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Message: <blockquote data-quote="BlackMoria" data-source="post: 679618" data-attributes="member: 424">Let him play his game..... then show him that actions have consequences.Situation 1:  He precedes to loot the town.  You said everyone has left except the military.  Except the military in all probably has implemented martial law and looters are subject to summary justice - military tries to apprehend or kill him.  Character is question either flees or fights.  Let the chips fall where they fall....Situation 2:  Tell him it will take several hours to find something worthwhile to loot.   Meantime, the advance scouts or the actual army of the bad guy shows up.  Party now must flee or fight.  And if they flee, let them know that the loaded wagon of the PC 'who rather be merchant than hero' is slowing down escape.  He either leaves the wagon (and horses) and his loot or the foes overtake them.In short, if the character wants to play merchant, let him.  Then crock him with some savve dude selling him bad or defective merchandise, bandits rolling the 'merchant', bad debt, merchant rivalry and the hundreds of other things that plague businessmen.  Then see if he is still game to be 'Marco Polo'</blockquote>