Well...
It starts with Stephane Richer. Richer had an awful 95-96 season with the Devils, after leading the said Devils in Regular season and Playoffs scoring for their '95 Cup run. We know today that Richer suffered depression and that he was about to attempt suicide right after the '95 Cup Run. Richer had a somewhat better 96-97 season, but was by then 30 years old.
Traded by the
New Jersey Devils to the
Montreal Canadiens for
Lyle Odelein.
I'm on the fence as to whether this was, in and of itself, a good trade. The Canadiens probably needed Richer and the 96-97 version of Richer could've remained a Hab for a few seasons. Odelein did end up having the longer career, being a super reliable #4 D-Men on a great team, but it's worth noting that his PIMs went way down with the Devils; it's almost like he could focus on his play when he wasn't a main enforcer. The trade made sense in a way, it just didn't play very well for reasons we know today.
Then, Richer...
Traded by the
Montreal Canadiens with
Darcy Tucker and
David Wilkie to the
Tampa Bay Lightning for
Patrick Poulin,
Igor Ulanov and
Mick Vukota.
Tucker was underwhelming and annoying as a Hab, but didn't yet blossom. Wilkie wasn't yet a bust - but was nearing that territory - and would end up a bust. Poulin and Ulanov were regular players but ultimately depth parts, but Poulin seemed to be miscast everywhere in the lineup (very bad defensively, not skilled enough for Top-6 duties but nonetheless skilled enough for Top-9 duties, big body but no really a power forward, and also an early bloomer, so he was a bit past his prime at 25). Ulanov was a bruiser who could hit like a serious truck but wasn't great at anything else, but could play a very simple defensive game. I still don't understand how he could be a Top-4 D on a pretty good team (the 00-01 Oilers). Then, Ulanov...
Traded by the
Montreal Canadiens with
Alain Nasreddine to the
Edmonton Oilers for
Matthieu Descoteaux and
Christian Laflamme.
So, in terms of assets we went from Odelein, Tucker, Brad Brown (the logical counterpart to Nasreddine) and Wilkie to Christian Laflamme, a post-prime Poulin, Matthieu Descoteaux (a first rounder acquired at D+4 who was really suspect when we traded for him) and the corpse of Mick Vukota. By the end of 00-01, all that remained of this is 28 games of Patrick Poulin on the 4th line, which is a worthless asset. Meanwhile, the likes of Tucker and Odelein still had value, and we lost value on Ulanov.