jimmy showed he was smart way back in the day when he started directing the videos and getting involved in all that shyt for a check. that's pure hustler mentality.
the things that always stopped me fully embracing him was:
1) terrible on he mic (this has been partially mitigated by good production, a&r work, and some improvement... but he did used to be terrible a fukk)
2) he always came across musty as fukk. despite obviously being rich, he looked like he woke up in a dumpster truck
and probably more significantly, in recent times, dude is almost certainly a snitch
but props to him for making a success of himself, much respect for that