Spies upon the road discover the heir of Durin

Camped in the dark woods near the west gate of Bree three men the from the wild wait for a party of dwarves expected along the east road.

As nightfall descends upon the woods, a loud singing can be heard…

These three men are bounty hunters in the service of a man cloaked all in black, who came from the east across the Misty Mountains in the fall of last year asking about a dwarf named Oakenshield. This hooded man proclaimed that he was in the service of one who would pay a kingly sum to any who could bring him the head of this wretched heir of Durin.

A bounty was given, written in the Black Speech which proved to the three men that this stranger was he was indeed working for the dark power across the mountains. These hunters along with others began to scour the lands along the road looking for this dwarf for the better part of a year.

The dark man from the east had at first promised gold, but as times passed he began to threaten them, finally promising a slow and cruel death to any who might betray his Master, the Necromancer of Dol Guldur. Even here in the west of Middle-earth that name summoned a deadly fear. He told them that no more than a days march from Bree, were orcs from Mount Gundabad who would come upon them in their sleep, slit their throats and eat them, if they did not soon track down the elusive dwarf!

Now the men wished only to find this Oakenshield, so that this dark man would return from whence he came and leave them in peace. A little robbery and an thevery was all they wanted, this dark man with his strange speech filled them with a nameless fear. They want to be rid of the dwarf and those who hunted him.

Oakenshield had been seen in Bree alone, not more than six months before, but he had slipped away before he could be captured. Since then the east Road has been watched by spies for any dwarves traveling in the land.

Finally a message came from one they paid to watch the roads in the west, with news that a company of dwarves was on its way to Bree and that one among them was none other than Thorin Oakenshield. For three days they had camped beside the road waiting for the dwarves.

As night fell on the third day, the sound of singing could be heard in the distance. Along the road came merry band of travelers upon ponies, singing and talking loudly with no care for who might be listening. As the party passed them by, there was one who brought up the rear, taller and riding on a horse. He looked directly up into the woods were the men were hiding. There was no way he could have seen them in the deepening gloom as night came on, but the hidden ruffians got the uncomfortable feeling that this travel in grey knew they were being watched.

The company of dwarves was too large, to try and take Oakenshield in the open, so they held back and followed them silently as they entered Bree, heading to the Prancing Pony no doubt. The company of dwarves along with a small hobbit and the tall stranger, who they soon discovered was the wandering grey wizard the had hear tell of.

The dwarves stayed at least a week in Bree, gathering supplies for a long journey into the wild. This was good news to the three ruffians, but they also learned that the entire group was planning to go east together. There was no way they could enter the camp of such a large group and take the head of Oakenshield without a fight. They decided instead to try and sell this information to the dark stranger from the east and be done with it.

The three Ruffians went to meet the dark man from the east who was camped along the road east of Bree. They did deliver their message, though they were never seen  or heard from again in Middle-earth.

The Mordor Appendices ~ The Time Line of the Year 2941 ~ 2942