Many stretches of high road in the Central Kingdoms? were once roamed by gangs of bandits intent on robbing, pillaging travelers. Much harm came to from this. Several years ago, the reign of Jearden Threetoes I?, an effort was made to be rid of the bandits. Much of the banditry was slain until they organized and made stout resistance.
Jearden, seeing his reign closing soon, and knowing the next Monarch may not have the will to see so much blood shed over this subject, sued for peace among what organization existed with the bandits. Secretly, he issued them a Warrant and Charter as the Loyal Order and Association of the Gentlemen of the Highway. The mean part of this comes from unusual political, traditional and practical concerns. The Highways of the Realm are owned by the Monarchy, and with most of the lands of the Monarchy, they are given out for some term greater or less to a Lord. The Lord must pay a quitrent to the Crown, but is otherwise free to earn what he may from the land so granted. The highways should fall under a similar jurisdiction, but their easement upon each lord and town's land, and the baseness of collecting a toll make it nearly impossible to find a lord willing to accept them. Of course, outright hiring one of the many peasant operations to do so would be quite beneath the Crown, and the Crown having a stout guard, saw no reason to affect a change in the operation of these roads.
This uneasy arrangement went on for some time, until it became clear to those of mean character that these highways were and seemingly always would be unguarded, and an easy field to plow for rich treasures. This low situation continued until it became clear in Jearden's reign that the banditry was causing an undue disruption in trade and communication.
In Jearden's reign then, the Company was nominally organized to inveigh against disorganized banditry, but was Chartered secretly so as to not blemish the person and civility of His Majesty or the Crown. As such, and although their rates were set, the Order's members often charge too steep a price, and still from time to time molest the persons of travelers on the road. On the whole, however, the roads are now privately maintained by the Order, and much safer, or at least the banditry upon them is much more predictable, and has much less bloodshed, except for a few occasions when cooler heads do not prevail. At either case, the Order is bonded against local Healers and Judges for suing cases and resolving these issues in satisfactory manners.
Although secret, the Warrant for the Order is a legitimate Crown Charter, and many a brazen or foreign traveler has found themselves quite put out upon suing and losing their cases before the Judges of the Wetlands.