Final answer:
Winston Churchill would most likely agree with President Franklin D. Roosevelt's strategy in Italy as he persuaded Roosevelt to attack through Italy's 'soft underbelly' at the Casablanca Conference before a large-scale cross-Channel invasion into France.
Step-by-step explanation:
The strategy of President Franklin D. Roosevelt in Italy during World War II would most likely be agreed upon by Winston Churchill. At the Casablanca Conference in January 1943, where Roosevelt and Churchill met to discuss European war strategies, Churchill persuaded Roosevelt to move first through Italy, targeting its 'soft underbelly' before considering a full invasion into France. This aligns with Churchill's belief in the strategy of inching towards the core of Axis-controlled Europe through Italy and weakening the opposition before a large-scale cross-Channel invasion.
On the other hand, leaders such as Benito Mussolini, the dictator of Italy during the time of the Allied invasion, Adolf Hitler, the Führer of Nazi Germany, and Neville Chamberlain, who was replaced by Churchill partially due to his policy of appeasement towards Germany's expansion, would not be in favor of this strategy. Mussolini was ousted by the Italian people and briefly reinstated as a puppet ruler by Hitler, clearly positioning him against the Allies. Hitler, eyeing total control over Europe and fighting to maintain his hold over Italy, certainly would not favor an Allied strategy aimed at weakening his control. Chamberlain's previous policies suggest he wouldn't be the most supportive of such military tactics either.
Therefore, based on historical context, Winston Churchill would agree with Roosevelt's strategy in Italy as it was part of their joint war effort, contrasting with the positions of Mussolini, Hitler, and Chamberlain towards the war.