I recently created a thief, and I can't decide what direction I want to take him in.

When I've created thieves before, they've usually been of the eloquent, roguish-charm type, and I usually make a Wood Elf or Dark Elf.
This time though, I wanted a really gritty thief, one that definitely isn't afraid to get his hands dirty. So I've got a Khajiit male. I dont want him to go down the Assassin's Guild route, although if something happened to him in game that pushed him that way, he may join. My intent for now though is that he does not join.
His motivations are mostly selfish. He will do pretty much anything for gold, hence why he's gone the thief route. He robs citizens and has many brushes with the guards. More recently, he's discovered ancient tombs and the like, and quite likes to loot those. They are worth far more than people and houses, but the risk is much higher.

So he's got into a fair few scraqes. A lot of the time he's had to run away, and I like that. He definitely can't go toe to toe with most things. He will sneak past most things, preferring to avoid conflict, but if his obstruction in a ruin etc can be taken down with a few shots, he'll do that. If it's something pretty tough, he's quite happy to leave it alone.

My question is, should he join the Fighters' Guild? Right now, and for his background, he doesnt really suit the guild. But he will do pretty much anything if the price is right, and my thinking is that once he's robbed a few tombs and faced what they have within, he will probably think "how hard can this fighter stuff be?". He will figure that he can outsmart most of the guild members there and rather than fight his way to an objective, he can just sneak around to it with the minimum of hassle.
The other option is that the fighter thing isn't really for him, and that it's too far out of his role. Reason I'm questioning this is because my past roles have been very delicate thieves, good for cutting purses but definitely not up for much of a fight. This guy though is more mercenary than anything. So he's not really a thief by profession, but rather one out of necessity. If there was higher paying work, he'd take it.

As for his alignment, definitely neutral, but with a touch of "why should I care?". He'll take quests from other people if there is a decent reward, or if it opposes any guards etc, who are always a thorn in his side. So the corrupt guard style quests are fair game. As is the Thoronir one in the Imperial City, because there is both fair reward, and a certain amount of interest because clearly by investigating these dodgy traders, he might learn a thing or two, and maybe put the competition out of business in the process.
So, quests where some disgruntled guy wants someone dead because he's angry, that's a no. Likewise anyone in distress that needs a helping hand, that's their problem unless they cough up gold.


*Edit - having re-read the above, I know it doesnt read well and gets kind of repetitive and circles back on itself etc. Welcome to my brain

If he's more mercenary than thief, I might go for the Fighters Guild if I were you. It's not exactly out of character for a character like the one you described, but at that point I would stop calling him a thief (or at least a pure thief, he could still be a stealth-based mercenary, for example). If he does anything for the highest bidder, the Fighters Guild is good - you don't necessarily have to be a light side character to justify ranking up in the Fighters Guild. And they pay you. Which is always nice.

Regarding Fighters Guild, I don′t see that as the first or even second stop for a thief. Mages Guild would be better, for the sole purpose of making chameleon spells and open lock spells. If you don′t consider that cheating of course but I think I read he′ll do anything for gold so..

The Mage's Guild is way out of context for this character I think. He has absolutely no magic skills. Not even taking that into account, he can sneak and pick locks just fine, so really no need for Chameleon and Open Lock.
Doing anything for gold is fine, but doing something for gold that he can already do for gold and isn't mentally capable of the other option is something else entirely.

There is a Thieves Guild, you know.... Did you mention that, because there is a verrrry good chance I missed it.

This. Why are you joining the FG? Why not join the TG.....?

Here's my suggestion:

Join ALL guilds. I mean it.

Pretty much, if I were to guess your alignment is 'Chaotic Neutral". You're pretty much an outlaw, mercenary. The higher pay gets you, meaning if the Thieves guild hires you to rob a Mage, but said Mage catches you in the act and proposes a better deal against the Thieves guild, you'll take it.

Now, why join all guilds? you said many of your former builds were 'eloquent', etc... I may be one of the few folks who actually chose Speechcraft as a major... You eloquence would be very fitting for that sort of smart, charming character who can 'outtalk' (if theres such a word...) most people and actually make them think you're working for them (ie, be a guild member) and all of a sudden, in an important quest, disappears or changes route.

For the very least, infiltrating a pseudo-guild-member allows you access to restricted areas were u can loot . Always good for chaotic thieves...

I am part of the Thieves Guild. I didn't state it specifically, but I figured it would be pretty obvious. Apparently it wasnt, which is fine.

I'm not Chaotic Neutral as it were. I try to steer clear of D&D alignments, but they are sometimes helpful in description.
Your idea isn't a bad one. Only thing I wouldnt do is rise high in something like the Mages Guild as the story that builds there really wouldnt bother my Thief at all.
Hmmm, in fact I dont think he will join the Mages. He has no magic skill and it wouldnt be realistic for him to join. I know I technically can join, I'm just not sure it makes any sense. Being very friendly with some members though is fine and is probably how I'll play it.

This character does major in speechcraft. I think of this one as being very good at fast talking his way to things, or cutting a deal to get out of things etc. I see him as quite a cunning character.
My previous thieves have been very much of the intelligent, dashing rogue types. Those thieves would be all about flattery, bribery, getting entrance into a high class social event to later fleece the guests of everything of value.

Hmm, I guess my past thieves have definitely followed the line similar to to the Morrowind Bal Molgamer stuff. And like "Gentleman Jim Stacey". That's all very upper class thievery with a higher purpose in mind.
My current thief I want to be really gritty, hands dirty and out for himself above all others. If this were Morrowind, he'd more likely have joined the Camonna Tong (if he was Dark Elf of course). They are much more alike.

God, looking back at Morrowind makes me so nostalgic. There's so much more depth to that game. It's really well thought out and incredibly detailed. I love Oblivion, but Morrowind has some things I dont think Oblivion can beat.

Ah, I love you, you have the right opinions! Morrowind is just so great. :blush:

Anyhoo... In Oblivion there really isn't any guild that offers great quests for "down and dirty" thievery. Thieves Guild is, imho, the suave and prim type. You might have to make up your own quests (if you're into that sort of thing). Depending on what you want your character to do, there'd probably be some possible ideas for those. If he's sort of the Cammona Tong-type, maybe something to do with being a bit of a thug. Maybe your character is completely racist against everything other than Khajiits and steals things from members of other races just to be a nuisance to them, or something. (Sorry, Camonna Tong just automatically makes me think of those meanies in the Balmora Council Club who hated me for being an outlander...)

Well, I was merely suggesting