Many things.
Alcoholic for one.
Being a trust fund kid certainly didn't help build character or anything, given he refuses to take responsibility for what he says (Montagraph lawsuit) or does (Attend swingers parties).
Being an open degenerate is also something to take into account. When you're protecting a pedo (Vito), a retarded nigger creep (Drexel) and sexpats (that retard living in Korea) it truly helps paint an excellent portrait of who you are.
And I'm not that deep into the Rekietaverse, only recently catching up to it because the Drexcel drama is too enjoyable to ignore.