Desperate Gambler

A Nord down on his luck who hides out in Windhelm’s barracks and pays the Dark Brotherhood to settle his problems in its repeatable contracts.

The Desperate Gambler is a Nord with no name, a bad habit and, apparently, someone he wants dead. He is one of the contractors for the Dark Brotherhood‘s repeatable murder jobs once the Brotherhood has been rebuilt.

Where to find them

He stays in the barracks of the Palace of the Kings in Windhelm. After handing out his job, he simply wanders the barracks until the deed is done.

Quests

The Dark Brotherhood Forever – the Gambler pays you a leveled sum of gold up front to kill one of the Brotherhood’s possible targets. Targets on this list include people like the Coldhearted Gravedigger. Do the job and he goes back to whatever it is desperate gamblers do.

Good to know

  • He is essential, so you can’t solve his problems by solving him.
  • He carries an iron sword and a copy of the book A Kiss, Sweet Mother.

Also in Windhelm

Race, level, class and factions read from the Skyrim game files; story details checked against community wiki articles and written in our own words.

Quests featuring this character

Places connected to this character

Windhelm is the ancient, snow-covered capital of Eastmarch and the Stormcloak stronghold – home of Ulfric Stormcloak’s Palace of the Kings and the Gray Quarter.

Factions

The Dark Brotherhood is Skyrim’s guild of assassins – the Night Mother, the Listener and a contract that could shake the Empire. How to join, the questline and rewards.

Weapons connected to this character

Armor connected to this character

Mentioned on these locations

Sources checked: Skyrim game files (NPC records, factions, read 2026-10-11); Elder Scrolls Fandom character articles