Taxes, who needs 'em! You don't that's for sure, taxes never did you a lick of good. Sure they pay for roads, but have you ever seen the roads? You grandma's chin is smoother than those roads and she hasn't shaved in weeks! Soldiers? More like goons. Those guys aren't there to protect, they are there to take. It's all a racket! Well you've found a way around all that. Half scoundrel, half hero, you are a bootlegger. You know all the back ways, side ways, and under ways, and exactly who's palm to grease to get your home brewed goodies past the taxman and into your grateful customer's hands.

Skill Proficiencies: Choose two from Deception, Athletics, Sleight of Hand, Stealth, Nature, Animal Handling, Insight, Perception, Survival, Persuasion

Tool Proficiencies: Vehicles (land), Brewer's Supplies

Equipment: A fancy leather vest or a pair of leather boots, a set of common clothes, and a leather pouch with 15 gp

Suggested Characteristics

In general, bootleggers value survival, and then profit, above other things. One could be a part of a larger organization, or might run a small still and smuggling route of their own. Bootleggers live the lies they have told, and they have a natural ability to recall all the falsehoods and half-truths they have ever spouted.

d8	Personality Trait
1	I love being on the road but hate walking
2	I think of everything in terms of monetary value.
3	I never stop smiling.
4	Nothing rattles me; I have a lie for every occasion.
5	I love gold but won’t cheat a friend.
6	I enjoy doing things others believe to be impossible.
7	I become wistful when the sun sets over a good campfire.
8	I am no common criminal; I am a mastermind.

d6	Ideal
1	Wealth. Heaps of coins in a secure vault is all I dream of. (Any)
2	Bootlegger’s Code. I uphold the unwritten rules of the bootleggers, who do not cheat their customers, only the taxman and his goons. (Lawful)
3	All for a Coin. I’ll do nearly anything if it means I turn a profit. (Evil)
4	Peace and Prosperity. I only do what I do to keep my community afloat. (Good)
5	People. For all my many lies, I place a high value on friendship. (Any)
6	Daring. I am most happy when risking everything. (Any)

d6	Bond
1	My best shine recipe was stolen from me, and I'll never forgive my rival who took it.
2	I intend to become the leader of the criminal network I belong to.
3	I owe a debt that cannot be repaid in gold.
4	After one last job, I will retire from the business.
5	I was tricked by a smuggler who stole something precious from me. I will find that thief.
6	I give most of my profits to a charitable cause, and I don’t like to brag about it.

d6	Flaw
1	Lying is reflexive, and I sometimes engage in it without realizing.
2	I tend to assess my relationships in terms of profit and loss.
3	I believe everyone has a price and am cynical toward those who present themselves as virtuous.
4	I struggle to trust the words of others.
5	Few people know the real me.
6	Though I act charming, I feel nothing for others and don’t know what friendship is.