Head of the Thieves' Guild

[Trit One-Ear]

My players are bound in the next session or two to cross paths with their local thieves' guild. So far I've painted their leader as a good-spirited half-elf, known for loving card and dice games. He also is not very cut-throat when dealing with thieves outside the guild.

What's more interesting to you as a player:

-A guild leader who appears jovial and good-natured to the public but does his messier dealings all very below table...

or

-A guild leader who actually is a good-natured leader, but who's right hand man is displeased with the less brutal approach the leader is taking with the guild?

Trit

 

[Dr_Ruminahui]

How long do you want this crime boss to stick around?

Because, at least from an "realism" angle, a crime boss that is soft on the competition, especially that not recieving the protection of another crime racket, is not going to last long before he is either picked off by competitors, or (as you have alluded) by a subordinate.

I mean, in the world of organized crime, for a boss being seen as weak is a death sentence.

 

[MortalPlague]

I find the second one much harder to believe.

I really enjoy that first one, however. The man who smiles, donates to charity, takes in orphans, oversees the soup kitchen, and hands out bread to beggars has a squeaky clean public image. He's unassailable. Unless somehow the murders he orders can be traced back to him.

 

[SensoryThought]

I like both.

Having the CG leader being lazy/easygoing/popular might make the guild very good for recruiting - thieves don't like rules. He could also have an ace in the hole (magic sword, ring that teleports him out of danger etc) that means his brutal second (LE) who wants to restructure can't assail him. But he might want to recruit some hapless pcs to steal that ace.

 

[Radiating Gnome]

Trit, if you have the time to check it out, you need to watch the second season of Justified. Mags, the matriarch of a backwoods hillbilly clan, is an amazing portrait of the sort of guild boos you're looking for (in your first idea, anyway)-- motherly, down-home, but absolutely ruthless.

 

[Quickleaf]

AD&D Den of Thieves has some great stuff for fleshing out a thieves' guild, worth checking out.

Your half-elf boss sounds like an unscrupulous casino/tavern owner, so I think you could work another angle and make him super local, so that the next town/city down the road have heard of him and respect him on his turf, but that more serious thieves guilds don't take him seriously. He has his niche, sort of like Rick in Casablanca, but he doesn't have far-reaching influence or an army of assassins to do his bidding. In fact I could see his "thieves guild" as being no more than 20 thieves who daylight as workers at his casino/tavern. With this setup he is more of a networker and fixer, with some funny business on the side.

If that concept doesn't work for you, then sticking with the debonair but secretly dangerous boss sounds more believable.

 

[Ryujin]

The first is the type of boss I would prefer. A truly 'soft' gang boss doesn't last long. One who is a good politician, putting a bright face on everything he does out in the open, but brutal in the 'back room', is much more believable.

Think of the stereotypical Mafia Don. He's a good, loving family man who might even support charities, build parks, and feed the poor. He has a complete separate life, away from his family, in which he has whole families killed for crossing him. People just 'disappear' into the river, building foundations, wood chippers......

Stay on his good side and you might never see the bad. Unless he hires you to do that work for him, of course.

 

[LostSoul]

A little from column A...

A guild leader who appears jovial and good-natured to the public but does his messier dealings all very below table... + who's right hand is a good-natured leader, but is displeased with the brutal approach the leader is taking with the guild.

 

[Trit One-Ear]

You guys are mostly right... I can't see him surviving long in the city I've put him in unless he's willing to cut a few throats. His softer-side characteristics started as a little slip on my part when the players asked "Why isn't he angry about so and so stealing this item outside of the guild?" I think I can reconcile this though.

Finasaer Gellantara is the half-elf head of the thieves guild. A genial person, he spends most of his days playing cards and dice in the Lucky Witch, a local gambling hut. He generally keeps his hands clean, and the populace of the city respect him as one a gentleman of the underworld. Even other thieves pay him cuts more out of respect than anything else. The Duke's Master of Secrets also has very little dirt on him.

What the heroes (may) eventually discover is Finasaer's calm, merry demeanor conceals a fiery temper that, once awakened, is vicious. Finasaer's crimes are all done in secret, and rarely these days, but his ability to seek out and destroy those who wrong him is murmured about in only the deepest gutters. Mostly dismissed as rumors, not even those closest to Finasaer believe he is capable of some of the horrors whispered about. Perhaps there is something magical to Finasaer's ability to remain innocent while committing his darker crimes...

Trit

 

[Ryujin]

You guys are mostly right... I can't see him surviving long in the city I've put him in unless he's willing to cut a few throats. His softer-side characteristics started as a little slip on my part when the players asked "Why isn't he angry about so and so stealing this item outside of the guild?" I think I can reconcile this though.

Finasaer Gellantara is the half-elf head of the thieves guild. A genial person, he spends most of his days playing cards and dice in the Lucky Witch, a local gambling hut. He generally keeps his hands clean, and the populace of the city respect him as one a gentleman of the underworld. Even other thieves pay him cuts more out of respect than anything else. The Duke's Master of Secrets also has very little dirt on him.

What the heroes (may) eventually discover is Finasaer's calm, merry demeanor conceals a fiery temper that, once awakened, is vicious. Finasaer's crimes are all done in secret, and rarely these days, but his ability to seek out and destroy those who wrong him is murmured about in only the deepest gutters. Mostly dismissed as rumors, not even those closest to Finasaer believe he is capable of some of the horrors whispered about. Perhaps there is something magical to Finasaer's ability to remain innocent while committing his darker crimes...

Trit

If Finasaer was a sociopath, he could smile his way through the most bloodthirsty order