Well I have an idea, but my memory on Oblivion is starting to get fuzzy as I haven't played in a while and I'm not completely sure if this will work. But it's definitely worth exploring.
I believe you can artificially advance the Thieves Guild questline without actually doing it by taking the Boots of Springheel Jak From Jakben Imbel's corpse at any point during the game. Then you will be able to meet up with the Gray Fox (I think) at which point you should be able to reverse pickpocket items onto him, causing him to unequip what he's wearing and equip what you gave him. Then you can pickpocket those items from him. --- A new study shows that by 2025, American children will be too obese to ride hover boards.
You can't pickpocket him. He always turns around and says "Why you dirty thief! How dare you try to steal from me!" or something along those lines. --- "Your reality, sir, is lies and balderdash, and I'm delighted to say that I have no grasp of it whatsoever!" - Baron von Munchausen
Having those boots early doesn't work. The Gray fox only appears at certain locations that are triggered through the theives quests. You also can't pickpocket anything off of him, even with 100% Chameleon.
Also, TC why would you want his gear if you don't like sneaking?
So you can get the Gray Cowl of Nocturnal earlier than you're supposed to be able to. However, you cannot get it without starting the Thieves Guild questline. You have to get up to the point where you meet the Gray Fox for the first time, and at that point you will be able to obtain the Cowl.
--- A new study shows that by 2025, American children will be too obese to ride hover boards.
PadreV is right. once you complete the theives guild quests he becomes non-essential. i took him out when i went on a rampage LOL. --- Dr. Hibbert: Homer, do you see anyone in the room that isn't real? Homer: Just you, Marge and Yogi Bear.
although i wouldn't save after taking out the gray fox...even after the theives quests are over. --- Dr. Hibbert: Homer, do you see anyone in the room that isn't real? Homer: Just you, Marge and Yogi Bear.