At the end of 1135, Henry I, King of England, died unexpectedly without a male heir to succeed him. His daughter, Empress Matilda, considered herself the rightful heir. But the deceased king's favorite nephew, Stephen of Blois, was quicker and, with the help of his brother, the Bishop of Winchester, had himself crowned king. Matilda's supporters refused to accept Stephen's rule, leading to a civil war that plunged England into chaos for eighteen years. This conflict became known as The Anarchy .

In The Anarchy, players take on the role of English nobles loyal to King Stephen. Over five rounds, they build up their domain, defend their castle against the advancing Angevin armies, and storm strongholds loyal to Matilda with homemade siege weapons. The player who musters the most courage, loyalty, influence, and strength, while avoiding discontent, proves to be Stephen's most loyal ally and receives his greatest earldom at the end of the game.