Ahoy,
Ok,normally when traders were trading the goods that they were carrying wasn't always legal,they smuggled goods for extra gold coins. That could be implemented here,with a dialogue.For example:
"You are looking around the tavern when a "well dressed French man" approaches you and says, "Are you the infamous Captn Jack I've heard about from the tavernas?"
*You could go on to say*
Yes(Ah,I've some goods that I am trying to get to Tortuga would you be interested in transporting them?)
No.(Well mate,I am sorry but I must have been mistaken,sail safe.
Let me help you find the door. #Explains itself#
The story could be made more interesting as it progresses.
*THE OFFER*
Would you say $2000 to transport the goods to Tortuga?
*OPTIONS*
Yes
No
In a hurry?Double the fee!!(50% Chance of getting a yes/no)
*In some cases the dealmaker can give singled commands*
(I am willing to pay $4000 no more no less,take it or leave it )
Take it (+10 hostility to smugglers nation)
Leave it-*(+10♡ to governor daughter)
Also,you and the anonymous person wouldn't be of same nation.