By the time the Attitude Era/MNW got rolling, managers in both the WWE and WCW were being phased out or pushed down the card. But do you think there are any managers in their prime that would have done well during this period? I think Sensational Sherri causing trouble for both Sable and Sunny would have been fun.
Sherri already was in WCW around that time, though. And she was banged up and wanted out of the business. And managers were totally running around all over the place! Jim Cornette, James Mitchell, Paul Bearer, and Sunny, just to name a few!