When he knew WCW was sinking:
As I've said, it became apparent to me around August of 1998 that as a result of the Time Warner merger and a lot of corporate restructuring (and politics) that it became pretty obvious to me that WCW was in for a long hard ride.
If he regrets not pushing cruiserweights more:
I don't regret anything because I've said in my 83 weeks podcast, context is really king. In terms of context, the Cruiserweight division was a very important part of Nitro's success. That, combined with the fact that we had a very dense main event roster (Savage, Hogan, Piper, Sting, Luger, Goldberg, DDP, to name a few) that there's only so much room at the very top. With context of the time, I don't regret pushing some of that well-established talent off to the side to try to make room for a lesser known, though incredibly talented roster, but any objective person would most likely agree that the only reason why Jericho/Eddie/Benoit were able to get over the way they did was because of the massive amount of prime time exposure that I gave them in WCW.
But I wouldn't have been able to achieve that same thing during the late '90s with the Cruiserweight division because I had too many bigger stars in main event positions.