Crime Boss

From the time of their youth, they have worked to carve their own little realm from lawless space. The quintessential Boss lords over a small neighborhood in the poorest part of town, where the guard won’t dare to set foot. Others lead a band of merry outlaws who control a stretch of wilderness and maybe even a small village. Some have even been granted official authority, as the sheriff of a frontier town, commander of a small military camp or major of a small trade post.
While often brutal and attached to their turf, bosses are also exceptional individuals, with a strong drive and their own sense of decency. A boss that sees their position secured and their area under control is rarely content to sit back and enjoy the spoils. Most strike out to expand their influence and seek new challenges, bursting with confidence and always hungry for more.
A boss has power, but also responsibilities to their henchmen and retainers. To last in time, a boss must be tough, but also clever and diplomatic at the right time.

by Rob Taylor

Hobgoblin Boss

Type

Informal

Form of Address

Boss

Alternative Naming

Crime Lord

Boss 5e Background Info

Boss (Criminal Background)

Skill Proficiencies Intimidation, Athletics

Tool Proficiencies Vehicle (land), 1 gaming set

Equipment

• One set of slightly damaged fine clothing, with 10 sp sewn in
• One heavy gold chain
• Loose collection of simple and illegal contracts
• Crowbar or whip
• Finely decorated knife that belonged to someone dead
• Pouch with another 10sp

Features

King of the Hill
You rule over a small area of turf, such as a neighborhood, small settlement or a stretch of wilderness with a hidden camp. In your turf, the people are poor, but you and your friends can comfortably live of their work (and petty crime) as long as you stay in the territory, and maintain your grip. No one will dare report any crime you commit, and if someone else commits a crime, it will be reported to you instead.
Regular law enforcement won’t enter your territory. If you are wanted for a crime, no one will come for if it is a minor offense. Only independent agents, such as adventurers and bounty hunters, will come for you when you commit serious crimes. However, if you go overboard, there will be a raid with overwhelming force and you will loose the benefit of this feature for at least one week and possibly even permanently.

Traits

d8	Boss Personality Trait
1	I and my followers proudly wear the colors of my gang.
2	I leave a mark of my presence on every place I visit.
3	I bully the weak, but respect those that stand up to me.
4	I am obsessed with tasteless and showy accessories.
5	I am very loud. You don’t want me to lower my voice.
6	I want to be seen as one of the upper class.
7	The slang terms I use don’t make sense to anyone outside of my immediate area.
8	To stay sharp, I avoid indulging myself.

Ideal

d6	Boss Ideal
1	Perfection. Terror. Only fear can impose order and I intend to bring order wherever I go.
2	Redistribution. I take from the rich and give to the poor.
3	Home. I took control to improve the lot of those around me.
4	Loyalty. I do not give my word and friendship easily, but when I do, it is for life.
5	Audacity. The only thing stopping one from doing anything is lack of courage.
6	Anarchy. The only law is that the strong rule the weak and I aim to be the strongest.

Bond

d6	Boss Bond
1	Children, the sick and the elderly need not fear me.
2	There is only one person on my turf who dares to oppose me. That is why I am in love with them.
3	Nobody tells me what to do, except for my mum.
4	I always heap abuse on my most loyal henchman, but I would be heartbroken if something happened to them.
5	The source of my illegal income depends on people on the outside. I take care to keep good relationships.
6	This was once a peaceful and prosperous place. I cling to memories of those days and dream of their return.

Flaw

d6	Boss Flaw
1	My operation exists at the mercy of a bigger criminal organization.
2	My greatest secret is that I betrayed the previous boss to get my position.
3	I am in charge because everyone believes I did something very awesome or terrifying. Only I know that it was all a coincidence.
4	I am paranoid that someone might betray and topple me.
5	I really can’t take a joke at my expense.
6	We are involved in a ongoing feud with a similar group that could erupt in bloody war at any time.