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 win the peace and the game.

Churchill is NOT a wargame, but a political conflict of competition and cooperation. While focus of the game is 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 every conference small groups of advisors and senior officials moved between the Allied capitals making the deals that drove the post war peace. Every 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, political activity, clandestine operations, and strategic warfare (A-bomb). Each of the historical conference cards independently places some number of issues such as directed offensives or production priorities metaphorically put on the table, while the players nominate an additional 7 issues.

The game display for this is a circular conference table that three players sit around behind their 'seat'. Each player has a staff deck of named personages, such as Secretary Stimson and Anthony Eden that are randomly drawn to form your conference hand. A pre-conference round of cards will give leverage to the winner who then moves an issue toward their side of the table equal to the value of the card played. Play then proceeds with the conference where every player in turn plays a card on one of the issues in the center of the conference table moving it the value of the card toward his side of the table. Every card is a historical personage and they often have bonuses if played on a particular category of issue. Contesting an issue will have you move an issue away from an Ally toward your own. At all times every player has his Head of State card (Roosevelt, Churchill, or Stalin) that can weigh in on any issue once per conference by discarding another card. Every use of your personage has a bonus and a potential penalty. Every time Roosevelt is used he may die and be replaced by Harry Truman. Churchill can have a heart attack and miss the next conference, while Stalin's paranoia may cause a mini-purge and reduce his side's effectiveness for the remainder of the conference. The net result of this conference play is players will 'win' various issues with the player who won the most issues gaining leverage in one of the bilateral global issues (UK versus USSR global issue is Free Europe versus Spheres of Influence).

The game will then move into a post-conference phase where players implement the issues that they now control. These actions will impact three basic game functions: clandestine operations, political activity, and military offensives. Clandestine operations has players attempt to establish political networks in conquered countries and colonies. Using a very simple mechanic of putting a network or removing an opponent's network, the historical ferment that occurred in Yugoslavia, France and across the world is simply simulated. A country or colony may only have one dominant side's network at any given time, and during political activity players can emplace friendly governments in exile that can be subsequently undermined and replaced if the supporting networks are later neutralized by one of your allies.

Once this has all been done, the military portion of the game keeps the score. There is a separate display that abstractly represents the major theaters of war, Western, Eastern, Mediterranean, Arctic (Murmansk convoys and Scandinavia), CBI, SW Pacific, Central Pacific, and the Far East. Each of these tracks has a Allied front that advances toward Germany, Italy, and Japan. Using a very simple combat mechanic, every front tries to advance with Axis reserves deploying to oppose the various fronts. A successful offensive will advance the front one space, although with overwhelming superiority a two-space breakthrough is possible. Naval operations are simply handled by needing a defined level of support to advance into an amphibious entry space such as France (D-Day). When a front enters Germany, Italy or Japan they surrender, shutting down military operations, although clandestine and political activity will continue until the end of the game. In the background is the development of the A-bomb and Soviet attempts to steal its secrets. If the A-bomb is available Japan can be forced to surrender without a direct invasion.

As stated this is not a wargame, but a three-player excursion into power politics. The game takes around 3 hours to finish, but will be including a short and medium scenario. All scenarios finish with Potsdam, but you will be able to start later in the war if you only have 1 or 2 hours to play. In addition the game can be played with 3 or 2 players plus solitaire.