I wondered about the relationship between General Henry Maitland Wilson and Winston Churchill. After he came to power, Churchill kept calling on a select few men to command. My impression is that they were men he personally knew in some way or at least had grown to have some confidence in them. Henry Maitland Wilson was one of the those, just as Bernard Freyberg was.
It is easy to lose sight of Churchill's military service. He was involved in Africa prior to 1900 and then served in the Great War from early on, at Antwerp, and finished the war. Winston Churchill was both an inspirational leader and a menace. From late 1940 until 1942, we see a lot of Churchill as menace. The later CIGS, Alan Brooke, called Churchill a menace, as he was intimately involved in planning and operations for the latter part of the war. The campaign in Greece was an early example of Churchill as menace. He chose his buddy, Henry Maitland Wilson, to command in Greece. What we saw in Vol.II of the Australian Official History was that General Wilson and his staff were substandard and were the cause of men going into captivity when they should have been withdrawn.
General Wilson is again involved with the Syria and Lebanon campaign. The Australian Official History, Volume II, again makes a case that his judgement and staff work were not what were needed. The Australians had to work hard to compensate for the lack of support that they received from Wilson and his staff. The basic plan for Syria was flawed, in that a short time after the operation began, the Australian General Lavarack was to take over as the commander. The Australians again thought that could have been done prior to the start.
From our knowledge of Churchill as First Lord of the Admiralty, we suspect that he was all about people, relationships, and bold ideas. From June 1940 on to July 1941, we don't see anything to change or minds about him.