Look at Churchill's speeches or FDR's fireside chats. Now look at Donald Trump's twitter stream
Please. Any historian will tell you that Churchill and Trump had quite some things in common. Your perception is merely coloured by the emphasis of historical retellings, which focus you on very specific parts of Churchill's life and views and ignore all the rest. Trump is in the here and now so you see it all.
Churchill was an incorrigible racist who lost the very first election after the Allied victory, largely because he was seen as an incapable peacetime leader who was obsessed by Empire. He wasn't a popular pick even when he became Prime Minister, due to the perception of incompetence.
If Churchill had a Twitter stream today it'd whip up the mob of the always-offended far faster than anything Trump has done. Here are some Churchill quotes. Imagine them in the Twitter stream of a 21st century politician using contemporary English, who never won a war, and see if it changes anything:
"I like pigs. Dogs look up to us. Cats look down on us. Pigs treat us as equals."
"It is, thank heaven, difficult if not impossible for the modern European to fully appreciate the force which fanaticism exercises among an ignorant, warlike and Oriental population"
"A love for tradition has never weakened a nation, indeed it has strengthened nations in their hour of peril."
"Success is the ability to go from one failure to another with no loss of enthusiasm." (sounds a lot like "WINNING" doesn't it)
"In each case civilisation is confronted with militant Mahommedanism. The forces of progress clash with those of reaction. The religion of blood and war is face to face with that of peace. Luckily the religion of peace is usually the better armed."
"It may be said, therefore, that the military opinion of the world is opposed to those people who cry 'Democratize the army!' and it must be remembered that an army is not a field upon which persons with Utopian ideas may exercise their political theories, but a weapon for the defence of the State." (don't think he'd like women in the army)
"I think a curse should rest on me — because I love this war. I know it's smashing and shattering the lives of thousands every moment — and yet — I can't help it — I enjoy every second of it."
"I am strongly in favour of using poisoned gas against uncivilised tribes. The moral effect should be so good that the loss of life should be reduced to a minimum."
Churchill is rightly remembered as a great man - in war, you need someone who enjoys war and is good at it to defend a nation and only a great man could have beaten Hitler. But let's not pretend he was some sort of ultra-intellectual anti Trump. Put Churchill quotes on Twitter under a pseudonym and he'd be banned within hours.