Mm, definitely some questions here, as others have mentioned.
Beyond those ones, I've a simple one - how in the heck did Jerod find out in the first place that this ring allows him to control wolves? Why would he put it on? What would lead him to suspect that it's enchanted? Is he a wizard in his own right, or as MoonHunter speculated, is it some powerful artifact or bound demon which has possessed Jerod?
Years after this, once Tommy had exacted his revenge on the guildmates who betrayed him to the authorities, he started his own gang of thieves. Contrary to the guild structure that fostered strangers to work together, and sometimes against each other, his gang was family. The Thumbcutters became rather infamous in Farrow and in the surrounding lands. They were indeed thieves of the first rate, but rather than coercion, running rackets and the like, the Thumbcutters were highwaymen and house breakers. They took from the wealthy, from guildsmen and merchants, and their favorite marks, traveling thieves.
The Thumbcutters, however, are still very much part of the community. They give alms at the church, and make an effort at running a front business to look legitimate. They can recognized by their left hands missing the thumb.
This is quite the cute short story, and it has something usable hiddien in it somewhere. The problem is I am not sure where. PCs don't typically have msising thumbs even if they are a guild member and the real interest comes from the perspective of being Tommy Thumb. I suppose he could be a 'friend' of sorts in need of help but that could easily devolve into an irksome quest or one the PCs would not take up at all.