Criminal Enterprise

A character creating and running a criminal enterprise spends free time between adventures orchestrating and performing crime for profit. Running a successful criminal enterprise requires gathering information, forging connections with criminal contacts, and greasing the appropriate wheels.
Criminal enterprise covers a workweek of planning punctuated by one major operation. A character must spend one workweek in a well-populated area and put forward at least 25 gp gathering resources to pull off a criminal operation.
Infamy Points

After a workweek of planning, a character makes an ability check using the Criminal Enterprise table to determine the number of infamy points acquired that week. If a character has infamy points when making this check, add the infamy point total to the check. The type of ability check a character makes depends on that character’s role in the criminal operation.

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The Brains.
The brains role is the mastermind behind the operation. The brains is rarely present when the operation goes down. A character filling this role makes an Intelligence (Investigation) check.

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The Lookout. The lookout role is the eyes and ears of the operation. The lookout is responsible for standing guard while the rest of the team completes the job. A character filling this role makes a Wisdom (Perception) check.

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The Face. The face role is the inside agent that uses charm to their advantage. The face has gathered valuable information and deployed resources critical to the success of the operation. A character filling this role makes a Charisma (Deception) check.

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The Thief. The thief role is the one getting their hands dirty. The thief is the team member that quietly slips in or out of whatever bars access to the operation’s target. A character filling this role makes a Dexterity (Stealth) check.

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The Muscle. The muscle role is the bruiser that backs up the team. The muscle is the team member that goes out swinging if the operation goes sideways. A character filling this role makes a Strength (Athletics) check.

Criminal Enterprise

Check Total

Result

1-5

The operation was a disaster. People got caught, things went wrong. It was a total embarrassment. You lose 1 infamy point. If you have no infamy points when you roll this result, you have disadvantage on the next check you make to determine infamy points.

6-10

The operation fell apart. No one got caught, but no one got paid. You gain no infamy points this week.

11-15

You hit a few snags, but you pulled off the operation in the end. You gain 1 infamy point.

16-20

The operation was a success. It went exactly to plan. You gain 2 infamy points.

21+

You pulled off the perfect crime, the operation went flawlessly, and you even picked up a little extra. You gain 3 infamy points.

Infamy points represent a character’s successful crime streak and street credit with the criminal underworld. A character can spend one or more infamy points to use the following features.

Acquire Crew Members (Costs 1 or more Infamy Points).

The character can call on others to help in an operation, reducing the chance for complications. Each point spent represents one extra crew member who helped performed the operation. The chance for a character to experience a complication after the operation is reduced by 5 percent for each point spent on extra crew members.

Get Paid (Costs 1 or more Infamy Points).
The character can fence stolen goods or otherwise get a payout for the committed crimes. The character receives 250 gp × the number of infamy points spent. The character must be in a populated settlement to use this feature.

Grease the Wheels (Costs 2 Infamy Points).

The character can call in a minor favor. Minor favors from the underworld are small actions that can make life a little easier for a criminal. The following are some examples of minor favors:

• Making sure a particular door at a particular place is left unlocked
• Ensuring a package is delivered quickly and quietly
• Bribing guards to look the other way for a minor offense
• Getting the location of a difficult to find person or object
• Securing a hideout and food for one week

Legendary Caper (Costs 5 Infamy Points).
The character can pull off a legendary caper, provided the character hasn’t performed a legendary caper in the last year. A legendary caper is the crown jewel of operations, and the character receives a significant amount from it. The character doesn’t need to roll for complications when spending infamy points to pull off a legendary caper. The character can choose whether to receive 10,000 gp or one uncommon or rarer magic item, provided the GM approves the item. The character must be in a populated settlement with wealthy individuals to pull off a legendary caper.

Complications

Characters who spend their time pursuing criminal enterprise have a high chance of becoming ensnared by complications. A character has a 25 percent chance of triggering a complication for each workweek spent pursuing criminal enterprise. When a complication is triggered, the GM can create a complication or roll a d8 and consult the Criminal Enterprise Complications table.

Criminal Enterprise Complications

d8

Complication

1

One of your accomplices was caught. Either pay 250 gp to bail them out of jail or lose 2 infamy points.

2

Your information was bad, and the merchandise was worthless. You can’t gain infamy points this week.

3

There’s a new sentry or watchman in town, and they’ve become obsessed with bringing you down.

4

A new thieves guild has popped up, and their blundering mistakes are bringing heat down on the whole underworld.

5

Another criminal is taking credit for your operations. Lose 1 infamy point.

6

You were sold out by one of your own. Either pay 100 gp for each infamy point you currently have or spend a week in jail for each infamy point you have.

7

You intruded on a crime boss’s turf. You have disadvantage on the check to determine your infamy points this week.

8

You caught word of a golden opportunity. You have advantage on the check to determine your infamy points this week.