You find dirt on people: embarrassing drama, reportable crime, sordid affairs, political corruption--nothing's necessarily off limits. You have a way of hearing things not meant for your ears, and seeing things not meant for your eyes. What does this leverage buy you? Gold? Favors? Status? It all depends on what you discover, who you're dealing with, and how much credible risk you represent. Fact check twice, threaten once.
- Skill Proficiencies: The skills you need to gain info and sometimes connect the dots. Choose two of the following: Deception, History, Insight, Intimidation, Investigation, Sleight of Hand, Stealth.
- Tool Proficiencies: Pick two of the following: Disguise Kit, Dragonchess Set, Forgery Kit, Thieves' Tools,
- Languages: Choose two languages of your choice.
- Equipment: A notebook and some pencils, a small bag of coins containing 65 gp from successful, previous blackmail, a easily concealable dagger, a list of your previous alias names, a crowbar, 50 feet of hemp rope, and a pair of gloves.
Whether you collect your blackmail through gaining confidence and deception, or through investigating private documents, you frankly don't care. You aren't particularly concerned with how you find leverage, but rather how you will use it.
Whenever you succeed on an investigation check while going through a private area, roll a d100. Similarly, whenever you succeed on a Charisma check to gain someone's confidence & trust, roll a d100 as well. If this d100 result is equal to, or less than, your current character level, you are able to pick up on a bit of juicy information. Is the information worthy of blackmail? Well--that's up to you. Finding multiple pieces of evidence and/or eliciting multiple confessions will help apply more pressure when the time comes to confront your target.
Confronting your blackmail target is as simple or as complex as you make it. Upon making your threat, you make your Charisma (Intimidation) check. Consult the following chart in order to determine any additional modifiers.
| Pieces of Damning Evidence | Blackmail Intimidation Modifier |
|---|---|
| 1 | No additional modifiers. |
| 2 | +3 bonus to the result. |
| 3 | Advantage on this Charisma (Intimidation) check |
| 4 | Advantage on this Charisma (Intimidation) check, +3 bonus to the result. |
| 5 | A result on the d20 of 14 or lower is now considered a 15. |
| 6 | Your result becomes a natural 20. |
Just as the player should feel empowered to roleplay as a blackmailer, the DM should feel empowered to play as a blackmailed victim. Some people will respond with their own threats, or just rush to violence. Even if you succeed on your final blackmail Intimidation check, and get what you want, there's no telling if they'll seek revenge.
As far as the demands of blackmail go, the demands can be pretty much anything--though not all victims will be capable of providing the demanded service or good. For example, if you ask for 25,000 gold from a corrupt village mayor, he might sheepishly hand you a pouch of gold worth only 100 gold. You might demand someone fight on your side, but if you turn your back for too long, there's no promises they won't flee. If you blackmail a king--well good luck with that. My point is: the player and DM need to agree to play out these likely tense situations where reality doesn't always meet expectations. Blackmail doesn't always go according to plan!
As always, the DM is allowed to set the DC of any & all checks. That said, I recommend increasing the DC to find & collect juicy information based on who the player is targeting. A mob-boss, kings, religious authorities, all probably keep their secrets locked down pretty well. Local business-owners, small-town officials, and young & gullible might overlook their security. Again, point is, set the DC based on the target.
Lastly, I wouldn't limit evidence to just Investigation and Persuasion checks. If a player were to use magic to spy, like with a Scrying spell for instance, seeing the target make a shameful, blackmail-worthy decision ought to count as evidence--if you have a way to share that scene (aka via the spell: Encode Thoughts). Reading lips with the Observant feat should also allow a player to collect evidence too. If a player has a creative way to find leverage, I vote let them do it.
Suggested Characteristics
Any alignment.
Contacts
As an option you may choose any contacts from the table below or alternatively roll a d4 and consult it. Alternatively, you may create an entirely unique contact if you so wish.
| d4 | Contact |
|---|---|
| 1 | A guard who works with you. |
| 2 | A mentor who has blackmailed you. |
| 3 | A previous victim of your blackmailing. |
| 4 | A current blackmail target you've started to investigate, and/or gain the confidence of. |
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