Solid question; about two of the greatest teams of All-Time. It would obviously be a 7 game series. In my mind, I'd choose the more complete team, and that was the 1986 Celtics. While Basketball was extremely competitive in the 90s, it was off the charts better in the 80s at the time of this Celtics team which had 5 Hall Of Famers (Bird, McHale, Parish, Dennis Johnson and Bill Walton off the bench), but that Bulls team was ranked 1st in Offensive Rating and 1st in Defensive Rating on their way to a 72 win season. The Celtics were no slouches either; this would be the third title in the 80s they'd win, with a 3rd in Offensive Rating, and 1st in Defensive Rating in the better era of basketball.
Some incredible matchups here; (Note: Dennis Johnson was the Celtics PG; but as he was their best guard defender, he'll be handling duties of Michael Jordan.)
PG -- Danny Ainge vs Ron Harper; Ainge was the better offensive player here, one of five C's who averaged in double figures, but Harper was a fantastic perimeter defender. However; Ainge was as well, even with Harper at the time's limited offensive game. Edge: Danny Ainge
SG -- Michael Jordan vs Dennis Johnson -- In our first Hall of Fame battle, the vastly underrated Dennis Johnson, who did a very good job at containing Magic Johnson in their Finals win in 83-84 would be atleast a 'challenge' to Michael here. Dennis was quite the pest with his long reach, and his ability to get in to the passing lanes. That said, I don't believe he'd be able to stop Michael of course; so the edge to Jordan. Edge: Michael Jordan
SF -- Larry Bird vs Scottie Pippen -- In the series best matchup; Bird vs Pippen would be a fun battle to watch. Bird's creativity versus Pippen's athleticism on full display. Pippen was an elite defender; but Bird in 86 was still in his prime as the top player in the league, who could do it all from pass, score and rebound. Pippen in 96 was no different, the prime of his career. This one is a wash. Edge: Even
PF -- Dennis Rodman vs Kevin McHale -- In another fun matchup here of two post beasts, we've got the Power Forward with the greatest footwork ever in McHale, and the best rebounder and possibly defender in the post ever. This would be a crucial matchup in the series. If McHale, who had a knack for getting in players heads was able to get into the volitale mind of the Worm; there could be foul issues for Rodman. Rodman would limit McHale's points, but Kevin was an excellent passer. Still this is probably a wash. Edge: Even.
C -- Robert Parish vs Luc Longley -- While Longley was 'decent', he was seldom used for anything other then grabbing boards, or setting high picks on the perimeter. Parish ran the floor like a cheetah, played intense defense in the post, and occasionally if needed could get it done with scoring. Parish is the easy call, and could prove big in the series, with the Trio of Bird, McHale, and Parish taking the C's game into the post, where the Bulls even with Rodman were smaller then the Celtics. Edge: Robert Parish
Bench: As far as 'depth' I like the Celtics here. While the Bulls did have Kukoc and Kerr off the bench, it realy ends there in terms of solid contributors. Bill Walton (who won 6th man of the year) Cedric Maxwell, Quinn Buckner, etc
Coach: I give the edge to Phil Jackson; though KC Jones, who played on those 60s Celtics teams was no slouch of a coach.
I like the Celtics in 7; they had 4 guys who averaged over 7 rebounds per game, and their overall size and the ability to play different styles of play; whether it was running the floor, the half-court set or in the post, gives them a slight edge over the Bulls here. This is my dream-series if I could choose one. (Though I might have selected the 83-84 Celtics; but both Celtics teams were amazing)
People might not agree; but the competition was better in the 80s; and this Celtics team like the others before it in the 80s were dominant.