When Flair first joined the Federation it was one of the best times of my life. Then when he teamed with Perfect to me it couldn't have gotten any better! But then it was all down hill from there. I think the guy did a great job but he's not one of the all time greats. The guy never carried the Federation. I continually hear about his days in the other wrestling organizations and how great he was. So if he was that great, was he past his prime once he joined the Federation?
Just because you never followed anything beyond it, the world of pro-wrestling was much bigger than the WWF, and there will always be many fans to whom Flair is and will always be an all-time great. He never carried the Fed because he wasn't there long enough.
Jim Herd was WCW president at the time. He didn't like Flair, who was the WCW "franchise" at the time; he was their booker and main star. Herd was the former CEO of Pizza Hut - no wrestling background. Anyway, Herd fired Flair as booker and replaced him with Ole Anderson.
Business tanked.
Shortly after that, Flair stopped appearing at WCW shows because his contract was up and a new one had not been agreed on. In those days, it was still customary for the champion to place a $25,000 deposit on the title while they held it for "insurance" purposes. Flair's contract expired while he was champ and he never received his deposit. Technically, he was still champion, that belt was his, and that's how it ended up on Vince's TV until the lawyers got involved and the old man had to stop showing it; something about a trademark infringement I think.
If Flair was past his prime at the time, Vince would not have scooped him up so fast. Ric left the Fed once the situation in WCW was ironed out.