You make some interesting points to answer a few of them -
No it doesn't preclude insight however it can often mean that the gifted writer and orator's opinions are taken more seriously. Also there's the prevailing view of Churchill to take into account in his writing - firstly that after the outbreak of the second world war he was seen as one individual who had been right about european politics (and to be fair he was right) despite facing harsh criticisms for those views during the thirties that has often meant in post war Britain that he has been viewed as being right about many other things when he wasn't. He was undeniably a gifted wartime leader but he was an average peacetime prime minister. His historical writing is significantly dictated by his personality, background and political views all of which would have leant him a more sympathetic view of someone in Nicholas II's position. Personally I find it frequently dodgy and luckily it is merely one of many views and interpretations of history around - to "LIVE" history is no guarantee that you will report it fairly particularly when you have an ego the size of Churchills and were naturally, he was only human, concerned about your own place in history.
I think he naturally felt that Russia's role in WW1 is often overlooked and there are significant historical reasons for it - in the West the collapse of Russia into revolution eventually forcing them out was a bitter blow partially because a two front war was putting enormous pressure on Germany - in those circumstances it is perhaps natural that the men who wrote the initial history of conflict just like Churchill weren't going to give credit to a former ally with an unacceptable government who was seen as having betrayed the allies and to many of those men with only the reports of British and French Ambassadors to go on it was perhaps natural to also place significant blame for that collapse on to Nicholas II's shoulders. Churchill may well have felt he was addressing the deficit with his comment. In the twenties and thirties with a communist government in power again there was little political capital to be made out of looking back at Imperial Russia's contribution to the Great War, in the post war period again Russia was hardly likely to receive credit for her role in the first war though in fairness I don't think her heroic contribution to the second world war is as overlooked.
But a) brilliant oratory does not preclude insight, b) many would not dismiss his comments upon history, much of which he lived, as 'lousy', c) being a monarchist or anti-communist also doesn't preclude insight: on the contrary, such a perspective might countermand the prevailing attitude of the time, which was deeply influenced by the Russian aristocracy's incohesive dispersal across the globe and by the controlled release of documents by Soviet gov't. d) Churchill's role in the Dardanelles was certainly nothing he was proud of, but it would be unfair to forget that his attitude was part of a trenchant view from multiple British generations that they maintain influence over the seas in that part of the world. I agree that Churchill may have felt a tie with N in the defeats they both suffered at that time in history, but I add again that experience can bring insight, not necessarily prejudice. For example, if you removed the chapters discussing hemophilia/parenting hemophiliacs out of Massie's Nicholas and Alexandra, would you not have a far inferior book?
So I feel that World War I did contribute some to the start of the Revolution, so IMO you have to factor that in, which Churchill didn't. Just my views.
And Imperial Angel, I agree with what you said, but I was wondering what people thought about Churchill's comment as he phrases it. I suppose that you are saying that he limited his examples to ones that prove his point. But he does say that N was neither a great prince nor a great soldier, so he might agree with us more than we realize, if only we could sit down and chat with him.
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