Character Name: Chuck Wengam
Inspired by: No known inspiration
Life Points: 4
Ability Type: Offensive (since the activation of the ability involves losing a life point, it is hard to classify this character as defensive, or even neutral)
Ability: During his turn, he may choose to lose 1 life point to draw 2 cards
Activation: Chuck Wengam's turn, whenever he has more than 1 life point, he may deplete his health until his last life point. As the Dodge City rules explain, "He may also use this ability more than once in the same turn; however, he cannot choose to lose his last life point this way."
Cards enhanced by Chuck Wengam's ability: Beer, Whisky, Tequila, Saloon, Canteen, Volcanic, General Store
Cards more powerful when played against Chuck Wengam: Jail
Ideal roles: Deputy, Outlaw
Good role: Renegade
2-player value: Inconsistent. If Chuck Wengam has full health, he can deplete his life points to finish off his opponent, especially if the opponent has low health. However, if Chuck Wengam has low health, his ability will not serve him much good. Since Beer no longer has any effect, he will have to pray that he gets a Whisky! Tequila, since it takes two cards to play, is only somewhat useful. Chuck Wengam will get rid of cards that are of no use to him and hopefully get better ones, but then he is only breaking even. Saloon gives Chuck Wengam's opponent life points, so that is of questionable value at this time in the game. Chances are Chuck Wengam's opponent will finish him off unless he prepared for this 2-player duel by having many cards in play in front of him.
General Strategy as Chuck Wengam: Since Chuck Wengam must lose life points to gain cards, it is to his best advantage to hunt for Beer cards, and those also of the alchoholic beverage family (Saloon, Tequila, Whisky) and Canteen (who knows if it is filled with alcohol o water? I liked to imagine that it is more Beer). That way each time Chuck Wengam uses his ability, he can replenish the life point cost. If he draws an alcoholic beverage card (besides Canteen) by using his ability, he can use his ability again, and replenish his life once more. Drawing these cards allows him to channel his ability. General Store is a beloved card for Chuck Wengam, especially at the beginning of a game with many players, because there is always a high chance of that card for producing an alcoholic beverage or two for him to draw from.
At the beginning of the game, I would wait a little while before trying to use Chuck Wengam's ability offensively. Only in the 5 (or less) player games can it be advantageous for him in any role to start being aggressive right off the bat. Usually, an Outlaw needs to make sure his other teammate can help him against the Sheriff. So use Chuck Wengam's ability initially to gain blue and green cards to play in front of him. Try to build distance between him and his opponents, and gain offensive cards that will help Chuck Wengam against any potential enemy. While Chuck Wengam might store up alcoholic beverage cards for an offensive thrust, I wouldn't store up more than one. Other players know how powerful those cards are for Chuck Wengam, and might easily steal or discard one of them from his hand. Unlike Tequila Joe, Chuck Wengam doesn't really need to store up these cards to get benefit from them, so most of the time I would use them as quickly as possible.
Chuck Wengam's ability also allows him to gather cards together that give nasty combos (Indians!, Duel, Gatling/Howitzer, BANG!, Buffalo Rifle, etc.) when able to be played against an opponent in one turn. Of most use, of course, is the wonderful Volcanic. If Chuck Wengam can get his hands on to one of those, and he has full health, he is almost guaranteed to be able to knock out the opponent to his left or right (given that they are within reachable distance). He shouldn't play the Volcanic out of his hand until he is ready to use it. Naturally, BANG! isn't about knocking out one player typically (unless it is the Sheriff), so most of the time Chuck Wengam can't afford to unload a Volcanic until he has only 1 life point left against his opponent. However, if his Outlaw teammate is ready and has a good card set, Chuck Wengam might just do this and win. I would recommend playing more carefully, so that Chuck Wengam always has more health available in case things don't work out as easily as it might seem. Unloading on an Outlaw is great if Chuck Wengam is a Deputy (his best role, in my opinion), since you get that wonderful 3 card bonus if you off the Outlaw. After you off one opponent, I would recommend playing it safe again, if possible, and trying to regain health and other defensive cards. That is, unless you didn't diminish any life points in killing that player. Then precede to use your ability in conjunction with strong offensive cards once more. This "unloading and turtling" technique is much that for Vulture Sam.
Playing against Chuck Wengam: As with other characters whose abilities are activated during their turns, Jail is a good way to silence their ability. Chuck Wengam also has to lose life points to use his ability, so Jail will be more effective against him when he has many life points. He is hardly dangerous when he has 2 or less. Be very careful when playing General Stores when Chuck Wengam is in play. Unless he is last in line, or second to last, or there are very few players in the game, you may be giving Chuck Wengam a free alcoholic beverage card. Hopefully, the others in line will see the wisdom of not letting Chuck Wengam get his hand on this card if you are not looking for an alcoholic beverage yourself.
If Chuck Wengam has not been using his ability, but just playing it safe, there is a good chance that he is storing up an alcoholic beverage card in his hand. I would recommend trying to steal or panic a card from his hand in this case. If Chuck Wengam plays a Canteen, try to remove it from him before his next turn so that he will not able to use it. If he has a lot of health and has played a Volcanic, try to get that gun away from him as soon as possible, as he will start unloading on an adjacent opponent very soon (if not right after he plays it).
But all of this so far is tangential to the main strategy against Chuck Wengam. As with Vulture Sam, Chuck Wengam should be one of the first players you try to eliminate. Since Chuck Wengam's ability involves losing his life points, you can keep your thumb on him by keeping his life points low. He has a lot of early game power (with the high amount of life points, and other players to serve as buffers and potential card bonuses), so I would try to gang up on Chuck Wengam early on. Use offensive cards in conjunction to pummel him, and then it should be very difficult for him to use his ability in an offensive way.