Depends on how he plays it.
I ran a campaign with a guy who did some pretty not-able-to-type-here stuff, (high priest of Asmodeus), but he had a theme and consistency of behaviour. He wasn't just random jerkface getting away with everything just because.
I did have one of those as well. I tolerated it for a bit, but he pushed it even to the point of suiciding his characters to screw over the party and the plot. Eventually he crossed one last line and he became persona non grata until I was satisfied he cleaned it up (he was coming off of a seriously rough patch in his life). He doesn't even remember most of the stuff he did and when it's pointed out he's admitted that he was ... behaving poorly.
The first character is a lot more likely to squidge on the basis of immorality, but it was the second I banned, because there's a difference between evil and destructive. Evil characters can be amazingly well done. Destructive characters are just obnoxious people there trying to ruin everything, like a spoiled child.
I'm not their parent, they want to act up, they can go home and do that crap.
If however, you want to play a smoother than smooth immoral conman...well don't break any of the basic rules of engagement and we're good. (mainly being; if it starts to look like folks are getting uncomfortable, wrap it up, and next time be a bit less graphic; don't take up all the table time in the session; be constructive to the party)
((that last is merely because PvP is a PitA to mitigate as a DM. I prefer to just leave it in it's closet until it cries itself out and goes back to sleep))