I think the only one I'd be worried about fighting would be Lejenda. :I
If that's the case, and if Jay's thinking what I think he's thinking, personally, if I were in Shugo's position, I wouldn't trust the biggest threat to my goals. Shugo seems like the type who, if he were totally aware that you posed a threat to him, and he wanted you gone, and you were presenting yourself to him, he'd have no problem accepting the down payment of the job, and then shanking you.