The number 1 question that I get asked as a game designer is "how do I win?"
It's also the one question I hate answering.

For one thing, the goal of any game-design is to not have a single winning strategy.
For another, discovering the strategies is a large part of enjoying the game.

So, I don't generally give out strategies. Having said that, Calaboose is wild and wacky enough that
I feel comfortable giving out some pointers to help the serious player get even more serious.

Tip #1: Know the Cards

Bandits and Hucksters are plentiful. There are lots of them - more than any other card in the deck. That's okay, though. They're going to get wiped out pretty quickly. If you look at the card count in the manual, you'll notice that the lower the strength of the card the more common it is. I'm not suggesting you count cards (though a lot of people do), I'm just saying be aware that your next card is much more likely to be a Huckster than it is a Bad Lawman

Tip #2: Keep the Bad Lawmen

Sounds crazy, doesn't it? However, the Bad Lawman is the only card capable of defeating a Gunslinger. In a 5 person game - where you're almost certainly going to go through all the cards - having a Bad Lawman in your hand at the end can mean the difference between winning and losing.

Tip #3: Beware the Gunslinger Showdown!

At the end of the game, it may be tempting to send a Gunslinger after someone with a Gunslinger showing. I've seen games where four Gunslingers head across the table to wipe out a series of hands. This is fun (and weirdly scary), but it can also lead to chaos. If you get a couple players who are way behind, they can try to use Gunslingers to wipe out the other players. To combat this, either hold on to a Bad Lawman (if you can), or lock down quickly once you start to see those Gunslingers on the table.

Strategy #0: The Huckster Gambit

Can you collect all 5 Hucksters? Everyone I know has tried, but no one has succeeded. This is the "all-or-nothing" strategy. If you can pull it off, you probably will get enough points to win the evening, even if you do terribly on the next couple games.

Strategy #1: The Bandit Play

This is the most obvious. Bandit Gangs are worth the most, and the cards are the most plentiful, so grabbing them seems to make sense. Having many Bandits showing puts a bullseye on you when there are more than 2 players, though, so be careful. You're going to want to lock down as quickly as possible - so you'll need lots of high cards (or great table talk) to defend them.

Strategy #2: The Card Shark

My personal favorite. Collecting Card Sharks strikes a great balance between defense and points. Sure, you may not get as many points as the Bandit Play, but you'll avoid being the target and often will sneak out with a win.

Strategy #3: Rustlin'

This is a tough one to win, and is probably only well suited for a game with more than 3 players. Winning with Rustlers means you're managing to prevent others from getting Bandits or Card Sharks, and that's pretty tough. 3 Rustlers are worth the same as 2 Bandits.

Strategy #4: Gunslingers

This isn't so much a strategy as it is sheer intimidation. If you get the cards to fill your jail up with Gunslingers, no one is going to bother you. Hold a couple Hucksters in your hand to defend against Bad Lawmen, and you're all set. Tough to get the cards though.

Strategy #5: Combo

A great strategy. Two Bandits and three Card Sharks is a really good hand (45 points). Three Bandits and two Cattle Rustlers isn't bad either (40 points).

Reality Check!

Whichever strategy you start with, it's probably going to change as the play progresses. Also, this is just one way of looking at the game. For example, one playtester developed a preference for filling a portion of his jail with high-powered (low value) cards early, confident that he could get people to leave him alone in the early game, and draw them into attacking in the late game. This meant that as other people's jails were filling up, his was emptying, and he could send out his high value cards while others were locking up.

That's it - No more tips. Now get back to your Calaboose before someone fills it with Hucksters!