In my opinion the Gray Fox character has potential but he has not been used well in Oblivion.

I always wondered how he would be in the guild of assassins and Skyrim skyrim could be the perfect stage for a change of team.
Here's how the character may appear in the darker world of skyrim (open the img to full size to see it better).

http://img28.imageshack.us/i/foxne.jpg/

Uploaded with http://imageshack.us

If the Mask wearer is in the Brotherhood why not, otherwise not really.

I don't see why the gray fox character wouldn't live on. The cowl can still be worn by anyone unless it was destroyed look below . There place would permanently be known as the grey fox, which is why everyone thought he was immortal.

We will probably see the gray cowl in one shape or form. If not on a character, it might have been returned to Nocturnal.

Thieves Guild doens't murder, they steal. So this is kinda useless. The character design isn't interesting as an assassin.

I really don't see the point in this. It's like making a thread saying "What if Hannibal Traven, Arch-Mage of the Arcane University, was in the fighters guild instead!"

I wouldn't be suprised if the grey fox was killed off and forgotten but therez a reference of a legendary thief called the red couger or something

But the Gray fox could be anyone hidden underneath the mask. Technically they are no one since they are wearing it, but you get the point.

Huh? The Gray Fox is a thief, not an assassin, it would really tarnish the name of the Gray Fox to completely turn around the ideals of the Cyrodilic thieves guild like that.

And that brings up an important point: The Gray Fox is part of the Thieves Guild in Cyrodiil, not in Skyrim.

Really? I didn't know this.. I thought the Gray fox was the leader of all the thieves guild.

http://uesp.net/wiki/Oblivion:Gray_Fox

It never says he only rules over the Cyrodiilic Thieves guild, it actually says "the mysterious leader of one of the most secretive organizations in Tamriel, the Thieves Guild"

So why couldn't he/she/the gray cowl appear in Skyrim?

The grey cowl could perhaps be a reward for Nocturnal's daedric shrine quest.

no Gray fox for Dark Brotherhood because he needs to stay with the Thieves he is not an Assasin but a Thief

Maybe Another Masked Guy in Dark Brotherhood

I agree, the gray fox is the face of the thieves guild. The DB has a face, Sithis.

Why would the Grey Fox, leader of the Thieves Guild (which doesn't murder at all), randomly decide to switch to the Dark Brotherhood (which murders basically as much as possible)?

Also I wouldn't think the Gray Fox's massive bounty, outlaw status, or legendary fame would be something an assassin would find very useful. So, no. The Gray Fox/Cowl should at least stay with the Thieves Guild, if not exclusively with the Cyrodil group. Unless of course it has been returned to Nocturnal, in which case it could be a reward for his quest.

The Gray Fox was never mentioned in Daggerfall or Morrowind. I'm pretty sure every province has their own separate Thieves Guild and none of them interact with each other or follow the same rules.

I agree that those who wear the cowl is usually belonging to the Thieves' Guild,

But imagine that one of the future owners of the cowl using it in different and bloodiest ways ruining the name of Gray Fox as we know it...

There are many ways to tell a story, and in skyrim we will see drastic political and social changes

Interesting? Yes, but I prefer that he stay a member of the TG. But since the spell on the Cowl was broken in Oblivion it is no longer officially bound to a single person. Odds are that the owner of the cowl would have handed it off to the best TG member when he was getting on in years. The way I have always played TES games is as a person who can only be in one guild. I like to believe all the different guilds are being done at the same time, but by different people.

The Gray Fox was never even mentioned in Morrowinds thief questline, so I very much doubt that he's the leader of all tamriels thieves guilds.

then he would be the dark gray fox

Then I wouldn't like him nearly as much. I really disliked OB's Dark Brotherhood in terms of aesthetics. They just tried too hard to evil and intimidating and just reeked of absurd, cartoonish misanthropy; I loved the Gray Fox and the Thieves' Guild however. They had an awesome social justice dimension running in tandem to their business-goals and just seemed like an all around awesome bunch of folks - I imagine them in their off time breaking out an accordion, a lute, and some jug wine and telling tales of Hrormir by torch-light down on the waterfront; whereas I can picture the Dark Brotherhood ritualistically cutting themselves in a coffin before an audience of their peers.

Agreed, except on the music genres. DB would be just Emo, and TG would be the AC: Brotherhood soundtrack. I hope they are more like the Morag Tong this time. Cool, calm, and professional.

Let some other guy with a mask be in charge of the Dark Brotherhood in Skyrim... He could have a mystical black skull mask that was blessed by Sithis and can make the wearer cloaked
(Maybe a Batman reference?)

No GF in Skyrim...he was only associated with the Cyrodiil TG.