May The Best Thief Win Quest Choices And Rewards

Joining the Thieves Guild in The Elder Scrolls IV: Oblivion requires proving your stealth and resourcefulness through a competitive trial called May the Best Thief Win. Assigned by the guild Doyen Armand Christophe in the Imperial City Waterfront, this quest pits players against two rival hopefuls, Methredhel and Amusei. Understanding the different paths, choices, and unlocked perks ensures a smooth initiation into Cyrodiil's criminal underworld.
Starting the Competition and Finding the Mark
After speaking with Armand Christophe during the midnight meeting in the Garden of Dareloth, you are tasked with stealing Amantius Allectus' diary. To locate his home, players can bribe a local beggar for information or follow Methredhel directly toward the Temple District. Acting quickly allows you to pick the lock, enter the house, and retrieve the target item before your rivals get to it.
Alternative Methods for Securing the Diary
If Methredhel reaches the house first and claims the diary, the quest provides alternative choices to secure victory. Players can pickpocket the diary directly from her inventory before she leaves or follow her back to the Waterfront District to steal it from her chest while she sleeps. Should you fail to obtain the diary altogether, Armand offers a second opportunity involving the theft of an antique cutlass from Rohssan's shop.
Key Guild Rules and Blood Price Penalties
Completing the trial requires adhering to strict faction rules established by the Gray Fox. Members are strictly forbidden from stealing from fellow thieves, robbing the poor, or committing murder while on a job. Violating the rule against killing innocent targets triggers a Blood Price penalty of 500 gold, which must be paid to Armand before full guild membership can be granted.
Quest Rewards and Unlocked Guild Privileges
Handing over the required item to Armand Christophe completes the quest and earns you official entry into the Thieves Guild. Successful completion grants access to Ongar the World-Weary in Bruma as a dedicated fence for stolen goods. Furthermore, it unlocks the Independent Thievery storyline and opens up special jobs that allow players to advance higher through the guild ranks.