Probably the most interesting aspect of Churchill's life in politics in the 1930's is how much you can see the hand of the DS in Great Britain before the war. Otherwise, I think they would have been much better prepared to deal with Hitler. Churchill was constantly sounding the alarm about Nazi ambitions, yet the people in power always seemed to side with Hitler while making excuses about how it's best for everyone.
There's just so many parallels to today (and over the past 50 years) it's uncanny. You just have to blur the national boundaries and political parties - it's all there.
How does a guy get into a position where he's responsible for a major military blunder, Gallipoli, tremendous loss of life... Whether or not he was actually responsible and it was actually his subordinates errors, doesn't matter - he was fired and demoted.. But then becomes PM? Where he supposedly fights against communist advances into England, yet when WW2 starts he makes England a strong wartime communist country and allies with Stalin..? I'm a little dry on British history, but did everything just go back to normal after the war or did the DotA have an everlasting impact? All of this without support of the DS? If I'm wrong I'll admit it.
I confess I've always been more interested in world history after WWI, but I know that you have to go back a lot earlier to understand what lead up to the major conflicts.
But as far as Churchill goes, I think he learned from some of his mistakes. He also had a romantic view of the battle field, having fought when muskets were more common, and getting shot at wasn't an automatic death sentence. When WWII started, he needed allies for the survival of GB, and saw a multi-front war with Germany as the best option. He opposed communism, but not at the expense of GB.
Also, he was surrounded by appeasers, who look a lot like DS players. The appeasers were willing to "sacrifice" nations to avoid risking war, knowing that it weaken their own military position. I'm not saying war was the answer, but it seems like everything the appeasers did was designed to either hand over Europe to the Nazis, or put GB on the path towards war and defeat. They did everything possible to weaken the British military for the sake of "the economy". Keep in mind, GB was considered the world power at the time.
I'm not going to try to make excuses for Churchill. I do try to understand what people in historical times faced, what they would have known at the time, and what they were trying to accomplish at the time. He was an aristocrat, and believed in a united nations approach to world politics, along with the survival of the British empire. He opposed Gandhi, but it also seems like he moderated his views somewhat. Does that make him just a politician, or a guy who learns and grows over time?
You are asking good questions, and I don't know enough to delve too deeply into them.
There was a communist party presence in GB during the 1930's, and I'm not sure when Stalin infiltrated the British government. I know he had spies in place during WWII, and that was probably the best time to get them deeply embedded. The US shared nuclear secrets with GB, and Stalin got them from there. GB also shared a lot of secrets with the US (like radar and cryptography).
It's fascinating stuff... I've only met one history teacher that kept my respect, the rest, from junior high to university all peddled the same bullshit.
I have a great friend who studied history in college. If his dad hadn't opposed him following his heart (you need to get a practical education), he would be one of those guys you see on TV adding color to the past. He not only knows the big events and the players, but he's read so many random books about history, that he's picked up a lot of colorful information that makes it come alive.
One time we took a trip to Monticello (Jefferson's place), and while on the tour, we were at the back of the group and I got a better tour than anyone else. My buddy knew details about Jefferson, and the people he associated with (names and dates), that really made the tour. Just one example - Jefferson had a friend (sorry I don't remember the names or dates), who often came to visit, usually brought along a socialite from the DC area, and they stayed in the bedroom that we were touring. Not something you typically read about in the history books about Jefferson.
Might ask him about the invisible connection between England and France during the Revolution... All the text books and eggheads have them as being enemies, but I don't think it was that simple - more likely to me that they were fed instructions and were positioned accordingly to make the whole independence look more real than it was.
BTW, my knowledge of European history after WWII pretty much falls off a cliff.