Once a pickpocket, now a self-styled bandit lord in the Riverlands, Drennan's only concerns are gold and infamy.
Drenan used to be a thief in Oldtown, and was caught stealing jewelry from Gera Hightower several years prior to the events of the First Era. In return for his attempt at larceny, Gylen saw to it that the man paid an appropriate price, and was thrown in the dungeons to rot. Fortunately for Drennan, a Night’s Watchman plucked him from the burgeoning cells, and took him northward.
The bandit-to-be bided his time, escaped on the Kingsroad just after the Blue Fork, after slipping his chains and killing a black brother. He decided to remain in the Riverlands, an area ripe for plunder, where he created his criminal empire.
His motley crew were initially known as the Harroway Rooks, later the Dead Men as they grew in infamy, and after he killed a few rivals over the course of several years. Drennan himself played an instrumental role in the rise as a gifted thief - helped in no small part by the aura of invalidity that comes with being a cripple - a cunning pragmatist, and a ruthless leader.
The Dead Men started off as mere pickpockets, burglars and thieves, later turned their talents to extortion, blackmail, road tolls, highway robbery, smuggling, in some cases river piracy and raids on small unmanned settlements. They were known for wearing the armour of soldiers found dead, or slain in combat by their own hands - locals heard rumours of Dead Men rising from their graves to steal from them, visit terror on their families, and the name stuck. Some of them paint skulls and the like on their armour etc, to terrify their victims to silence in the face of authority. The bandits operate primarily on the Blue Fork between Fairmarket and Harroway.
They followed in the wake of the Burning Hand’s men in recent years until their demise, and managed to keep their operations relatively clandestine through a mixture of fear and violence when necessary.
All in all, there are approximately sixty members, including informants/pickpockets/burglars in Fairmarket, Riverrun, Harroway, several lightly armoured raiders specialising in combat, a few smugglers on the Blue Fork, and a fence in Harroway, who sells goods on thriving black market.
The Dead Men continue to conduct their operations, becoming bolder and bolder with the political instability still rife in the Riverlands. They stole a caravan from Brynden Frey's army, and took Howland Keath captive.
The Dead Men later abducted Alysanne Rogers and her daughters, holding them for ransom. The noble ladies were returning to the Stormlands after attending Brynden Frey's wedding to Alicent Baelish. Afterward, an abandoned village the Dead Men visited was riddled with the greyscale plague, and cost the lives of a significant number of the Dead Men.
Myranda Rogers was able to escape in confusion and ran into a patrol of Brynden Frey's men. The men gathered local villagers to form a small militia and rescue the Rogers and end the Dead men once and for all.