Knife blades and harness buckles smeared with black soot; muffled oar-locks and a moonless, midnight-rendezvous, torchlights on the moors and signal lights beyond the breakers . . .

Throughout the ages and across civilizations, there has and will always arise the inevitable desire, demand, even desperate need, for those things regulated or forbidden. These desires and demands, in turn, frequently spell opportunity to an entrepreneurial few. Individuals like you, who—despite oppressive laws, exorbitant taxes, or religious or political creeds—have ventured to make available to many what some would see reserved for the few.

Perhaps you bootlegged monastic whiskey down secret mountain paths, spiriting them away to richer markets abroad. Or did you hone your craft duping city watchmen and tariff inspectors, moving shipments of stolen art, antiquities, or even people under their very noses and into their beloved city? Possibly your motivations rose higher and you rowed ashore through storm and darkness to bring weapons and supplies to desperate revolutionaries? Or evaded murderous bounty hunters, while escorting escaped slaves along forgotten caravan tracks in a last-ditch bid for freedom? In any case, you have left in your wake a colorful trail of bribed customs officials, befuddled border patrols, and “missing” tax collectors. All in all, not bad seeing you have only just begun to (re-) make your name in the world.

Skill Proficiencies:  Deception, Persuasion

Tool Proficiencies: One vehicle proficiency of your choice (land or water), and choose one from navigator’s tools, disguise kit, or forgery kit

Equipment:  A set of tools (matching your tool proficiency choice), a hooded signal lantern, dark traveler’s clothes, and a leather belt-pouch containing 5 gp

Feature: “Even I get boarded sometimes.” As a master of contraband logistics and camouflage, all Intelligence (Investigation) and Wisdom (Perception) checks made to discover items that you have hidden on a person, vehicle, or pack animal are made at disadvantage. If the characters conducting the search can hear you, you can oppose their checks with a Charisma (Deception) check.

Additionally, you have advantage on Intelligence (Investigation) and Wisdom (Perception) checks made to discover the concealment of goods or items on a person, vehicle, or pack animal.

Suggested Characteristics: Often well traveled and worldly, those who take up the smuggler’s life are usually acute observers and mental note-takers, with a knack for numbers and a gift for smooth (fast) talk. Their adrenaline-fueled lifestyle of danger, intrigue, and constant vigilance has left more than a few with some “colorful” and noteworthy personality traits.

d6        Personality Trait

1. I am a natural gambler; prone to risking it all if the pay-off seems exciting, amusing, or lucrative.
2. Among the first things I do when arriving at a new place is begin to collect information and establish contacts to “feel out” the import-export potential of a place.
3. I tend to be vigilant about covering my tracks, checking for tails, knocking on walls, and so on.
4. My long association with persons of dubious character has made me slow to trust or make friends.
5. I hide my origins and history under a shroud of absolute secrecy. So much so that I haven’t used my real name in years.
6. I have an appraiser’s eye; I am frequently found assessing the wholesale and logistics values of almost any type of potential “swag” I come across.
7. In-depth planning and organization, security and reconnaissance details, time tables and signal codes—I am a preparation perfectionist. I leave little to chance.
8. Some might consider me cold or aloof. I am quiet, but supremely confident in my own abilities; I rarely rely on others for anything.

d6        Ideal

1. Self. It’s nothing personal, truly. Just don’t ever get between me and anything I need. (Neutral)
2. Benevolence. Sometimes, bending a few rules and breaking a few laws is necessary to help those in need. (Good)
3. Efficiency. Proactive thinking and organization, inventory control, balanced books and timetables—these are the tools of a successful life. (Lawful)
4. Cupidity“Greed is right, greed works, greed clarifies.…” (Evil)
5. Easy-Rider. My lifestyle will never be dictated by the borders, rules, or the laws of others. (Chaotic)
6. Aspiration. Someday I will be a ship or caravan master and blaze my own trails and trade routes to wealth and adventures as yet unheard of. (Any)

d6  Bond

1. My word is my bond; I have never welched on a deal, dishonored a handshake, or double-crossed a partner.
2. I am hastening to pay off an old debt, which could have assassins put on my trail any day now.
3. A corrupt magistrate ruined my good name and drove me underground; soon I will have my revenge.
4. Ill-gotten or not, a goodly portion of my gains goes to the humble, little monastery and the brothers there, who took me in that terrifying night so long ago.
5. I am known to have been a witness to a horrible crime. I became a smuggler as a means to survive while remaining in hiding from the crime’s perpetrator.
6. I will do whatever I must to prove my superiority and to discredit or destroy a past associate, who has turned into fierce rival.

d6  Flaw.

1. I am an obsessive haggler; from coppers for the shoeshine boy, to the uncut emeralds for the latest harbormaster’s bribe, I never settle for first price.
2. I always take a cut, skimming a small percentage off the top of almost anything I handle.
3. Some think me paranoid because of my hyper-acute awareness and sense for spies, eaves-droppers, and imposters, magical or otherwise
4. I’ll go a long way to win the favor of the local beauties and fine-featured folk.
5. My loyalties go to the highest bidder or most lucrative contract, regardless of personal feelings or desires.
6. I mentally figure out the net worth of people in terms of liquid assets.