It certainly would have been interesting. People forget that even with Jordan on hiatus for two years, the Bulls still won 55+ games with Pippen and had deep playoff runs.
While Pippen couldn't have done that with the Celtic team he was going to, it wouldn't be a stretch to think he could have done it had Pitino found a way to get another star next to him, even if that star wasn't on Jordan's level.
to me, that speaks volumes about the low-quality of basketball at that time rather than anything great about Pippen. I know that's not a popular opinion but that's how I recall those days in the league.
I think you probably need to look at the league during those years again. There were quite a few very good teams. Magic, Knicks, and Hawks were all very solid teams in the East. Pacers, Nets, and Heat were on the rise. Cavs were still pretty solid. Out west the Rockets, Sonics, Suns, and Jazz were all excellent teams. Spurs, Warriors and Blazers were pretty darn good. Now granted none of those teams would go down as all time great teams, but the league on the whole was pretty strong in 93/94 and 94/95.
no need to look back. many decent teams that had a couple of star players and a lot of middling role players. no teams that would have been a title threat in the 80's or 2000's.
probably one of the reasons I discount the 'greatness' label bestowed on Jordan's title teams. I don't those teams would have won a title in the 80's either. those 80's teams (C's, Lakers, Sixers first half of decade, even Pistons at the end of the decade though I hated their style of winning) I use as a standard for greatness.
a Houston team led by a 2nd year Hakeem was in the Finals in the 80's. Seattle was a pretty darn good team led by Payton and Kemp, but that also had Schrempf, Perkins, Gill, and McMillan. The Jazz of course had Malone and Stockton, but also had Russell, Hornacek, Chambers, other Malone, etc. Knicks were pretty good with Ewing, Oakley, Starks, Mason, Anthony, etc. Magic with Shaq, Penny, Anderson, Scott, Skiles, etc. were pretty good (frankly that Magic is pretty darn close to Shaq's title winning LA teams). Pacers had no superstars (though Miller was darn good), but went about 9 deep with guys like Antonio Davis, Byron Scott, and Sam Mitchell coming off the bench.
I think Jordan's dominance has significantly skewed what people felt of the other teams during the 90's. There were a lot of really strong teams, the Bulls were just so good it overshadowed everyone else.