Red Dead Redemption 2 Gambler Challenge Guide


Red Dead Redemption 2's story mode features many optional challenges, grouped into different categories, which put players' knowledge regarding many of the game's most important mechanics, such as hunting, crafting, shooting and so on, to test. Completing these challenges will allow you to obtain some additional money as well as special equipment that grants bonuses for Health, Stamina and Dead Eye. To enjoy the bonuses, the full equipment set has to be acquired.

All the categories - BanditExplorerGamblerHerbalistHorsemanMaster HunterSharpshooter, Survivalist, and Weapons Expert - include ten different challenges which must be completed in the order they are unlocked. For this reason, progress made toward the completion of a later challenge will not count until that challenge is unlocked.

In this guide, we look at the Gambler challenges and tell you how to complete all of them with ease. Just make sure to have plenty of money with you before attempting to complete them, as it will definitely be needed.

Gambler Challenges Overview

Gambler challenges are related to the mini-games included in the story mode - Blackjack, Dominoes, Five Finger Fillet and Poker. As money is needed to play all of them, you will need quite a bit of cash to complete these challenges: most of the story mode mini-games are luck based, so you will end up playing any of these games over and over trying to complete some of these tasks. Being dependant on luck so much, some of these challenges may drive you mad with frustration, so make sure to come armed with plenty of patience as well.

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Win Five Hands Of Poker

The first Gambler challenge is pretty straightforward, as you must win five hands of poker to clear it. Poker in Red Dead Redemption 2 is based off Texas Hold'Em, so to win a round, players need to have the highest hand using the combination of their own hole cards and the five community cards. Poker can be played at the Van der Linde camp, in Valentine, Tumbleweed, Blackwater, and at Flatneck Station.

As poker is entirely luck-based, there's no way to make completing this challenge any easier, as you not only need to have a good hand, but it also has to be better than the other players'. Things are made even harder by the fact that you obviously cannot bluff nor read other players' intentions. The five hands, luckily, must not be won consecutively, so, with a bit of perseverance, you will complete this challenge without too many problems.

The reward for completing this challenge is the Gambler Holster, which grants a Stamina bonus once the whole set has been obtained.

In Blackjack, Double Down and Win the Hand Five Times

The second Gambler challenge is just as straightforward as the first, as you only need to win the hand in Blackjack five times after doubling down.

Blackjack is the second card mini-game available in the Red Dead Redemption 2. It is much simpler than poker: to win the round, you must have the cards that are dealt to you add up to 21, or as close as possible. Blackjack is played against the dealer, so there are fewer variables involved than in poker.

Once a round has been won, the player has the chance to double down, which is doubling the original bet and continue playing. As Blackjack is entirely luck-based, you may end up spending a lot of money to win after doubling down five times. The wins don't have to be consecutive, thankfully, so a little bit of patience will make completing this challenge less frustrating.

The reward for completing this challenge is a meager $5. You will also get additional Dead Eye EXP.

Win Three Games of Five Finger Fillet

The third Gambler challenge is just as straightforward as the previous two, as you just need to win three games of Five Finger Fillet to complete it.

Five Finger Fillet is yet another of the mini-games available in the Red Dead Redemption 2 story mode. This mini-game is very simple: you need to complete laps by pressing the correct button sequence and do it more quickly than your opponent. Five Finger Fillet can be played, among several locations, at the current Van der Linde gang camp.

Five Finger Fillet, thankfully, is an entirely skill-based mini-game, so learning how to play the game will be enough to complete this challenge. Your opponent will always go first, so use this to your advantage and memorize the button sequence. As the total number of possible button sequences is limited, playing this mini-game a lot will help you commit them to memory, which will make you faster and more accurate.

The reward for completing this challenge is the Gambler Bandolier, which grants a Stamina bonus once all the items in the set have been obtained.

Bust One Poker Player Out in Each Location (Saint Denis, Valentine, Flatneck Station)

Completing this challenge requires a good knowledge of poker and its rules, as you need to bust one player out while playing poker in all the available locations, which are Saint Denis, Valentine and Flatneck Station. Busting out a player in poker while playing at the Van der Linde gang doesn't count toward completion.

Busting out a player in poker means to force another player out of the game by making them lose all money. The only way to do this is to force them to go all in by raising stakes to a high level. Since there's a good chance you will end up failing due to your opponents' hands being better than yours, you will need quite a bit of money. Force at least a player out at the different poker locations to complete the challenge.

