Okay, I’ll admit that “glorified cheerleader” might be somewhat hyperbolic a term, and also that maintaining resolve and optimism in the populace is important under such circumstances as Britain found itself at the time, but I have always felt, and yet feel, that too much is made of Winston. Partly it’s the way he looked; certainly he didn’t appear to be the type of guy that Americans would consider “leaderly” (could you imagine Winston Churchill in a set of battle fatigues? Absurd!). In the states, where aesthetics have an outsized importance and people are judged by their looks as much as by anything, you not only have to be the real deal, you have to look like the real deal, as well (you know that as well as I do); a fellow like Bill Taft would never be elected president in 21st century America. If you as a man cannot even maintain sufficient personal resolve to maintain your own personal masculinity, then how am I to consider you as my “leader”? I agree that Churchill appeared to be quite adept at doing politics, much in the same way that Tip O’Neill was (a “schmoozer”), but then I would have a hard time considering Tip O’Neill a “great leader” for much the same reason. Simply didn’t look the part. I think that there is a difference between being a “great politician” and a “great leader”.
You say that he “kept Britain in the war” during the Nazi hegemony in Western Europe. How could Britain have done anything other than remain “in the war”, displaying enough ground assets to temporarily deter German thoughts of an amphibious invasion as they were being attacked by aerial bombardment? What type of strategic decisions could Britain have made at the time other than what it did? Without America, there was no hope or question of a Western European invasion of the continent, and America appeared disinclined to involvement. The task for England at the time was to maintain enough population, assets and infrastructure until eventually there was some type of significant change in the status quo: either a “turn of the tide” of the war in the East which would allow Britain to apply the assets that it could in alliance with the Soviets, or somehow convincing American leadership that the Nazi threat was existential. During the interim, there was not much strategic decision to be taken by British leadership, was there? The task for them was to avoid losing too many assets and to maintain the resolve of the British population. “Cheerleading” is a trite term to apply to such a task, but it is not entirely inappropriate, is it? We will never know if Winston Churchill had developed better strategic planning skills than he evidenced during planning of the naval and amphibious campaigns in the Dardanelles in WW1, because he was afforded no opportunity to show that. During the Blitzkrieg, he was “the encourager”, with not many real decisions to be taken, and after American involvement, there were not many decisions for him to take, as most strategic decision making was in American hands.