Even after he became a famous writer and military officer, Winston Churchill was constantly overshadowed by his friend Winston Churchill.
The reason the portrait of Winston Churchill looks grumpy on the £5 note, is because the photographer had just snatched the cigar out of Churchill’s mouth.
Winston Churchill had an oxygen mask made for him for flying in high altitude airplanes during WWII that was customized to allow him to smoke cigars through a hole in the mask.
Winston Churchill had a plan called “Operation Unthinkable” to invade the Soviet Union in a surprise attack immediately after the end of WWII. His plan was finally shot down when it was learned that the Soviet troops remaining outnumbered allied troops 3:1.
When the big three leaders of the Allied nations met during WWII, FDR managed to achieve a warm relationship with the rather icy Stalin by making fun of their British counterpart Winston Churchill.