But that's just my take.
If you want to engage him in pleasantries, go for it. You don't have to take orders from anybody here either. You don't have much to work with. He hides behind an alias and keeps things on a relatively impersonal footing. The only time he mentioned anything about his personal past was to emphasize what a hard case he was.
I consider that changing his viewpoint is not realistic. Leaving counters to some of the garbage that he spews may be useful, albeit a true pain in the ass.