The Penguins were never really horrible with Jagr. It's a fantasy to suggest otherwise. I'm a Pens diehard. Watched them often during this time.
96-97 they still had Mario, Francis, Nedved, Hatcher, Kasper, Barrasso, and finished 2nd in the division
97-98 they lost Mario but still had Francis and most of the other guys listed while adding Straka and Robert Lang and finished 1st in their division
98-99, lost Francis but added Kovalelv, still had Straka, Lang, Hatcher, Barrasso, and made the 2nd round. Still nowhere near horrible.
99-99, still had all the forwards, but their defense was finally looking a bit bleak relative to the better teams in the league at the time. But again, this wasn't a team that was void of talent beyond Jagr.
00-01, Mario returns, forward group is very solid, D looks porous, but they still win 42 games because again, this wasn't a poor team. Behind the top tier franchises? Absolutely but nowhere near a bottom dweller.
Jagr is traded....Lemeiux more or less done after the 03 season.
There is really no reason to suggest Jagr was playing on absolute **** teams in Pittsburgh during the late 90's. It wasn't until 2001-02 that the Pens really started tanking, which is not surprising given their financial troubles and having no real talent outside Straka and Kovalev.
To me, Jagr was an amazing, self serving offensive talent who never really lifted the Penguins in the absence of Mario. He flashed those abilities a few times in the postseason but people talk about Bourque being average or worse than as a postseason performer and at least he led Boston to multiple Cup final berths. The only proponents of Jagr point to about a 5 year offensive peak, but beyond that, there isn't a ton of big moments going on with JJ.
I have no ill will towards him as a Pens fan, I simply think he was a guy who was all about himself, was certainly a brilliant offensive mind, but beyond that, there isn't much that excites me. The postseason is a big black mark on Jagr's career. Players with his talents should have done more. Period.