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Pappy Winchester Board Game Review and Rules

Pappy Winchester Board Game Review and Rules

Pappy Winchester has died. While his death is sad, thankfully he was rich and you are one of his lucky descendants who will inherit some of his wealth. While everyone will get a share of Pappy Winchester’s estate, you want to become the new leader of the family and that can only be done by generating the most wealth with your inheritance. While there have been a few other board games built around trying to maximize your inheritance (there are even games where you try to blow your inheritance), I was intrigued by Pappy Winchester. The premise/theme intrigued me, and I generally like games published by Blue Orange Games as they generally find the right balance between strategy and accessibility. Pappy Winchester is a fun auction game with a few twists that the whole family can enjoy even though it does have a few issues.

How to Play | My Thoughts | Should You Buy? | Comments

How to Play Pappy Winchester


  • Place the game board in the middle of the table. Place the Locomotive on any of the railroad squares and the Boat on any river squares.
  • Randomly place one Bonus Tile on each plot of land.
  • Shuffle the Mine cards and place one face down on each of the Mine spaces. The other cards are returned to the box with none of the players looking at them.
  • Shuffle the Ranch cards and place one card face down on the Ranch space. The rest of the cards are returned to the box with none of the players looking at them.
  • Place one banknote on the Saloon.
  • Place the Plot tokens next to the board face down.
  • Make five piles of banknotes consisting of the following number of bills: (3, 4, 5, 6, 7).
  • Shuffle the Shared Objective cards and randomly place one face up on top of each of the five banknote piles you just created. The rest of the cards are returned to the box.
  • Place the Pistol Duel cards to the side of the game board.
  • Each player is given the following:
    • 8 banknotes
    • 10 Hat tokens in their chosen color
    • 1 Duel token
    • 2 Secret Objective cards. Players can look at these but shouldn’t show them to the other players.
  • The remaining banknotes form the bank.
  • The last player to have watched a Western movie starts the game and gets the First Player token.

Playing the Game

Each turn consists of three phases:

  1. Bidding
  2. Buying A Plot
  3. Verifying Shared Objectives


The player with the First Player token will randomly choose one of the Plot tokens which indicates which property will be put up for auction next. Place the Auction in Progress token on the plot up for auction so everyone can see which property they will be bidding on.

Start Auction in Pappy Winchester

The 18 Plot token was chosen so plot 18 will be auctioned next.

The first player will begin the bidding. Each player can either choose to raise the current bid by at least $1,000 or to pass their turn. Once a player passes, they can not bid later in the current auction. Players can only bid up to the amount of money they have on hand. Players don’t have to show the other players how much money they currently have.

Bidding continues until only one player remains. This player wins the plot. If no one bids on the plot, the first player must purchase it for $1,000.


The one catch to a normal auction is that each player can initiate one duel during the game. When there are only two players left in an auction, one of them can choose to duel for the property. When you choose to duel, you will have to discard your Duel token.

Duel in Pappy Winchester

One of the players has decided to use their Duel token to start a duel with the remaining player in the auction.

The two Pistol Duel cards are shuffled and each player takes one of the cards. The player who gets the Bang! card will win the duel. They will win the auction for the property and will pay the amount of the last bid.

Duel in Pappy Winchester

The player who draws the card on the left will win the duel and get to take the property for the amount that was last bid.

Buying A Plot

After a player has won a property they will pay the amount that they bid on it. The money they bid will be evenly split between the other players. If the bid cannot be evenly split between the other players, the excess money will be placed on the Saloon space.

Win Auction in Pappy Winchester

The player who won the plot of land bid $5,000. As there are three other players in the game, each will receive $1,000. The remaining $2,000 will be placed on the Saloon.

The player that won the plot of land will then place one of their Hat tokens on the space to indicate that they own the property.

The player will then take the Bonus token from the plot and apply its effect (see below).

If the plot contains the Ranch or a Mine, the player will take the corresponding card. They will turn it over and receive the corresponding amount of money from the bank.

Finally the winner will take the First Player token as they will be the first player in the next round.

Bonus Tokens

Token in Pappy Winchester

Movement– When a player gets this token, they will choose either the Locomotive or the Boat. They will have the opportunity to move their chosen vehicle to any of the corresponding spaces (Locomotive has to stay on the tracks, Boat has to stay on the water). A player could also choose to keep their chosen vehicle on its current space. After moving/not moving a vehicle, each plot of land adjacent to the chosen vehicle’s current location will earn $1,000 for the player that owns it. This money is taken from the bank.

Move Train in Pappy Winchester

The train has been moved to this position. The black player will receive $2,000 from the bank as two of their properties touch the train’s current position. The white player will receive $1,000.

The Saloon– The Saloon token allows you to take all of the money from the Saloon space. The money you just put in the Saloon this round is not collected.

Saloon Money in Pappy Winchester

As the player received a Saloon token they will take all of the money currently on the Saloon space.

