Chess is a game that has often been used to draw analogies in libertarian theory. Ayn Rand wrote a letter to Boris Spassky asking several rhetorical questions about what he would do if he were forced to play chess by the same kinds of arbitrary rules as people under his country's government were compelled to abide by in their daily lives. She then stated, "You do not have to answer me, Comrade. You are not free to speak or even to think of such questions--and I know the answers."
Imperial, by Mac Gerdts, is a German-style board game in which the player assumes the role of an international investor buying various countries' bonds. The major investor or investors in a country control that country's government and can direct its production and importation of armaments; building of factories; military maneuvers; taxation; and payment of interest on outstanding bonds. The six countries are, in the original edition, Austria-Hungary, Germany, Italy, the United Kingdom, France, and Russia. In the 2030 edition, they are China, India, Brazil, the United States, the European Union, and Russia. Imperial is fairly popular among libertarian board game players, perhaps in large part because it is one of the few games to feature countries run by investor democracy.
Junta is a satirical board game in which each player is a government official in a corrupt Caribbean island country. The object is to be the player who gets the most foreign aid money into his Swiss bank account by game end. Players use the influence of various voting blocs, such as socialists, bankers, and the church, for rent seeking purposes.
Monopoly is a board game in which the object is to bankrupt all the other players. Key to this strategy is acquiring "monopolies." Many aspects of this game remain inexplicable, such as why, when I own 6 houses and 12 hotels, I would pay rent to stay at my arch-enemy's vacant lot. Furthermore, it makes little sense to pay $2,000 rent at Boardwalk when the much cheaper Mediterranean Avenue is just around the corner. How such a state of affairs can be considered a monopoly when there are so many alternatives available is unclear.
Power Grid is a eurogame in which the object is to build power plants and construct power lines across the country (there are different boards for various nations). The game assumes that rival power companies will not share one another's infrastructure or allow easements, but will instead engage in cutthroat competition. It also assumes that different power companies will not sell their excess electricity to other companies. Electricity is thus deemed by this game to be a natural monopoly.
The prisoner's dilemma teaches that the more one's interactions with another person are likely to occur on an ongoing basis, the more it pays to prove oneself trustworthy and to forgive after exacting retribution (or sometimes, even without exacting retribution). The winning strategy in the prisoner's dilemma is quite different depending on whether the game will be iterated or not. As with most games, a strip version of the iterated prisoner's dilemma is sometimes played as a party game.