Smuggler
Skill Progression: Detecting noise is probably the most useful of the traditional thieves' skills for the Smuggler. After that, Hide in Shadows and Move Silently probably see a lot of use. Pick Pockets would be least utilized in smuggling.
Plans for hidden transportation may become elaborate. The trick is to be small and fast. Small makes it more difficult to find you; fast makes it likely that you can get through or, at least, get away, even if you are discovered. Sometimes the best smuggling routes go through treacherous territory or difficult terrain. This means that a Smuggler must be flexible. For instance, he may arrange to bring a canoe or even smaller craft to traverse a swamp or area of many small lakes and streams, portaging when necessary and leaving the canoe behind (and hidden, of course) when he has passed the natural obstacles.
If the Smugglers will pass through dangerous territory (plagued by bandits, humanoids or monsters, for instance), it is best to work out some means of protection: Either bring along a couple of thugs or mercenaries for the difficult parts, or pay "protection money" to the dangerous parties. Most bandits or humanoids, and even intelligent monsters, would be perfectly happy to let Smugglers through in return for a cut of their merchandise.
Or they may tell the Smugglers that they can pass safely through, and then renege on the deal.
For such a situation, it is best for the Smuggler to have some powerful muscle behind him - like a guild. A great many Smugglers are part of guilds. Guilds that operate in more than one urban center, or in the countryside, usually employ a number of Smugglers just to move people and items within their own networks. They may also have Smugglers who specialize in dealing with other guilds; such Smugglers should have a high Charisma, because they must serve as diplomats as well as businessmen. Finally, there are freelance Smugglers. They may operate between guilds, between guilds and freelance fences, or, on rare occasion, solely among freelance fences.
Remember that a Smuggler operates between fences; he rarely, if ever, deals directly with thieves or non-"wholesale" customers. The fence or guild works out deals with prospective buyer fences, and then hires the Smuggler to make the delivery.
Items from the "Evasions" section of the chapter on equipment are of great use to the Smuggler. Marbles (if the surface is right) or caltrops can do much to hamper pursuers, and aniseed or dog pepper can throw dogs off the trail.
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