Assassinations 101

My new player has begun playing a PC (formerly an NPC) who’s an assassin. His guild is in the nearest large city to where the party has mostly been based: a smallish town with relatively minor problems. The assassin’s name is Gulch, and his background is that his superiors have sent him out into the world to raise funds to upgrade the guild’s headquarters.

This week's game was cancelled, and now I’ve got more time to prepare for the next regular session. I’ve been thinking that it might be great to do a one-shot solo adventure with this player in the interim. Gulch joined the party a bit late after other characters had died, so consequently he’s lagging in experience. I thought it might be nice to line up an assassination job for him to get him up to speed and this might be the right time to do it.

Player spoiler alert!

So I’m relishing the sinister possibilities… One idea I’ve had revolves around two NPCs in town. One merchant was stealing from another. The second merchant hired the party several sessions back to find out who was stealing from him. The group successfully captured the culprits, killing one in the process, both of whom turned out to be the sons of the first merchant. The surviving son is now rotting in a dungeon and the father (who claimed no knowledge of his sons’ activities) has travelled to the big city to hire an assassin to take out his competition once and for all and to avenge his sons.

My loose plan is to have one or two of Gulch’s minor superiors at the guild make a trip into town to check up on him, collect his dues, and assign him the task of killing the friendly merchant who’d previously hired him and his group. I’ve begun to think about the possibilities that the player might decline the job (and be punished by the guild), or that he might feel guilty and fail on purpose, or warn the merchant somehow. If the player takes the job, I have the task of drawing up the target's home, defenses, and daily routine to be prepared for the player beginning the stalking process. It’s all kind of morbidly fun to consider, though I suffer some minor guilt from, in effect, helping to plot the good merchant’s demise.

Because this is Gulch’s first job, and because he’s not yet proven himself, I’m very tempted to have the entire thing be a setup. That is, the two other guild members might have been sent to test Gulch. They may give him some help in plotting the kill, and then when the time comes, they might kill the merchant themselves. One of them might then disguise themselves as the merchant, and taking the proper precautions, pose as him for the planned event. Then if the player chickens out, warns the merchant, or otherwise screws up, he’s busted! All standard operating procedures for first time hits, of course. But will the player consider this?

If the player fails, he might be given a second chance, albeit one requiring even more brutality to succeed. If he succeeds, then I can see an ongoing series of solo games consisting of assassinations when our regular games don’t happen for whatever reason. That might get old quick, or it might not… Though the thief and assassin classes are well suited for solo-play, the thought of running one murder after another might be a little darker game than I’d want to play even semi-regularly.

I’d be interested in hearing about anyone’s fun or enlightening assassination experiences to be able to get some more ideas. From the game only, please.