A Cumbersome Blackmail System

How to set up a blackmail opportunity (but in a cumbersome way that I no longer like).

First, you need a scandal: http://detectmagic.blogspot.com/2014/02/scandal.html.

Then you need a

Target

The target of your blackmail is the moneybags. The target may not have committed the blackmailable offense himself, but he is in a position to pay to keep things quiet.

To get a target:

• make something up, or:
• use an NPC generator, then:
• determine social position of target
1. roll (low/med/high): 1d20 (9- low / 10+ med / 18+ high)
2. interpret roll
1. high: target is tier 3
2. med: target is tier 2
3. low: target is tier 1
3. interpret social tier
1. tier 1 
1. smart merchant
2. decorated officer
3. influential priest
4. aristocrat
5. lower council member
6. enterprising alchemist
2. tier 2
1. connected merchant
2. blood very old and blue
3. upper council
4. religious magisterium
5. accomplished wizard
6. military council
3. tier 3
1. dynastic family
2. close council
3. high priest
4. monopolist
5. general
6. archmage

Subject of Scandal (50% chance target, else target's . . .)

1. spouse
2. lover
3. sibling
4. aunt/uncle
5. father/mother
6. grandfather/mother
7. political / business / religious ally
8. child
9. subordinate
10. superior

Always name everyone. Have lists or generators handy.

Base Payment

The base payment is the maximum the person is willing/able to pay to prevent the revelation of the worst kind of scandal.

You can do this according to what seems legit to you; or, if you're using 4e like I am and if your economy works the way mine does:

• choose social level within tier, or:
• roll 1d10 to determine social level within social tier
• user level to determine base payment
• a standard threshold = XP in gp of a standard creature of target's level
• further specify base payment according to identity of subject:
• target: as solo
• person target cares most about: as elite
• target's family: standard
• other relation: minion

Payment Modifiers

Some factors can alter how much a target is willing to pay, or if they're willing to pay at all (take highest payout):

• If the scandal involves a capital crime or the target stands to lose everything, the base payment stands
• If the target is responsible for loved ones who will suffer from the scandal, the base payment is halved
• If the target will suffer consequences from which he expects to rebound:
• If the target is respectable, base payment is halved
• If the target is shameless, base payment 1/10
• If the target expects no real consequences, payment refused 

Proof

Okay, but what proof do you have?

1. testimony of unreliable/compromised witness
2. testimony of single reliable witness
3. testimony of multiple witnesses
4. knowledge of something otherwise unknowable
5. magical surveillance tapes
6. personal effects of subject
7. damning correspondence / records
8. rumor
9. personal sign/sigil of subject in compromised context (e.g., brand on illicit goods)
10. signs in the body /possessions of the subject 

Note that, depending on your setting, the value of testimony may be altered via magical means of lie detection, penmanship, ownership, divination, etc. 

And how did you come to find this proof?

1 witnessed act/signs/evidence yourself

2 overheard subject / witness discussing / confessing / bragging

3 found correspondence/records just lying around

4 found evidence while pickpocketing/heisting

5 witness came forward with info expecting reward or as payment for debt

6 intercepted correspondence / shipment

Confronting the Target

To blackmail the target, you've got to blackmail the target. How? This is up to the players, but here are some ideas: 

1. write a letter requesting a meeting
2. attend a social function where he is certain to appear
3. hang out at his favorite club
4. knock on his door

Making the Proposal

When the party actually proposes the scheme (including the desired payout) to the target:

• if target is honorable and is overcome with guilt, he can't be blackmailed; he reveals it himself within the week, no matter the consequences
• if the target is arrogant and well-connected and secure, he dismisses the extortion and sends assassins after the extortioners; they will arrive in 2d20 hours if not right now, from behind.
• if the target is not overcome with guilt, he will ask for proof. 
• If the PCs can provide it, fine.
• If the PCs can't provide it, he'll agree to pay half his adjusted payment. 
• If the PCs lie about being willing/able to provide it, now is the time for a bluff check. On a high result, he'll agree to the full payment. Otherwise, half. 
• If the target is shameless, no proof, no payment. On a medium bluff result, quarter payment.
• If the target is vengeful:
• If the PCs do nothing intimidating, the extorted will retaliate ASAP, before payment is made or during payment.
• If the PCs do something intimidating, the extorted will retaliate after payment is made, as soon as is feasible.
• If the PCs do something terribly intimidating, no worry about retaliation. 

The Payout

When the party actually goes to get the payout:

• if the target is vengeful and has not yet taken vengeance, 50/50 shot it's a setup
• if the target is not vengeful but is financially insecure, 50/50 shot he'll try to cut the payout by half; not taking the reduced payout makes target vengeful

Summary & Example

That is all backend information. Now you know the subject of the scandal, the target of the blackmail, how the target and subject are related, and how much the target is willing to pay. 

Example: using my preferred 4e NPC generator, I've got:

• Loge,
• an influential priest,
• as the subject and target of a scandal involving
• his participation in a meetup group for unspeakable activity in the Tombwood.
• That's a capital crime in Fallcrest.
• He's only social tier 1, but he's level 8 within that tier,
• which means his base payment is going to be (since he himself is the subject of the scandal) 1,750g (or ~ $175,000).
• Since the scandal involves a capital crime, the base payment is unmodified. 
• The PCs only have the testimony of a street urchin as proof (unreliable testimony) but are prepared to pay for a public ritual casting of Discern Lies on the kid while he tells his story. 
• The PCs knock on his door: they go to the temple and ask to speak with the subject himself. No problem there.
• When they make the proposal, I decide that he's not overcome with guilt, but he's not arrogant and well-connected and secure either; so he asks for proof. They're telling the truth about being willing to pay for the lie detection on the kid. I don't think of this guy as vengeful; so it looks like they're home free on this one.