field of human conflict has so much been owed by so many to so few. (Winston Churchill) This is not the end, it is not even the beginning of the end, but it might be the end of the beginning. (Winston Churchill)
$10
Winston Churchill.