Man the hypotheticals in this thread would have given that man a much better career.
I never understood why Kona Crush never got an IC run. He never was booked well enough for the main title but he had a decent enough look to support putting it on him, even briefly. This is assuming Bret's not in the picture. I never liked Nation or DOA Crush, not in a "he's a great heel" sense either. Once he got arrested, my stick in the mud self just didn't want him on my TV. Adult me understands people fuck up and deserve second chances, so I guess good on them running with his real life problems in a gimmick (since they acknowledged the arrest on air when it happened).
The NWO stuff was just awkward and awful and I wasn't watching wrestling when he was with Demolition. By the time he formed Kronik I was mostly checked out of WCW programming. So all in all, my vote goes to Kona.
EDIT: his heel turn on Macho *was* done well, I forgot to mention that.