How would a criminal organization put "candidates" to the test?

[Citan]

Hi all!

I'm coming to you for help because I realize I'm out of ideas.
Long story short, my players want to get hired into a criminal organization (or, at least, get information without being considered a threat) to try and expose their dirty secrets.

I was thinking about just making them fulfill a few strengths/dex tests, have some interrogation to check their backgrounds, then put them on a mission.

But I just thought, "which kind of missions"?
I mean, obviously a reasonable syndicate would not put newcomers to any task that may reveal some secrets.
So, no "carryman" transporting merchandise through secrets passages evidently.
Even a "protection" mission seems awkward to me, because if any marchandise/people is really worth to the syndicate, it would rather ask people that are already known and trustworthy, no?
And I don't see how some mission like "go ransom random people" could get them on a lead...

So, my question: what task could I give to my players that would be "logical", interesting enough, and still gives them some opening to go and find some leverage against the syndicate?

In case it helps, the syndicate is one of the big three in the city: it deals in weapons and drugs, especially some kind of healing plants and berries, and has ties with local police and government.
The city itself is along the coast, so the main way of trade is through the port. Although the syndicate also created over the years a few tunnels that connect their main hideouts (taverns) up to the nearest forest.

Thanks for reading and for any help you could provide.

[War_lord]

Send them to do something simple, like rough up local merchants for protection money, or deal with a freelancer who refuses to join the organization. Simple low risk stuff that proves that initiates can handle themselves and are willing to commit crimes.

[tieren]

I ran into this when my party wanted to join a gang controlling a town.

I had them prove themselves by doing some grunt work for the gang, basically shaking down some local businesses for protection money. They then had to make the choice if the ruse of joining the gang would go so far as to hurt innocents, or if they would just pretend and pay the protection money themselves or what not.

[Specter]

How evil is the organization? If it's a ruthless chaotic evil psycho organization like the White Masks in my campaign, they could make the new members torture or kill some of their enemies (or innocents). If they're evil tending towards neutrality, they could have the characters retrieve an item from a dangerous place, or distract the guard while the members make a move somewhere.

I personally would turn this into a dilemma: should we kill this innocent man for information or let him live and go back to square one? Should we shake down their enemies or try to make an alliance with them? Etc.

[JobsforFun]

How evil is the organization? If it's a ruthless chaotic evil psycho organization like the White Masks in my campaign, they could make the new members torture or kill some of their enemies (or innocents). If they're evil tending towards neutrality, they could have the characters retrieve an item from a dangerous place, or distract the guard while the members make a move somewhere.

I personally would turn this into a dilemma: should we kill this innocent man for information or let him live and go back to square one? Should we shake down their enemies or try to make an alliance with them? Etc.

A good question of morals is always fun when it comes to things like this, of course if everyone in the party is around the same alignment like LN they'd probably all agree on what to do. I would personally either do the the moral dilema or some sort of mission the gang sends them on that is a suicide mission since so many of their members have died doing it, just to see if they group can pull it off.

[BW022]

This assumes that the group is hiring... :smallsmile:

Lots of ideas...

1. Acts a middle-men for a transaction. Maybe with someone who doesn't like the group.

2. Get something from another group, the guard, some noble, a church, etc. i.e. someone who doesn't know the PCs are helping the group.

3. Long-term service in some minor roles -- guard duty, renting a building, selling stolen goods, etc. Nothing major.

4. Kill someone -- a guard, minor noble, another gang leader, etc.

5. A "setup" mission. Rob a noble, murder a guard, etc. However, the noble/guard, etc. is a member of the gang and can report if the PCs don't try to carry out the mission. If they do, the person who gave them the mission is nearby to stop them.

6. Distractions. Make a simple distraction to keep the guards at a warehouse busy. Report a fake crime to get the watch to send folks somewhere else.

etc.

[DivisibleByZero]

There would most assuredly be some type of loyalty test. Possibly to see if they could follow orders when they don't want to, or something to that effect, but there would absolutely be something along these lines.

[Addaran]

H
Even a "protection" mission seems awkward to me, because if any marchandise/people is really worth to the syndicate, it would rather ask people that are already known and trustworthy, no?


Could work with a protection mission for an independent. Someone who payed protection money to the guild but isn't linked to their actual business. If it's something distasteful with consequences, it could help the syndicate judge the candidates' morale. Help protect a necromancer while he's grave robbing to get new minions? Maybe even go so far as make it happen during a guard's shift, so they have to kill him to succeed the mission. A spy would observe to see how the players react. Either they help someone evil and innocents will probably be hurt, but they get deeper in the organization or they save lives now but lose their opportunity.

