This is a rather excellent piece by Joseph Fouche. I recommend reading in full, as illustrates something rather important about strategy–what we understand as iron rules of strategy can sometimes be misleading. Fouche’s basic thesis is that by all accounts, Winston Churchill broke all of the rules of strategy because (in effect), he did not have one:
“Churchill’s strategy in 1940-1941 is vastly different from the strategy most contemporary strategic theorists hold up as an ideal. His strategy was the triumph of hope over experience, one of the great fantasy spectacles of the 20th century. His soldiers were tired, his people were dispirited, his aircraft carriers carried biplanes, his generals were mulish, and his empire was restive. The only anchors in reality for Churchill’s strategy was the inability of Nazis to march over or part the English Channel and American reluctance to see faltering Britain replaced by revanchist Germany. All else was theater. … Churchill’s strategy in World War II consisted of holding on to a series of deluded and contradictory beliefs about the British Empire and its place in the world in the hope that something would turn up.”
Fouche wisely observes that “his appeal to the power of grand narrative was in some ways more successful than orthodox strategic theory can capture or even comprehend. More often than not, the strength of conviction behind a strategy’s more tenuous elements is more important than the tenuous reality warrants.” I’d extend this farther beyond just an explanation of Churchill.
There are many points in military history and current military operations where, by all rules of strategy, one group should have lost for violating some iron principle of war. Unity of command, a lack of a strategic endstate, poor tactics, or inferior weaponry are not necessarily in and of themselves dealbreakers. It will vary by situation and by adversary. Sometimes in the case of Churchill a strong personality can be enough to hold a muddled mass together.