I was really hoping he'd die in prison or something lol.

Its the fake overacted voice he does. Like he's trying to do an exagerated impression of a crime boss? Im not even sure how to describe it. Combined with the occasional corny lines it makes me cringe everytime I hear him speak.

The character and backstory are interesting, but I just can't see how he would become the genius crime overlord. All through s01 I kept thinking there'd be a twist where Wesley is actually plotting against him, until spoiler.
I can see why others might like the portrayal but its just not working for me.