Moral Gray Areas...

Err... what if they refuse? How do you know that they are going to be working for this crime family? How do you know what they are going to do before they do it? My suggestion when planning that sort of game is to recognize that the game can change at any point from the players working for X to, the players working against X. You need to have some contingency plans to handle this change.

It's no different than in any other campaign, really. If anything, that extra element of the unknown is what makes these kind of underworld games more intriguing than your standard rescue mission. Even if you go "cheap" and threaten their lives if they refuse, there are still ways for the PCs to give the illusion of getting the job done without their bosses knowing the truth. There's just as much risk of players turning down a chance to do a good deed as there is a bad deed... it's just not as considered as one might think.

Players - good players, mind you - will go along with certain elements so long as they know it's part of the story and they don't feel forced into it. Hell, sometimes they'll go with it even when they are forced if they trust you. I've had players keep secrets from each other for years at a time and they were always welcome to spill their guts anytime they wanted but because they were involved in the secret, they were willing to keep it up. And the players left in the dark were pleasantly surprised when they found out another player was in on the action. It takes the onus of the surprise away from the GM (because players NEVER trust a GM) and brings the players into the action. Allow everything to happen organically and you'd be surprised how it works out.

The trick is knowing your players. If you don't think your players will go for it, don't risk it.
 

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I think there's 2 different scenarios.

Is this the setup for a new campaign?

Or is it an existing campaign, about to move into Mob territory?

If its the former, you should probably tell the PCs that you plan on running a "working for the Mob" campaign, and that they need to make PCs that can work in that framework. That, then lets them figure out, discuss and create something within that limitation. Thus, you don't have to ban the paladin, the players rule him out as impractical, unless one of them has an idea on how to make it work (undercover).

If it is the latter, then you already have PCs, you're not ruling out paladins, the players are the ones deciding to work in an environment where they won't be meeting any paladins to join the party.
 

This is how things should go for the smoothest game possible.

DM: Hey guys, I've got this neat concept for a game where you guys are working for a mob boss.
Players: Sounds neat.
DM: Of course this closes off some character concepts. You'll all be people working for a mob boss not heroes rushing off to slay dragons.
*players nod*
DM: Oh, I also thought that it might be interesting if one of you was a mole trying to bring the mob boss down, obviously that could lead to a lot of party conflict so I was wondering what you guys thought.
Players: [Insert yes or no answer here]
DM: Alright then, let's work out what characters people want to play, how they ended up working for the mob boss, and how they all know each other.
 

Even the most lawful good character can be fitted into a mob-boss story with the right backstory. Characters who act under the orders of the bad guy despite being good litter literature.

- Failure to obey will cause harm to innocents or loved ones
- At least this way, I can do the job in the least harmful way
- I gave my word
- I believe that despite the means, the final goal is a good one (mob bosses after all profit most when a city is profitable and functions in a generally lawful way)
- I'm taking him down from the inside
- Someone I respect told me one of the above ("Well, I don't see how helping this guy will further the greater good, but if you say so..."
- Someone I care for is working for the organisation and to redeem them I need to be near them.

etc etc.

But in all cases you need to work together with players to create a credible backstory.
 

Old soapbox of mine -- A DM should define good and evil in their games, this creates your cultural taboos and conflicts. It also takes those moral grey areas and makes the players look beyond good and evil to things like loyality, interigity, friendship, etc.

As an example:
You are building a "crime family culture", what is good to this culture. Loyality, honor & intergity to family, wits, expanding the business, etc. What is seen as evil; not being loyal to family, not having intergity with family, being dumb, failure at business. What this does now; creates a family first culture, fathers & mothers are the leaders, honor to family is measurable (you can make up rules for it).

Now, why is it a crime family? In many games worlds there are a number of laws; state, city, guild, church, country. Crime is normally in conflict with one of these, you just have to decide which one. In this case, say city and that the "crime families" have issues with taxes and an outside government now ruling the city.​

As you can see, this sort of builds itself.

As far as paladins go, they have a code, look at the Boy Scout code and you will find that it allows a lot of flexiblity.
 

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