The reward for completing this challenge is $10, a very low sum considering how much you can end up spending trying to complete it. You will also get additional Dead Eye experience.

Win Three Rounds of Dominoes Without Drawing Any Tiles Against 2 Or Fewer Opponents

Completing this challenge requires quite a bit of luck, as you need to win three rounds of dominoes without drawing any additional tile.

Dominoes is a rather straightforward mini-game where players must attach dominoes with matching numbers together. The first player who is out of tiles wins the round. In case any of the players cannot attach any domino, they must draw from the graveyard until they get a piece that can be attached.

Winning a round of dominoes without drawing tiles from the graveyard can be difficult, but it's definitely doable. While things are luck-based, there's a way to make things slightly easier: if your opponent is forced to draw from the graveyard, you can get an understanding of which numbers on the pieces he is currently missing, and this is information that can be used to close the round quickly.

As the entry fee is at possible lowest, only $1, you may want to attempt completing this challenge at the Van der Linde gang camp to avoid spending too much money.

The reward for completing this challenge is $10 and additional Dead Eye experience.

Beat the Blackjack Dealer in Two Locations

The sixth Gambler challenge is among the easiest to complete, as you need to beat the Blackjack dealer in two different locations, which are Rhodes and the Van Horn Trading Post. Playing Blackjack at the Van der Linde gang camp does not count toward progression.

Beating the dealer in Blackjack essentially means to win a round of the game. As explained above, you must get as close as possible to 21 with the cards that are dealt to you. The reward for completing this challenge is $15 and some Dead Eye experience.

Beat the Fiver Finger Fillet Player in Every Location

Like the previous challenge, this one is very, very straightforward, as you simply need to beat the Five Finger Fillet players in Strawberry, Valentine and the Van Horn Trading Post. The locations of these players are marked on the map, so you won't have any trouble finding them.

This challenge is more skill-based than most of the other Gambler challenges, as to win in Five Finger Fillet, you just need your fingers to be quick and accurate enough to press the correct buttons at the right time. Make sure you pay attention to the sequence when your opponent is performing his lap and you should have no problem winning.

The reward for completing this challenge is the Gambler Gun Belt, which provides a Stamina boost once the full Gambler equipment set has been obtained.

Win Three Hands of Blackjack With Three Hits or More

Things are back to being luck-based for this challenge, as you need to win three hands of Blackjack with three hits or more.

Hit in Blackjack are the additional cards that are dealt to you after the first one, so winning a hand with three hits and more requires the first card to be of low value. In case you are dealt a card with a high value, just try to play the game regularly to avoid losing too much money trying to complete this challenge. The three hands don't have to be won consecutively, so it's much less frustrating that it could have been otherwise.

You will receive $15 and additional Dead Eye EXP for completing this challenge.

Win Three Games of Dominoes in a Row

The ninth and first to last Gambler challenge is going to require a bit of both skill and luck to complete, as you need to win three games of Dominoes in a row.

Due to the nature of Dominoes, you will need quite a bit of luck in getting the right pieces to win three games in a row. Thankfully, you can make things a bit easier by forcing your opponent to draw from the graveyard by placing the right pieces on the table. To make things slightly less expensive, we suggest you attempt completing this challenge at the Van der Linde gang camp, as the entry fee to play the game is very low, compared to the other locations.

The reward for completing this challenge is $20 and additional Dead Eye experience.

Win Three Hands of Poker in a Row

The tenth and final Gambler challenge is going to be a nightmare to complete for most players, as you need to win three hands of poker in a row.

There's no real way to make things any easier, given the nature of Poker, so head over to any of the locations where the game can be played, including the Van der Linde gang camp and Valentine, arm yourself with a lot of patience and money and hope for the best.

The reward for completing the final Gambler challenge is the Gambler Off-Hand Holster, which gives a Stamina bonus once the full set has been acquired.


Logan Smith

Logan is probably the most knowledgable Red Dead Redemption 2 and Red Dead Online writer we have onboard, having authored the vast majority of all the guides you'll find here at RDR2.org. Having written those hundreds of thousands of words Logan still drops in and makes the odd tweak or update, but is otherwise eagerly awaiting the next massive gameplay updates from Rockstar. Connect with Logan on Twitter.