While a member of the WCW there were a number of opportunities for him to fulfill his untapped potential & become a top star in the wrestling business. Though Brian at this time was still on the younger side he was slowly bringing together all of his skills including incredible in ring skills and among the best on the microphone. According to the WCW Timeline: 1990 featuring Jim Cornette who spoke about Pillman and the planned push that was scrapped in 1990 following Sting's debilitating injury. After watching the DVD I firmly believe that if the angle would've have gone off the right way then Pillman would've likely become the World Champion & maybe that would've been enough to keep Flair in the WCW.
Before you think I am going to skip over his run in 1996 before heading to the WWF don't get me wrong it was a great run, but their was no way Pillman would've been World Champion. I am aware that it was around this time when Brian had the tragic motorcycle crash, but also not long before that he was the most intriguing talent in the business after the "I respect you booker man" stunt. However, due the shortsighted nature of that angle and Bischoff not working out Pillman's return before he left the legs were cut off the angle soon after it got going.
Either way though it is hard to say that Brian Pillman at one point or another wouldn't have or couldn't have been in the Main Event of WCW or WWF at a time. I will go out on a limb and say that had Brian not had the terrible accident I think he would've have finally had his feud with Steve Austin for the WWF Title. There is no doubt in my mind that Brian as the Loose Cannon in Attitude Era WWF would've have worked and done extremely well. But WCW coming to the realization of the talent they had and his arrival in the WWF was just a little "Too Little Too Late."