Italy wasn’t so much his preferred ‘soft belly’ (I’m not sure he ever said ‘soft underbelly’, not least because there is a redundancy in that expression which conflicts with his usually precise English) into Europe as the necessary target for available forces to pacify Stalin’s pressure for an invasion before the Western Allies were ready for the big one in Normandy.
His world view was certainly imperial, but he was a child of the Victorian age when the Empire was at its all-powerful and wealthy peak. It was as hard for him to come to grips with a new world as it is for Americans to recognise America’s waning power after the end of the American century.
His inspirational leadership, which inspired both his nation and the American supporters he needed to support his and Britain’s dogged determination against Germany, was the greatest gift he gave to his nation and the free world.
I wouldn’t go so far as to say it excused some of his egregious military blunders such as Greece and Singapore in WWII when he went against competent military advice. I’d say only that those blunders are outweighed by the positives which came from his inspirational leadership outside military strategy.
As for Gallipoli, it turned out to be a stuff-up which was a good rehearsal for even bigger Churchillian stuff-ups in Greece and Malaya / Singapore in WWII but, of the three, Gallipoli had the best prospects of success for Churchill’s forces. But for the excellent leadership, tactics and quick response of the Turkish forces under Kemal (later Kemal Ataturk), it might well have succeeded.
