It has to be said that being a participant in government military/strategic circles from a very young age exposed him to the people who were proponents of all those big ideas, as well as having access to classified and scientific information that no ordinary writer or other Futurist would, bitter experience of failure in Mesopotamia in WWI, and other factors that amount more to exposure, experience, and hindsight than foresight. In his own way he was as given to whimsically silly ideas as Nikita Krushchev was in the next epoch, but was allowed the grace to play them out in a time where the consequences developed more slowly and less visibly than in the age of MAD and electronically-interconnected world markets.
Before getting too carried away with the Cult of Churchill, it tempers things a bit to remember the two biggest debacles for which he is pretty much entirely to blame and should also be remembered: Gallipoli in WWI (An irredeemable disaster in every respect, including the empowerment of Islamists) and the Italian Campaign in WWII (Which far from its stated goals, ended up consuming considerably more Allied forces and resources than Axis ones, with a negligible effect on the outcome of the war).
Interesting man that came from an even more interesting family. His Mother has allways interested me, Quite the woman she was. His child hood was surrounded by free thinkers and by the time he set out in his 20's to see the world for itself must have been a surprise to him.
Every thing from the Boxer Rebellion to the Boar Wars, his travels through lands that had open slave markets to the Opemin dens of Asia. Quite the education he received as a young man.
Took a few twists and turns as he returned to his mothers side, High Tea at her house must have been quite interesting.
Like us all he bought into ideas that turned out to be dead ends and off he went to become a world player on the stage of life.
I kind of like the old Dude, he came through for his country in the time of need gathered the strength to put his life on the line.
Interesting as was Ben Franklin that had some odd quirks, The Hell Fire Club and his bringing a known Pedophile to America from France to train our troops for war.
Have to remember in the Civil war the Gentlemen came from the south, did not smoke, drink or Whore about.
The North Had the most outrageous drunkards and carousers in the fight. Sherman and his march to Atlanta and a scorched earth policy, most ungentlemanly from the Souths point of view.
Life is strange, some times it is the meanest SOB that will win a war, and old Winston came out fighting with gloves on. He saw the error of his ways and dropped all alliances with those that tried to harm his country.