Winston's plan is generally feasible, mainly depending on whether the United States takes the bait. However, based on past circumstances, the British are quite adept at persuading Americans.
During the war, the United Kingdom had a dedicated department for strategies directed at the U.S., hiring numerous professionals familiar with American affairs to lobby the upper class and elites in various fields, promoting the benefits of joining the Allies.
American public opinion was also deeply influenced by the British, which is understandable. At that time, the United States was not the World Overlord as it is known in the future; global opinion domination was firmly in the hands of the British.
