A Gentleman's Challenge

[Doughnut Master]

So, I want to whip up a little side adventure in which two rogues are in a competition to steal an object. They can use whatever methods they like, but they aren't allowed to kill each other.

Any advice on how I might start constructing such an event, or sources to consult? I'd like to try to give them several options, such as conning your way in vs. cat burglaring in from the roof vs. smash and grab, or something like that.

[Silus]

Grimtooth Traps. Lots of them.

[Aidan305]

Are they both players? Or is one an NPC?

In general, you simply want to stat it up as a normal dungeon. Work out traps, NPCs, plot hooks, etc. But try to give it a sense of modularity. Have the actions of one rogue effect what might happen to the other. If one rogue comes to the door looking as if he's ridden for miles with a dire warning for the master of the house have his message (That a master thief is coming to steal the McGuffin) directly impact how things will change as regards the security.

[Cyrion]

How good/creative are the players, and what level of power do their characters have?

We had a similar thing going in a campaign, and the things we had to pilfer or accomplish tended to be odd, and large. At one point we had to acquire an ornamental gargoyle from a cathedral- relatively easy (you'd think...), but not the usual valuable mcguffin. I vaguely remember having to steal a caravan (the whole thing, not just the goods), and as I recall the challenge before the group broke up was to hide a mountain.

Think about making the object not what you expect, but the characters don't know that until partway through. To swipe a bit of wordplay from a Mason Williams song, have the rogues have to steal the Princess' panties. What they don't know is that the Princess refers to her two dobermans as her panties because that's what they do after they've chased people for her amusement...

[Aemoh87]

I agree, it's important for it to be more than just stealing.

First they need to find out about the thing they are stealing, I love the Panties idea because it's funny and even funnier if one manages to steal the panties while the other is thinking about how to nab the dogs. Even better if one sabotages the other to do so.

Two I would make it more about skills, and grimtooth has the best traps in 3.5 period. Anything WotC publishes about traps fails in comparison. Potencially throw in one combat encounter where they have to stealthily knock off guard's without sounding an alarm.

Cap it off with said alarm going off and the rogue having to flee for dear life right after he nabs whatever he is after. Very fun.

[ArcanistSupreme]

You could track each rogue's progress round by round once they get into the manor/castle/fort/dungeon/whatever. Whoever gets there in the fewest rounds gets the item, but that doesn't mean that the other can't swipe it from him/her.

[Sillycomic]

I would suggest not telling them what they have to steal, but rather let them figure it out for themselves.

In the case of the princess' panties, tell them they are required to steal the princess' most prized possession.

It's up to them to gather information to figure out about the princess and talk to different people (just who they do decide to talk to is important, chambermaids versus nobles)

Half of the challenge in this case is finding out what it is they're supposed to steal. (puppies versus underwear... or whatever else the challengers end up assuming is important to the princess)

And have the princess go out of the castle from time to time. Perhaps a rogue would think kidnapping the princess herself is a good way to solve this riddle? Or simply follow her and see where she goes and what she does.

You can stat out the castle as a decent dungeon, but you give them the option to bypass the dungeon completely if they think they can pull something off within the city.

[Doughnut Master]

Cool. Thanks guys. I like the non-traditional angle of the prize.

Anyway, they're only level 5, but they're both pretty creative players. They've certainly handled their fair share of challenges.

[Aemoh87]

I think that at one point in time it would be ideal if they ran into each other... Just to make the situation awkward. I'd also lead them to believe something different than the situation is, like make is appear one has the item already, or have one lead the guards to another. Always fun stuff. But use your DM'ing powers to keep it close, everyone likes a close competition.