The Elder Scrolls IV: Oblivion Remastered brings the iconic RPG back to life with enhanced visuals, improved mechanics, and the same immersive world that captivated gamers years ago. Set in the sprawling province of Cyrodiil, Oblivion invites players to craft their own legend, whether as a noble hero, a cunning mage, or a stealthy thief. One of the most thrilling questlines in Oblivion is the Thieves Guild, where stealth and wit reign supreme. The May the Best Thief Win quest is your gateway to this shadowy faction, challenging you to prove your skills in a high-stakes competition. At gameoblivion, we’re diving deep into the may the best thief win oblivion quest to help you navigate this sneaky adventure. This article was updated on April 29, 2025, to ensure you have the latest tips for Oblivion Remastered.
Getting Started: Finding the Thieves Guild
To kick off the may the best thief win oblivion quest, you first need to track down the Thieves Guild. This secretive group operates in the shadows of the Imperial City’s Waterfront District. The easiest way to start is by investigating rumors about the Gray Fox, the guild’s elusive leader. Speak to beggars like Simplicia the Slow in the Market District or Puny Ancus near the Waterfront. For a few gold coins (usually five), they’ll point you to the Garden of Dareloth, where the Thieves Guild holds midnight meetings. At gameoblivion, we recommend saving your game before heading to the rendezvous to prepare for the timed challenge ahead.
Once you arrive at the Garden of Dareloth at midnight, you’ll meet Armand Christophe, a doyen of the Thieves Guild. Choose the “Gray Fox” dialogue option, then “Join the Thieves Guild” to trigger the may the best thief win quest. Armand explains that three recruits—you, Methredhel, and Amusei—are vying for a single spot in the guild. The task? Steal Amantius Allectus’ diary from his home in the Imperial City and return it to Armand by the next midnight. This is where the may the best thief win oblivion challenge gets intense, as speed and stealth are your greatest allies.
The Race Begins: Locating Amantius Allectus’ House
As soon as you finish speaking with Armand, Methredhel sprints toward the Imperial City’s Temple District, where Amantius Allectus lives. She already knows the location, giving her a head start in the may the best thief win oblivion race. You have two options: follow her or find the house yourself. Following Methredhel is the quickest route, as she leads you directly to the eastern part of the Temple District. Alternatively, you can ask a beggar like Puny Ancus for Amantius’ location, which marks the house on your map for five coins.
At gameoblivion, we suggest following Methredhel if you’re confident in your speed. Her path is straightforward, but don’t get too close—she won’t attack, but you’ll need to beat her to the prize. Amantius’ house is easy to spot: it’s the first building on the right when entering the Temple District from the east. The may the best thief win quest hinges on timing, so don’t dawdle. Stock up on lockpicks from Armand (five gold each) before you go, as you’ll need to pick a Very Easy lock to enter the house.
Inside the House: Securing the Diary
Once you pick the lock and enter Amantius Allectus’ house, the may the best thief win oblivion quest becomes a race against Methredhel. The diary is hidden in a desk on the right side of the main room, tucked under a cloth tapestry near the basement stairs. Sprint to the desk and grab the diary before Methredhel reaches it. If you’re fast enough, you’ll claim the prize and get a quest update to return to Armand. Be cautious—Amantius may be home, so sneak to avoid detection and a potential bounty.
If Methredhel beats you to the diary, don’t panic. She’ll exclaim that it’s hers and flee to the basement, escaping through the Imperial Sewers. At this point, the may the best thief win quest offers a second chance. Head to Methredhel’s house in the Waterfront District, right next to the Garden of Dareloth. Wait until she’s asleep (typically until noon) and pick the lock on her chest near the door to steal the diary. Alternatively, with a high Sneak skill, you can pickpocket the diary from her before she escapes the house. Gameoblivion tip: Save before attempting to pickpocket, as getting caught can complicate the quest.
Handling Bugs and Glitches
Oblivion Remastered has polished many aspects of the original game, but the may the best thief win oblivion quest can still encounter bugs. One common issue is Methredhel failing to deliver the diary to Armand, especially if she grabs it on the last day of the in-game month. If this happens, you may need to wait several in-game days for Armand to offer an alternative task: stealing Rohssan’s Antique Cutlass from A Fighting Chance in the Market District. This backup quest involves picking three locks and avoiding a guard dog, so bring plenty of lockpicks.
Another potential glitch involves Amusei, who may get stuck in Castle Leyawiin’s dungeon if you pick the lock of his cell before starting the may the best thief win quest. This can break the Thieves Guild questline entirely. To avoid this, steer clear of Leyawiin’s dungeon until you’ve joined the guild. At gameoblivion, we recommend installing the Unofficial Oblivion Patch, which fixes many of these issues for a smoother experience.
Returning to Armand: Joining the Thieves Guild
With the diary in hand, return to the Garden of Dareloth at midnight to meet Armand. Hand over the diary to complete the may the best thief win oblivion quest and secure your spot in the Thieves Guild. Armand will welcome you as a Pickpocket, granting access to fences who buy stolen goods and unlocking the Independent Thievery quest to track your fenced loot. The Thieves Guild’s rules are strict: no stealing from guild members, no killing on jobs, and no harming beggars, who are under the Gray Fox’s protection.
If you fail to get the diary, Armand offers the Rohssan’s Antique Cutlass task as a redemption chance. Break into A Fighting Chance at night, pick the locks on the front door, upstairs door, and a chest in the bedroom, and grab the cutlass. Avoid the guard dog by sneaking or moving quickly. Return the cutlass to Armand to join the guild. Gameoblivion pro tip: Use the Skeleton Key (obtainable later in the game) or Open spells to make lockpicking easier in this backup quest.
Tips for Success in May the Best Thief Win
- Prepare for Stealth: Boost your Sneak skill before starting the may the best thief win oblivion quest. Wearing light armor or the Dark Brotherhood’s Shrouded Armor (+10 Sneak) can help.
- Stock Up on Lockpicks: Always carry extra lockpicks, as breaking one during the house entry can cost you the race.
- Save Often: The timed nature of the may the best thief win quest makes saving crucial. Save before entering Amantius’ house and before pickpocketing Methredhel.
- Avoid Combat: Killing Amantius or your competitors violates Thieves Guild rules and may incur a Blood Price, requiring you to pay a fine to continue.
Why This Quest Matters
The may the best thief win oblivion quest is more than just a trial—it’s your introduction to the Thieves Guild’s thrilling world of stealth, heists, and intrigue. Completing this oblivion quest unlocks a wealth of benefits, including access to unique gear like the Gray Cowl of Nocturnal and the Boots of Springheel Jak. It also sets the stage for iconic Thieves Guild missions like Untaxing the Poor and The Elven Maiden. At gameoblivion, we love how this quest captures the essence of being a master thief, blending challenge with the freedom to approach it your way.
Whether you’re a veteran sneak or a newcomer to Oblivion Remastered, the may the best thief win quest is a must-play. With our oblivion guide, you’re equipped to outsmart Methredhel, secure the diary, and claim your place among Cyrodiil’s sneakiest. Keep exploring gameoblivion for more tips, walkthroughs, and updates on your favorite oblivion quests!
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