I have been debating on joining the thieves guild lately and cant decide what to do. My main interest comes from access to the Nightengale equipment and trainers along with just doing something different. The problem is they dont seem to be like what they were in Oblivion so I am having a hard time convincing myself that it is worth it. They seem far less like a band of social outcasts with a good heart and loose fingers and seem more like a mafia or group of ruffians and thugs. If there was a faction for joining the guard or something like that I would do it but sadly there isnt (or at least currently isnt).

Can someone elaborate on the thieves guild and the spectrum of morality it covers without spoiling major plot points if at all possible. I am not expecting to be running around saving kittens from trees, but even after just the initial quest where you act as this thug extorting money from the people of riften, I felt like a complete tool and not like swashbuckling style thief.

If i am completely off base and they really are more free spirited and kind but I just need to get into it then I would like to know, at the same time if they really remain a bunch of heartless and greedy thugs then I would also like to know that.

the guild has pretty much lost its way, you have to make tham a group to be feared again in the other holds.
not kind as such (they are thieves) just maybe abit desperate.
i see them as kinda in the middle, on the one hand they arent against the idea of roughing people up, on the other they do what need to do to survive, its all they know.
the nightingale gear is quite good (if you are already a dark brotherhood member, then its good for that to)
i guess if you play a good person your mindset would be not do this questline.

I'll try to keep the spoilers to a minimum, but some may leak out as I try to elaborate.

You can fail the first action (get caught) and still get in.

The 2nd action is grey because I'm not sure if we're extorting protection money or collecting debts from loans. You'll get some negative comments in passing from the 'victims' afterward.

For the small jobs: you can refuse any of them if you don't want to victimize a particular mark that you like. You get "Failed" quests in your log, but there are no real consequences.

The Special jobs are kinda' grey also because some of the contacts are asses.

All-in-all I wouldn't consider the TG evil, but they aren't angels. And, yes, they are kind of a syndicate.

Sorry if I spoiled too much - I was just trying to give you some info before you get too far into the questline.

Honestly, I started with a "good" character, and after finishing the Theives Guild, I didn't feel "good" any more. It wasn't like in Oblivion where they were still likeable. Plus they treated "me" rudely the whole time I was out running around doing their dirty work! LOL The rewards are pretty good, but I didn't really like the guild or any of it's members. To me, Dark Brotherhood at least felt like a family, and I thought the rewards were better. I also got extrememly bored with the little side jobs you had to do to become Guildmaster. I wouldn't do it again. Just my opinion, of course.

Let's consult dictionary.com

Thief: [theef]; a person who steals; especially secretly and without open force; one guilty of theft or larceny

Origin: before 900, Middle English; Old English theof

Synonyms
burglar, pickpocket, highwayman. Thief, robber refer to one who steals. A thief takes the goods or property of another by stealth without the latter's knowledge: like a thief in the night. A robber trespasses upon the house, property, or person of another, and makes away with things of value, even at the cost of violence: A robber held up two women on the street.

Note that Robin Hood isn't mentioned in any of the above... stuff. Note that stealing (shockingly) the property of others seems to be an overriding theme of what a thief is. According to Hamurabai's Code, stealing was a crime. And as far as I can tell, it remains so in every known society on the planet. This leads one to the logical conclusion that thieves aren't the most moral of entities. So if going through the motions of taking things from imaginary characters in an imaginary world presents serious qualms, then Thieves Guild may not be up your alley.

The early thieves guild quests are both boring and definitely not nice. I did like the Nightingale parts though, and the armor is very cool looking. I would suggest doing it at least once. If you're running out of things to do with your current character and don't feel it would fit his personality, you could always start over with a less moral stealth type character.

*sigh* I miss the old thieves guild. Now they are a bunch of douchebags and superstitious nutjobs....

Nocturnal has *always* been the patron of the Thieves Guild. Ever wonder where the term "shadow hide you" comes from?

The first two Thieves Guild quests require putting an innocent man in jail on a pickpocketing charge (mind you, he's intended to be released shortly thereafter, but doesn't due to a bug). The second quest requires extortion, but if you don't feel like threatening or smashing heirlooms, you can brawl two and the rest will give in. They all pay the money in full. Some of their protestations ring a little false when you think about it (Haelga has a full bunkhouse -- how does she not have money, unless she's been spending extravagantly on her hobby? Keerava's inn gets business every day, and is frequented by the Black-Briars and the Snow-Shods, the richest families in Riften. Bersi I could legitimately see as not having money from business).

From then on, quests deal with internal affairs. Fourth quest requires putting a man in jail as well, though his ethics are a little skewed. Fifth requires minor thievery and technically, condoning embezzlement. The rest involve trespassing at the worst, and though it's *possible* to cut a bloody path through the guards and owners, it's not required.

The generic thievery missions are cut-and-dry, and technically thievery, but you're stealing gem-encrusted solid gold decorations from people who can afford the loss (well, sometimes weird things happen, like a peasant's house marked with a "no loot" shadowmark being a target).

Two of the special jobs are things that could have easily been "good guy" quests. The other two have you free a felon (though you never meet him and never hear how the murder he committed occured) and frame a pirate.

I am doing the same thing in Skyrim that I did in Oblivion: I played a good character up until L 48 or so. Now, for a break, I am playing a character who is not so nice. Have joined TG and am trying to join DB, but the dude won't visit me after I killed Grelod (SP?)
Point here is: If you have a really good character, don't use him/her in the factions where you have to do really bad things. Most good people would refuse. Ergo, start a new character.
Just a thought.

Put it this way. It's an occupation. You're a thief at work, but can always play the good guy at home.

Did you return to the kid in Windhelm and tell him it was done? IIRC the quest doesn't advance unless you do that, and it has to be marked as complete before the DB makes contact. Even then there is usually a bit of a wait time before you get a warning (I think it's 24 hours in-game, minimum). After that you must sleep somewhere or I've been told using the Wait function will also trigger the next step in the process.

tbh, at the point where you start the thieves guild I can't really blame them, the live in an impoverished, crime-ridden town (not just them) basically run by one woman, who they have to bend to if they want to survive. As well as this they can barely afford to feed themselves at the start and don't even have any money to give to the poor, furthermore they have lost all of their respect and so beggars may not even be all that compliant, as well as them being run by a complete [censored]. I like to think that at the end the thieves guild will start to help out the poor some more. Maybe part of a dlc or something?