Churchill as a Person

Churchill looked after the servants on his estates and his workers and his assistants.
When the work was finished he helped them find other positions.
They liked working for him.
Churchill spent much time socializing, in exchanging ideas, meeting people, hearing opinions, and intellectually sparring in witty conversation.
He frequently imbibed moderate quantities of champagne and brandy but usually was only mildly influenced by it.
He could recite verbally realms and realms of poetry including that expressing ideologies and attitudes opposed to his own.
He could be persuaded to change his mind. For his part, he spent much time writing and sending messages trying to persuade others to change their minds.
He was a long-lived politician. Churchill modified and altered his opinions from time to time being influenced by prevailing trends of thought and different circumstance.
Erstwhile opponents and adversaries could become friends and allies.
Churchill frequently came up with new original ideas for shortening the war. 
Sometimes he was right and at other times he had to be talked out of whatever new notion he had come up with.
Churchill gave people the feeling that they were capable of doing more than they had thought, that they could be more than they imagined. Churchill encouraged others to believe in themselves.
Churchill was a fighter and was prepared if necessary to go down fighting. In his youth he had been a champion fencer and a polo player of world class.
He wrote all, or most, of his own speeches and spent much time preparing them and practising their delivery.
Churchill was born into the aristocracy. He had his prejudices but was also realistic and took people for what they were.
Churchill believed that through his mother he had both some Amerindian and some Afro-American ancestry.
Churchill liked Jews and was liked by them.
 Churchill believed in encouraging innovation and new inventions. He did his best to understand how things worked.
 If an idea (e.g. the battle-tank) appealed to him he backed it, followed its progress, and made sure it came to fruition.
 The founder of his dynasty, John Churchill, had come up from a poverty stricken childhood in the house of a fallen down aristocrat. 
 Arabella, the sister of John, became the mistress to the brother of the king. John himself served as a page and the equivalent of a part-time gigolo.
From this background John Churchill progressed to become one of the greatest military strategists who ever lived.
John Churchill had proven himself and fought to do so. A consciousness of where he had come from was always with Winston Churchill.
Winston Churchill believed in his destiny, in the destiny of Britain, and of the English-speaking peoples.
He inspired others with this belief.
People identified with Churchill. His combination of pugnacity and vulnerability appealed to the public. They could identify with it.