Bonus Token in Pappy Winchester

Rumor-This token allows you to look at any one card in play. This includes another player’s Secret Objective card, or the Ranch card/Mine cards still on the board.

Verifying Shared Objectives

The players will check the face up Shared Objective cards to see if they completed them. If a player has completed a Shared Objective card they will discard the card and take the corresponding banknotes from underneath the card. A player can complete multiple Shared Objective cards at one time.

Complete Shared Objective in Pappy Winchester

A player has completed this Shared Objective card. They will take the money from underneath the card for their reward.

As long as there are plots that haven’t been purchased yet, another round is played.

Shared Objectives

End of Game

The game ends after the nineteenth round has been played (all of the plots have been auctioned off).

End of Game in Pappy Winchester

All of the plots have been auctioned off so the game will enter the end game.

Players will total their net worth from the following sources:

  • Sum of completed Secret Objective cards
  • Banknotes that they still possess
  • The player with the most plots of land will receive a $5,000 bonus. If two players tie for the most, the player with the most connected plots breaks the tie. If there is still a tie, both players get the $5,000. This money comes from the bank.

The player with the highest net worth wins the game. If there is a tie, the tied player with the most banknotes (not earned from Secret Objectives) wins. If there is still a tie and only one tied player still has their Duel token, they win. Otherwise the tied players share the victory.

Secret Objectives

My Thoughts on Pappy Winchester

On the surface Pappy Winchester seems like your typical bidding/auction game. In many ways it is as the auctions are the main mechanic of the game. The game is mostly built around a plot of land getting put up for auction each round. The auction mechanics aren’t nothing particularly original as player take turns either raising the bid or dropping out. Ultimately whoever bids the most wins outside of the rare duel.

Basically if you have ever played an auction game before you should know what to expect from this element of the game. The auctions don’t really innovate in any significant way, but they are solid enough. If you generally like auction games, you should enjoy this aspect of the game. If you don’t really care for auction games, it may not be your type of game as the gameplay is built around them.

While the auctions are the backbone of the gameplay, they are supported by the fact that all of the players have their own secret objectives. On their own most of the plots don’t have much value. The ranch and mines have cards on them that give you some money. The plots otherwise have Bonus tokens which can also earn you some money. The main reason to acquire plots though are to meet your own secret objectives. The secret objectives can range from acquiring certain types of plots, plots in certain sections of the board, or even plots that help you acquire certain Bonus tokens.

This mechanic is what makes the auction mechanic of Pappy Winchester work. Just bidding on plots to acquire them would be kind of boring. Having secret objectives to complete gives you a goal and makes you have to focus on acquiring certain properties. As you don’t know what the other players’ objectives are, you never quite know if they really need a plot they are bidding on, or if they are just bidding it up in order to force another player to pay more for it. This makes the auction elements considerably more interesting as it becomes more than just acquiring plots just to acquire them. You don’t have enough money to purchase everything so you need to prioritize what you want the most.

There is one last element of the auctions that is not as evident at first glance. In most auction games players’ bids go to the bank. In Pappy Winchester though, the winning bid gets distributed to the other players. This creates some interesting side effects. While you might win a plot, you also indirectly helped out the other players as you increased their wealth with your bid. Thus you need to factor in how much money you are giving the other players whenever you make a bid. If you bid a lot on a plot, the other players will receive almost as much benefit due to now having more money available to them. This gives players more incentive to bid you up and leaving you with the property as they will indirectly receive more money themselves.

I had some conflicted thoughts about this. In some ways I found the mechanic interesting as it really forces you to think about how much you are bidding for a plot. In addition to dropping your own wealth, you are also increasing the other players’ wealth. Thus you need to carefully consider whether the benefit you receive outweighs all of the money you are giving to the other players. This gives you another thing to think about when bidding as sometimes it is better to just pass on a property and take the money from the other player.

This illustrates the main problem that I had with the mechanic as well though. Having to give the money you bid to the other players drives down the prices of auctions which kind of works against the point of an auction game. Outside of rare instances it is usually not a good idea to bid too much to acquire any individual plot. In fact a valid strategy in the game is to barely win any plots. In fact in one three player game a player ended up winning while only acquiring three of the nineteen properties. Some luck was involved, but this illustrates that in many cases bidding more than maybe a couple thousand is not worth it.

The final element of the game involves the duels. The duels don’t play a large role in the game. Each player can only initiate one duel, and you can only start a duel once only two players are left bidding. Basically the only reason to duel in the game is either when you want to limit the amount you will have to pay for a plot or if you think your competition will spend more than you. Otherwise there is no point to use them as you have a 50/50 chance of winning. If you win, you get a good deal. Otherwise you give a good deal to the other player. Ultimately I found the duels to occasionally be a useful tool, but they usually don’t play a large role in the game.

