Highway Robbery

From the introduction: Rodrick Pellingham, an orc by birth but raised by a wealthy human nobleman, leaves the city of Freeport to seek adventure and riches. Unfortunately, his idea of excitement is to assume the role of a swashbuckling highwayman. He approaches some high-ranking members of merchant concerns he’s met through his father — men he thinks are crooked enough to listen to his scam. In return for information on caravan routes and shipping manifests, Rodrick and a band of raiders will strip the caravans of their goods then quietly deliver their contents to the corrupt merchant barons. The merchant concerns collect insurance from moneylenders for the goods lost to banditry then unload the “stolen” goods on the black market for grossly inflated prices. The merchant barons line their own pockets twice over, while the raiders get first pick of the loot and a cut of the black-market rates! The crooked merchants readily agree, taking steps to conceal the plan from their own companies.