Let's look at those rosters.
1989 Jazz:
PG: All-Star, 2nd-team All-NBA, 2nd-team All-Defensive, 7th in MVP vote, HOF and one of the greatest point guards ever
SG: former ROY and regular 20ppg scorer who was past his prime but still putting up 13ppg
SF: putting up nearly 20ppg
PF: All-Star, 1st-team All-NBA, 3rd in MVP vote, HOF and one of the greatest power forwards ever
C: All-Star, 1st-team All-Defensive, Defensive Player of the Year, 13th in MVP vote
1992 Jazz:
PG: All-Star, 2nd-team All-NBA, 2nd-team All-Defensive, 12th in MVP vote, HOF and one of the greatest point guards ever
SG: former All-Star still in his prime averaging 20+ ppg
SF: mid role player
PF: All-Star, 1st-team All-NBA, 4th in MVP vote, HOF, and one of the greatest power forwards ever
C: Former All-Star and DPOY, pretty washed but still averaging 2.5 blocks/game
1995 Jazz:
PG: All-Star, 1st-team All-NBA, 2nd-team All-Defensive, 8th in MVP vote, HOF and one of the greatest point guards ever
SG: former All-Star and 20ppg scorer, still in his prime averaging 17ppg
SF: shytty role player
PF: All-Star, 1st-team All-NBA, 3rd in MVP vote, HOF and one of the greatest power forwards ever
C: platoon between washed former All-Star and washed former 20ppg player
That's what sort of rosters they were fielding when they were struggling. Every fukking year they had 2 of the best players in the game, a 3rd player who was at a borderline all-star level, and a former all-star who was now a crafty vet.
At the time, Malone was considered the greatest PF ever and Stockton was considered a top-3 point guard of all time. If that was true, and they were both in their prime, with a good coach, together with all that continuity, and having multiple other solid players on the squad, how is that not enough to do something?
Yet in the 10-year stretch from 1986 to 1995, they lost in the 1st round 6 times, in the WCSF twice, and in the WCF twice. Only once did they reach a Game 7.
How is that possible?
Their 1997-1998 rosters were actually sad compared to what they were fielding 1988-1995. Stockton and Hornacek were too washed to be the starting backcourt for a title team and their SF and center rotations were less than mediocre. They only advanced those years because literally everyone else had aged out.