Churchill is beloved as the wartime prime minister that provided strong, unflinching leadership to the UK at its lowest point of recent memory. He did this a number of ways:

1. Supremely gifted oration - excellent command of both the spoken and written language
2. Early advocate for action against Hitler and not appeasing him
3. Showed courage by staying in London during the Battle of Britain, aka "the Blitz". His strength of character was something the UK could look to and rely upon
4. Instrumental in developing relations with the USA in the early 40s (before they officially joined the war) resulting in the supply of consumer goods and materials the UK desperately needed
5. Commanded the respect of Stalin, and was pivotal in ensuring that the UK, USA, and USSR worked together to win the war

The views on some of these points, particularly #2, have changed over the years. At a time when everybody was still reeling from WW1 his call to arms against Hitler was initially not well received. As is often the case, with the benefit of hindsight this has been seen as one of his positives.

Churchill is often bemoaned for some of the following issues:

1. Being blunt and or rude - he was rather fond of drink and has been recorded on several occasions being rather serpent tongued as a result
2. Failings as a strategist in WW1 - Churchill was first lord of the admiralty of the navy in WW1 and was behind the disastrous Gallipoli offensive of 1915
3. Domestic governance - He bungled union and labour disputes, as well as had some harsh treatment of antigovernmental activists early in his career
4. Traditionalist - Churchill was an aristocrat born in the 19th century (his family home Blenheim Palace is stunning). His traditional, conservative views did not hold up well against the many cultural and political changes born out of WWs 1+2. He was against Indian and Irish independence and bigoted against both populations (particularly of Indians), supported King Edward VIII when he abdicated the throne (enough material there for its own post), vehemently and openly criticized socialism and new political change

Basically he was stubborn, self-confident, and a bigot. His steadfastness in WW2 combined with his masterful oration allowed him to become bigger than life. When juxtaposed with the changes that were taking place all around him, he was a figure unwilling to change or adjust.

His racial views are particularly damning. We must remember he was born into a society and social class who most likely all held these views, but still he was rather outspoken about it and didn't refrain from letting his personal views go public which doesn't bode well for a national leader.

We owe him a great debt of gratitude for being a lynchpin in defeating Nazism. He was the only person capable at the time of stepping in and leading that charge, but mostly everything he touched before and after WW2 is marred in controversy, ineffectiveness, and out dated conservative imperialism.