Pappy Winchester has kicked the bucket! Poor thing, he was the king of swindlers and everyone knows he was filthy rich! His final wish was that his descendants would share his fortune and the plots of his ranch, with the richest becoming the new head of the family. After all, for him the most important thing was that his money stayed in the family! Pappy thought of everything and left an outline of his belongings. In Pappy Winchester, you and the other heirs are now assembled around this map to divvy up Pappy's possessions...

The game board features 19 plots of land, divided into seven desert plots, six prairie plots, and six forest plots, with train tracks and a river running crossways through the land, and a saloon set apart from everything else. To set up play, give each player $8,000 and two secret objective cards, then place a bonus token face down on each plot of land.

On a turn, the active player draws a plot token at random, then players hold an auction for that plot, with the winner marking it with one of their tokens, then revealing the bonus token and carrying out its effects. This token might let you look at the face-down mine or ranch cards to determine the value of those plots; move the train or boat along the tracks or river, with players owning properties adjacent to this vehicle's location earning money; or collect funds from the saloon. The winner of the auction then divides their bid as equally as possible among all other players, with any remainder being placed on the saloon.

Each player starts the game with a duel token, and when a player is involved in an auction that's down to them and someone else, they can decide to sped that token. If they do, a third player shuffles two duel cards €” one showing a gun being fired, and the other not €” then each bidder takes one of them, with the player holding the firing gun winning the auction.

Five piles of banknotes are laid out at the start of play, with a different shared objective card placed on each pile. If the completion of an auction allows a player to meet one or more of the objectives, such as owning one of each type of land or having three plots that don't touch the river, then that player claims the banknotes under that card. After the 19th auction, players reveal their secret objectives, earning money for how well they've met those goals, and whoever owns the most plots of land receives $5,000. Whoever now holds the most money wins!