While Pappy Winchester has a few mechanics, I would say the game remains pretty easy to play. I would say that it is a little more complicated than your typical mainstream game, but there really isn’t anything about the game that should be all that difficult even to people that don’t play a lot of board games. The game has a recommended age of 8+ which seems about right. While players might need to reference the rules to see what the various objective cards do, the game can otherwise be taught in around five minutes. The game plays rather quickly as most round only take a couple minutes. Ultimately I would say that Pappy Winchester has the makings of a good gateway game for the auction/bidding genre.

As for strategy no one will confuse it for a highly strategic game, but it has enough to keep most players interested. Most of the strategy comes from the various objective cards and what players ultimately prioritize. You don’t have nearly enough money to buy all of the plots, so you need to prioritize which matter the most to you. You also need to figure out when to give up on a plot and be happy with just taking the other player’s money. It is usually pretty obvious what you should do in most cases, but smart play will allow you to avoid costly mistakes and improve you chances.

Ultimately I enjoyed Pappy Winchester. The game isn’t the deepest, but it does a pretty good job creating a fun little auction game that also has enough unique twists to keep things interesting. While I enjoyed the game, it does have some issues.

Probably the biggest problem with the game is just the fact that the game relies on more luck than it probably should have. Luck actually comes from a number of factors. First the order that the plots go up for sale can make a pretty big difference. If a plot you really want goes up when you don’t have much money left, you are out of luck. Otherwise you could get stuck in a situation where none of the plots you want go up for auction until later in the game. This will make it hard to acquire any of the shared objectives. What properties other players want becomes a big factor as well since you could get the plots you want for cheap as there is no competition. Meanwhile another player might have to pay considerably more as another player really wants it as well.

Probably the most luck comes from the secret objectives. Most of these are mild variants of one another. They reward you with about the same amount of money, and are similarly difficult to meet. There are a couple cards that give you more money though and aren’t much more difficult to acquire. For example with one objective you could acquire $10,000 just from purchasing two plots while another requires you to purchase three and you still have only acquired $9,000. On top of this if you get two objectives that work really well together, you can maximize your value even more.

This reliance on luck is one of the reasons that the player that only acquired three plots in the entire game was able to win. Those three properties earned them a lot of money from their secret objectives. They were then able to just sit back and hoard the money that the other players bid on the other properties. Outside of maybe tweaking some of the objective cards, there isn’t much that the game could have done to reduce the luck. I mostly wanted to bring it up because you need to know going in that luck could play a somewhat significant role in who ultimately wins.

The only other significant complaint that I have with the game is that I think it will play better with more players. The game supports between three and five players. The game is okay with three players, but I think it would be better with more players. Having only three players generally means that only two players are going to bid on most plots and sometimes only one player. This hurts the auction mechanic as the auctions are generally pretty short and kind of anticlimactic. With less players you are even more encouraged to bid less as you will end up sharing more money with the other players. For example if you bid $8,000 on a plot, you will end up giving $4,000 to each player. With four other players you would only be giving each player $2,000. It is hard to justify paying a lot for a property when you lose that money and also give a boost to your competition. While the game is perfectly playable with three players, if possible I would recommend playing with more players.

Finally before wrapping up I wanted to quickly talk about the components. Like most Blue Orange Games titles, I generally really liked the game’s component quality. While they are completely cosmetic and totally unnecessary, I love the addition of the 3D vehicles as they bring a sense of charm to the game. The components are made out of cardboard, but it is pretty thick. The game’s artwork is quite nice and adds to the theme. There is a typo in the rules though regarding the explanation for the secret objective regarding the mines as it doesn’t list the correct spaces that it applies to. Otherwise there really isn’t anything to complain about the components as they live up to the high standards present in most Blue Orange Games products.

Should You Buy Pappy Winchester?

While not perfect I had fun playing Pappy Winchester. At first glance it may seem like your typical auction game as the gameplay is built around auctioning off plots of land. While this doesn’t differ much from your typical auction game, it has some interesting twists that keep things interesting. Each player has secret objectives which help players craft a strategy around what properties to acquire. The fact that the money you bid goes to the other players also forces you to carefully consider how much you bid since if you bid high you might be helping the other players almost as much as you help yourself. The game does a good job making itself a gateway game as it is pretty easy to play and yet has enough strategy to keep most players interested. The game does rely on quite a bit of luck though as the winner could win in part due to having luck on their side. I also would recommend trying to play with at least four players as there are some negatives to playing with only three players.

Ultimately my recommendation for Pappy Winchester comes down to your thoughts on the premise and auction/bidding games in general. If you don’t generally like auction games or don’t find the premise to be all that interesting, I don’t think Pappy Winchester will be for you. If you are looking for a more accessible auction game with some interesting ideas though, I think you will enjoy Pappy Winchester and should consider picking it up.

Buy Pappy Winchester online: Amazon, eBay