Or Specter/BW022's idea of distraction missions. Have them learn the consequences they helped achieve. A local priest of a good religion assassinated or a family giving up their house and become homeless because they were beaten. If they continue to help do distractions, the syndicate will trust them eventually, but they'll have helped lots of crime.


Maybe a protection mission for someone they want to get rid of. The syndicate pretend it's one of the higher up and set it like it's a big important mission. There's fake proof linking to other "criminals". If they act on it, turns out they helped get rid of a liability (who though he was on his big mission to gain rank) and they accuse lots of other innocent people. If they do the work well, they can always get rid of the liability another way (maybe have the players kill him) and the syndicate have "proof" that the players are on their side.

[BurgerBeast]

You really have to put yourself inside the heads of the higher-ups in the organization. Why would any organization want new recruits, and why would they want them to advance?

I would think that the trials would progress through some "levels."

1. The first test would be whether they can get jobs done without any babysitting required. If you are asked to do a job, can you do it without making it my problem? Basically, are you competent?

2. How much responsibility can you handle? If I need someone to start-up an organized crime operation in a neighbouring town, I'm going to pick the best candidate. How do you stack up, in terms of skill-set and general problem solving?

3. Can you be trusted? How much would it take to crack you? Again, if you're going to penetrate the inner circle at the top of the organization, it comes down to the most trustworthy candidate.

You could get a lot of mileage out of playing all of this out if you wanted. You could create the boss or sub-boss and his motivations and a list of things that impress him and things that irk him. You could try to drop hints to the players about these to reward clever play. You could progress though trials that push each of these to further extremes to see how the characters do, and as mentioned above you could "up the ante" by raising the ethical stakes to increase dramatic tension. Of course you could hand wave much of it too, if you wanted to move in a different direction.

[Hrugner]

The criminal organization would hire people to do their perfectly legal work doing it all above board with occasional cash bonuses given below the table. After a few such jobs the criminal organization would have them do a less than legal job without letting them know that it was illegal. After some time has passed, the new recruit would be tested either incidentally or deliberately. If they are caught doing the illegal activity of which they were unaware, and they don't rat out their criminal organization, then after they've served their time they'd be welcomed back by the organization. If they never get caught then the criminal organization would send them on a job or to a place that they knew would turn bad forcing the recruit to either step up and defend his allies or flee. Meanwhile, all the untaxed income is tracked in the criminal organization's ledgers ensuring that anyone who turned on them would also be exposing their own crime.

The easiest way to do this in game is to have the players seek employment with a front organization like a warehouse or sea port. After they've worked there for awhile, they get a job to wait outside some other building to help load or unload some goods, they are told it's in a bad part of town and may want to arm themselves to send a message. Meanwhile, inside the building, some long time members of the organization are robbing the place and are forced to flee right into the waiting party who need to chose to either kill the pursuing authorities and join the criminal group, or abandon the ruse.

[KorvinStarmast]

If you want something realistic, do a little research on American street gangs who have some fairly interesting, though brutal, initiation rites.

A couple of decades ago the "beat in" method was popular among a few San Diego gangs (California, USA).
Successful burglary.
Successful hit ( a few of the hard core drug gangs a friend of mine has been working against for over a decade).

How much versimilitude are you after?

[Sabeta]

I played a game recently where you work for a criminal group. Technically, they're more on the Chaotic Good side, fighting the system and the goverment for the sake of the people, but it's not hard to just pluck the moral victory out of the reward to give your characters that mean feeling.

Anyway, the players are given three seemingly unrelated quests.
1) Find a Scholar
2) Ambush an Ambush
3) Burn down a Warehouse

You learn, that all of these things are connected. The Scholar is found in a mining camp gathering an extremely toxic ore under heavy guard. Apparently, this ore when diluted loses much of its toxicity, and actually becomes a healing tonic, but with the caveat that it's extremely addictive and has many nasty side effects.

Then, you head to the warehouse, where you find it stocked the brim with crates full of Elixir with the Church's seal slapped on it. You of course burn it down as requested.

Then, you hit up the Ambush site. Turns out these guys are slavers who caught that Scholar from before, and wouldn't you know it they've also got crates of Elixir in their camp with the Church's seal slapped to the side just like the warehouse.

The "test" was less about a criminal syndicate finding some goons to do their dirty work, and everything to do with finding people who could use the clues they were given to make informed strategic decisions. Had the PCs not made the connection their contracts would have been terminated and the PCs likely would have been silenced in the very near future. That connection being that the Church was distributing highly addictive chemicals to the people in order to help control the masses, and when their next assignment was to assassinate the pope in his own home the PCs didn't need to ask any silly questions about why he deserved it. They all knew what he'd done, and while they personally didn't care they were doing it for a greater good (this is an evil party after all), they did see it as an opportunity to strike a decisive blow to the church which would force some of the big players that the PCs wanted to kill out of hiding. They even managed to trick a Paladin into joining their team.

