D&D 5E Advice on revealing a secret identity.

[MaximusArael020]

Hi, all!

I'm trying my hand at a homebrew story for the first time, and I need a little advice.

A character in the party that I control is being kidnapped for actions he took before the party formed. He is being taken to Waterdeep, where he was part of a Thieves' Guild. He had screwed over some members of the guild, fled, changed his name, and is now adventuring with the other players.

Thing is, I would love the head of the thieves' guild to also be a member of the Lords of Waterdeep (5-member ruling council whose identity is hidden by magical helms from everyone and themselves). The party can find the kidnapped character through several means, but they all end up with them being in the guild's hideout, horribly outnumbered. The leader says he'll make them a deal. The kidnapped characters debt will be paid if they can reveal the identity of a specific member of the council (they go by Nicknames in public) and kill them. Of course the players don't have to kill that member, there can be any number of solutions (make a deal with that member, impersonate them, etc). I'm leaving a lot up to them.

However, I'm having trouble conceiving of how they might find out the identity of this particular person. Following them after a public appearance (normally high-importance trials) sure, but there would be safeguards against something so mundane. The party will be level 5-6 by then.

Any suggestions on leaving hints as to their identity? Means to unmask them baring a all-out fight in the chamber? My plan is to have them be the head of one of the other guilds in the city, like the merchant's guild.

Thanks for any advice!

 

[Ed Laprade]

Since he's a DMPC, don't be surprised if the rest of the party decides to throw him under the bus rather than try to mess with one of the tippity top people in the biggest city in the world.

 

[MaximusArael020]

That is totally welcome if they choose that route, however knowing the players as I do makes that unlikely. They were untrusting of him in the beginning, but are growing fond of him. Also, they are very much the "heroic" types, so leaving someone who had fought next to them to die or be tortured would be out of character. But if that's the way they decide to go I won't force anything upon them. I'm trying to be open about how they can accomplish them, I'm just trying to think of some breadcrumbs I could leave for them if they get stumped.

 

[aco175]

I'm reminded of the movies where the one of the masks need to get stolen and then counterfitted and returned before anyone can notice. Then the PCs can follow the magic in the mask and lead to the one wearing it. If they are good then they need a way to save the lord and get back at the thieves. A wrinkle involves one of the thieves knowing the magic and how to follow the magic to the lord and well.

 

[Nevvur]

An informant, maybe? Word spreads in the underworld the guild leader wants to know the council Lord's identity, and someone has offered to divulge the information. However, there's some obstacle preventing that communication, and that's where the PC's debt comes in. The nature of the obstacle is up to you. Maybe the informant is demanding too much money, maybe he wants to meet in a dangerous location, maybe they have to spring him out of jail, etc. Make it a short adventure or a single encounter to get the information from the informant (through payment, persuasion, coercion, intimidation, or violence). When the PCs return with the identity, the guild leader (being an a-hole villain) renegotiates the terms of the debt repayment to include killing the Lord.

 

[ArchfiendBobbie]

An expansion to the idea by @Nevvur below:

Maybe the informant isn't a person. Maybe it's a specially-designed magical tome or similar item that has since gained sentience. But it wants free of its current owner, who is someone the Thieves Guild cannot afford to be caught crossing. The guild doesn't know about it in general, but one member does and if suitably compensated may be willing to part with information on doing the job he cannot.

 

[MarkB]

The thing that immediately occurs to me is that it's probably no more difficult taking on the head of the Waterdeep thieves' guild than taking on any one of the Lords of Waterdeep (especially because unmasking and slaying any one of them is likely to piss off the rest of them). If your players also figure that out, expect them to act accordingly.