Help me Organize a Questline Please!

[Nmomoth]

So I've thought of a questline, one that I think would be pretty interesting, it's just that right now it's mostly just a bundle of loose ideas.

The party that I am DMing is about to reach the capitol of the setting that I placed them in and will discover that its slums are run by a powerful crime ring. An assassin has been hired to eliminate him but seeks the player's assistance in weakening his defenses.

The only details that I've thought of including so far have been a few minor story details like the leader being a tiefling warlock that had originally wanted to help the slums, the city guard is corrupt, and that the gang wants to capture one of the party members and sell her back to her home country (backstory stuff).

All in all I'm stumped when it comes to laying out a quest like this. I've only been a DM for a couple months now and the campaign so far has been mostly random encounters, dungeons, and small sidequests. Any advice, ideas, instructions, etc would be greatly appreciated!

[Puh Laden]

The assassin is hired to eliminate whom? The crime-ring's leader or the city's leader?

Either way, a principle I find helpful is to come up with the motivations of any NPCs first. Think about what they want and what they are willing to do to get what they want. Once that's done, think about what situations the party may come across, or that you want them to come across, within that context and create encounters for those situations (whether social, exploration, or combat). Don't come up with the details of everything at once, but maybe one or two session ahead of time shape your rough ideas into a plan. A bundle of loose ideas is perfectly fine for an urban adventure with more opportunity for social activity than a dungeon. Think through the major possible consequences of the different outcomes of the encounters, including failure. Having that player character kidnapped could be a result of a failure in combat for example. It doesn't have to be though, it could be a result of a solution to another encounter (bargaining for an exchange of prisoners or information).

[INDYSTAR188]

So I've thought of a questline, one that I think would be pretty interesting, it's just that right now it's mostly just a bundle of loose ideas.

The party that I am DMing is about to reach the capitol of the setting that I placed them in and will discover that its slums are run by a powerful crime ring. An assassin has been hired to eliminate him but seeks the player's assistance in weakening his defenses.

The only details that I've thought of including so far have been a few minor story details like the leader being a tiefling warlock that had originally wanted to help the slums, the city guard is corrupt, and that the gang wants to capture one of the party members and sell her back to her home country (backstory stuff).

All in all I'm stumped when it comes to laying out a quest like this. I've only been a DM for a couple months now and the campaign so far has been mostly random encounters, dungeons, and small sidequests. Any advice, ideas, instructions, etc would be greatly appreciated!

I would suggest doing the following:

1) depending on the size of the the criminal organization there might be a leader with several captains (or whatever you want to call them). The boss's job is to oversee the organization and to make political contacts to facilitate things (like those crooked guards you mentioned above), the captains are the ones who run the actual crime. Each of the captains could all specialize in a type of criminal activity; kidnapping, extortion, theft/fencing, gambling and murder lets say). Each of these captains probably wants to be the boss.

2) the tiefling crimelord is from the slums of this city and rose up alongside a friend/brother/cousin who is now a major politician. The tiefling has dirt on the politician and is 'encouraging' him to help out the slums. The politician cannot do this because a) he represents wealthier-types who want the investment in their part of the city and also b) it would work against his business interests.

3) the politician is the one who hired the assassin and the assassin is known to the crime group so cannot infiltrate them herself. Conveniently here come your players! Their job could be to infiltrate the guild and learn about it. They might meet an ambitious captain or two who could help them take out the boss OR they could meet the boss (who it turns out is actually very principled about harming only criminals) who takes them under his wing and is actually interested in helping out the slums. That way they have to make a couple of RP choices:

- expose the crooked politician and guards?
- Help one of the Captains take out the Crime Boss?
- Help the Crime Boss fight off her Captains and force the politician to invest the money in the slums?

[Nmomoth]

I would suggest doing the following:

1) depending on the size of the the criminal organization there might be a leader with several captains (or whatever you want to call them). The boss's job is to oversee the organization and to make political contacts to facilitate things (like those crooked guards you mentioned above), the captains are the ones who run the actual crime. Each of the captains could all specialize in a type of criminal activity; kidnapping, extortion, theft/fencing, gambling and murder lets say). Each of these captains probably wants to be the boss.

2) the tiefling crimelord is from the slums of this city and rose up alongside a friend/brother/cousin who is now a major politician. The tiefling has dirt on the politician and is 'encouraging' him to help out the slums. The politician cannot do this because a) he represents wealthier-types who want the investment in their part of the city and also b) it would work against his business interests.

3) the politician is the one who hired the assassin and the assassin is known to the crime group so cannot infiltrate them herself. Conveniently here come your players! Their job could be to infiltrate the guild and learn about it. They might meet an ambitious captain or two who could help them take out the boss OR they could meet the boss (who it turns out is actually very principled about harming only criminals) who takes them under his wing and is actually interested in helping out the slums. That way they have to make a couple of RP choices:

- expose the crooked politician and guards?
- Help one of the Captains take out the Crime Boss?
- Help the Crime Boss fight off her Captains and force the politician to invest the money in the slums?

I like this idea. A lot. Especially the captains and politician. I'm having fun coming up with each of these characters. Thanks for the help!

[Armok]

If you're setting up the warlock to be the antagonist of this adventure, it may be worth considering who his patron is and the implications this might raise. Since fiends are kind of overdone, allow me to suggest something else entirely. Here's how I'd do this with the fey!

Maybe this tiefling, desperate for the power to change his home, made a bargain with the fey for the power to influence others. He'd have access to many mind influencing spells and abilities this way, allowing him to better work his way to a position of power. (This also sets him up as an antagonist who can be dangerous out of combat, or in non-damage related ways.) For the fey, I'd consider why they'd go into this deal and what they get out of it. Perhaps this tiefling is gathering dirt on highly influential city officials, and he trades those secrets to his patron for power on the sly.

And maybe his patron is ultimately indifferent to his success or failure as long as it's agenda is catered to. You could set up a scenario where the players encounter this patron, whether it be an aspect of it or a messenger pixie, offering a deal. "Oh, you want to know where the tiefling is hiding? As a reward for finding the glade of our communion, I'll tell you... If you tell me something. I hear that the king keeps such splendid secrets..."

And now the players are dealing with whether or not this tiefling deserves to be taken out, and whether or not they should commit the same act he is just to catch him! Or something like that.