TLDR: Give them quests that are kind of easy, possibly even harmless, but are all connected by a one or more common elements. You can't really rely on them to figure out that putting the puzzle pieces together on their own is necessary, so make sure the Organization prompts them for their thoughts on their missions, before revealing the "real" final test of doing some kind of crazy heist or assassination now knowing why they need to do it. These are all quests that have at least one degree of separation from the Organization so there's no risk if they botch it, but still connect to their true goal so that the players can figure out what they're getting into.

[Saeviomage]

I imagine that a criminal gang want to
1. satisfy themselves that you are willing to do what they want
2. get dirt on you so that you can't go to the authorities
3. satisfy themselves you are competent
4. not tell you anything you could use against them

Given that, I imagine the first several jobs will be closely monitored wetwork that requires little or no finesse, no secondary motives and most likely with targets given through an intermediary.

They'll probably also be informed upon, but in such a way that if they keep mum, they'll get off.

[Citan]

Thank you all very much for your ideas and comments. :)
Had no time to answer yesterday night since I was DMing, just had the time to look over part of the answers before starting. ^^

I finally went with some "middle-ground": asking them to retrieve some precious object that was currently in the possession of another gang, while avoiding any kill, not especially because of high morals, but just to avoid rising any unwanted sparks between the two groups.
That way, it was in "acceptable morals" for them, and was imo a worthy test of their skills (along with a chance to see how they behaved).

The place was a mansion with ground and 2nd floor on the outskirts of the city, supposedly guarded by 5 people.

Well...
It went fairly well at first, the Monk/Cleric Halfling using Thaumaturgy to try and distract some guards of the ground floor by opening/shutting windows/doors as if one guard was pulling a sad, uninteresting joke on others.
All the while human Ranger used Acrobatics to reach the 2nd floor and entering from a window. Alas, she didn't succeed in being quiet and made some noise. The guard moving around upstairs started coming to see, so she went to the next room by inbetween doors, then because nowhere to hide, rushed into the last room and found herself facing a guard that was ordered to always stay in the room to watch the "safe".
Instead of trying any way to silence him without harm, she just put an arrow right in the head (critical XD) before he could even react.*

I really feel some mechanics of D&D awkwards, especially the Stealth and surprise ones. Also the fact that someone grappling another may still miss his attacks. I explained to my players that when he missed nevertheless (even when I gave him advantage because he put the grappled enemy against a corner wall, so I considered him restrained), it was because attacking while grappling is still not natural, plus the other one still had legs/arms available, so he couldn't expect auto-hit.
Still, I felt him pretty frustrated at a time.
Same when he missed an arrow shot from a 3 meters distance on an unsuspecting guard. I explained it as him being somewhat unsettled because of his fights second ago with the other guards, thus not having his usual focus... But he was a bit infuriated. ^^

Then the other guard came, she tried to muffle him while killing him, but ultimately failed, so he cried for help, alerting the others. This ended in them killing all guards fairly easily (they had some luck, I had none ^^), then took their time eating guard's meal, pulling them all inside the house and sitting them with many alcohol around, before retrieving the treasure then putting the whole house on fire to make it look like an accident.

Now... Sure, this was a good idea "after the fact". But, beyond the plain fact they DID KILL EVERYONE in the end so that will be known whatever happens...
Wouldn't it be natural that the Guild sent someone to spy on them to see how they managed, and will report the whole thing in details?

That was my gut intention, but I wouldn't want to give the impression that I just punish my players for not strictly following orders. Still, I see no way to give them the proper reward, and not sure about how the Guild would react to a half-assed job (on one hand, this makes 5 enemies less, on the other, the other gang will have serious doubts about this because the retrieved treasure was something they competed over since a long time)...

Anwyays, thanks again for all the advice, hope that helps others too. :)

[Addaran]

Given them only 50% of the reward and a scolding for not following the orders. (even without a spy, the whole place burned down, it's probably not a coincidence).

Then more testing missions before the Guild really trust them!

[Citan]

Given them only 50% of the reward and a scolding for not following the orders. (even without a spy, the whole place burned down, it's probably not a coincidence).

Then more testing missions before the Guild really trust them!
Yeah, I'll probably do that, a "guard" mission with another guy so they have some "nanny" watching over them and avoid further massacre (well, theorically... My players did not clearly tell their character's alignment, but they really tend towards Chaotic Evil, both of them XD)...

