The players in the game take on the roles of Churchill, Roosevelt, or Stalin as they maneuver against each other over the course of 10 Conferences that determine who will lead the Allied forces, where those forces will be deployed, and how the Axis will be defeated. The player whose forces collectively have greater control over the surrendered Axis powers will win the peace and the game.

Churchill is NOT a wargame, but a political conflict of cooperation and competition. While the game focuses on 10 of the historical conferences from 1943 till the end of the war these and much of this design should not be taken literally. Before and after each conference small groups of advisors and senior officials moved between the Allied capitals making the deals that drove the post war peace. Each conference sees one of a group of issues nominated for inclusion in the conference. The issues categories are: Theater leadership changes, directed offensives, production priorities, clandestine operations, political activity, and strategic warfare (A-bomb). Each of the historical conference cards independently puts some number of issues such as directed offensives or production priorities metaphorically put on the table, while the players nominate an additional 7 issues.