Player freedom is one of the pillars of The Elder Scrolls franchise, and joining groups like the Thieves Guild is just one road available to potential adventurers. There's a guild in The Elder Scrolls for nearly every type of player: stout warriors can go to the Fighter's Guild, and those with more arcane fascinations can go to the best of the Mages Guild. Aspiring thieves can join the Thieves Guild, an organization dedicated to helping the people of Nirn burgle better. Each Elder Scrolls game has their own version of the Thieves Guild, but not all of them manage to be successful or have interesting plotlines.
Each The Elder Scrolls game's Thieves Guild serves two purposes. The first is to give the player access to fences, which buy stolen goods. Normal vendors will not buy anything gained through robbery, so a network of fences is needed to make money as a thief. The second is to give the player a thematically appropriate questline to follow. These questlines are where the guilds can shine or lose their thieving luster.
It's hard to quantify exactly which Thieves Guild is the best in the entire Elder Scrolls series, but there are some games that clearly give their guilds more interesting characters and questlines than others. When looking at each game in the franchise, there's a clear winner when it comes to the one Thieves Guild that epitomizes thievery in the best possible way. This incarnation is Oblivion's Thieves Guild, led by Gray Fox.
Why Oblivion's Thieves Guild Is The Best
Nearly everything the player does in The Elder Scrolls IV: Oblivion's Thieves Guild questline leads back to the Gray Fox in some way. Players first encounter the mythical figure in Wanted poster form, and, if followed through with, will be what leads the Hero of Kvatch to join the Thieves Guild. The stakes rise as players steal bigger and bigger things while climbing through the guild's ranks. Eventually, the hero meets the Gray Fox themselves.
The strength of this questline is in it's conclusion. As the player grows throughout Oblivion's Thieves Guild ranks, they eventually work together with the Gray Fox to pull off the ultimate heist; the theft of an Elder Scroll. Stealing an Elder Scroll is a very big deal in the universe of The Elder Scrolls. Besides being named after the series itself, these documents tell the story of creation myths, the present, as well as future events. Even though they can't be read through normal means without some severe side effects, just having one of these objects mark a person or organization as someone with some power. The heist itself feels like something straight out of an Oceans movie, with a fantastic build-up, infiltration, and eventual escape. As far as thieving goes, this final questline is the absolute height of what a thief can do in The Elder Scrolls universe.
Why Skyrim's Thieves Guild Is (Unfortunately) One Of The Worst
Skyrim's Thieves Guild questline is more subtle. It involves trying to rebuild a neglected guild, and eventually culminates in the Dragonborn getting revenge on the guild's leader. While there are some very cool moments in this questline (particularly the involvement of Nocturnal, one of The Elder Scrolls daedra), overall it feels less focused. There are two plotlines going on at the same time without giving much screen time to either, and as a result the story of Skyrim's Thieves Guild feels scattered and unfocused. If the questline spent more time on fleshing out the supernatural element, or focused more on the personal revenge story, perhaps things would've felt more impactful.
In the end, anyone's favorite Thieves Guild in The Elder Scrolls series comes down to personal preference. While some may prefer a grand final heist, others will love a classic revenge-based The Elder Scrolls tale. Players have a wide variety of burgling-based quests to experience, and this variety is one of the keys to The Elder Scrolls' success.