[Camman1984]

I sent my players on a carry man mission, to deliver a 'highly valuable' package which was actually just a fake ring with a minor spell to make it easier to scary on. the party never opened it and went to great lengths to deliver the package.

[Typhon]

For a first run mission, send them on a protection/retrieval mission. Either they are retrieving some mcguffin from a house of ill-repute deep in another gang's part of town or they need you to escort their kid to school. School being an academy for training monks and the kid is a teenage A*****E. The mcguffin could be some jewelry, that they realize after it is brought back looks gaudy.

Point is they are getting their foot in the door. Gangsters will likely test how much they want to be part of their fine association. Plus, good reliable help is hard to come by.

[Hrugner]

Now... Sure, this was a good idea "after the fact". But, beyond the plain fact they DID KILL EVERYONE in the end so that will be known whatever happens...
Wouldn't it be natural that the Guild sent someone to spy on them to see how they managed, and will report the whole thing in details?

I'd have the spying come in the form of an accusation from the competing gang. Their boss ensures that the players are there to hear the accusation, and get to see their boss deny having any involvement in the fire. Then after sending the rival gang person on their way, the boss can grill the PCs and tell them what they need to do to make things right.

[BurgerBeast]

I might be unique in how I go about handling experience, but I would give the PCs full experience. This is balanced by the fact that the way I would handle the story-consequences is perhaps more severe than how others would handle it.

To my mind, these PCs have clearly failed to do what they were asked to do, and the criminal organization is not the type to go for second chances. Once you screw up, you're no longer a candidate for the work. However, their immediate higher-up would almost certainly recognize that this is a group of "thugs" with some obvious utility. Only an idiot would ever ask them to take on any delicate espionage from this point forward, but if a nuke is needed? These are your guys.

I would expect any savy criminals within the organization to deny any criminal association with these "thugs," but to keep them close at hand as "contractors" for any dirty work or message-sending violence... these PCs have defined themselves as chainsaws rather than scalpels. I would say that if they want to be known as scalpels, they'll need to try somewhere else where their reputation does not precede them.

[Saeviomage]

That was my gut intention, but I wouldn't want to give the impression that I just punish my players for not strictly following orders. Still, I see no way to give them the proper reward, and not sure about how the Guild would react to a half-assed job.


1. You don't give a job like this to someone new if you're actually keen on zero fatalities and discretion. Like I said before, you give newbies jobs you don't actually give a crap about.
2. Their reward will be more jobs that are blunt and deadly and low paying. Finesse is expensive and the practitioners valuable, brute-work is cheap and the practitioners disposable.
3. I recommend their employers inform on them. Not enough to actually give the guard a case: just a general "point them in the right direction". It's a test of loyalty and smarts: if the PCs do something dumb, they fail. All they have to do is keep mum about the job and the guard have nothing.

[Dragolord]

Have them assassinate members of a "rival gang", who later turn out to be fellow applicants ordered to kill the party. The sort of jobs the survivors get will then be tailored to their approach.

[RumoCrytuf]

Send them to do something simple, like rough up local merchants for protection money, or deal with a freelancer who refuses to join the organization. Simple low risk stuff that proves that initiates can handle themselves and are willing to commit crimes.

Are we in Skyrim? Tell Brynjolf I said Hello :P

[MadBear]

I'm a bit late to the party I know, but I thought I'd answer this anyway.

To me, a criminal organization wouldn't hire someone without having leverage over that person. Whatever the mission was, they'd want to use it as "dirt" on the adventurers that they could later use to discredit them, or harm them in some way.

Maybe have them rob a local merchant in town, (but unbeknownst to the players this guy is also part of the mob).

Then later, if the players try and turn on the mob, they can plant the stolen goods on the PC's and give evidence to the merchant to discredit anything the PC's try and say.

A more brutal/morally grey area might be to have them murder someone, and provide the mob with the murder weapon. that way, if they ever betrayed the mob, they could go to the authorities and reveal that the PC's committed the murder.

[Citan]

Hi everyone!

Sorry to have kept silent for so long (I could not even say "I did not have time to answer because of work" -although I do work alot these days- considering the number of lenghty posts I made recently XD).

Just wanted to thank you all for your feedback (also constructive criticism about how I managed this in the first place). I have a much clearer way of how to handle the "aftermission rewards" and everything that follows.

When (if?) my next session has happened, I'll post a quick conclusive feedback.
Unless it would end as thread necromancy (we had to postpone and now next session won't happen until some weeks sadly :/).

Cheers!