Cheap ownership. Remember when the Habs traded away nearly every star the team had after the 1993 Cup win? Traded them all for nothing; it wasn’t for hockey reasons. By the late 90s, the team was barren except for Koivu, basically.
Molson Inc was in dire straits as a business, losing $ and market share, which is why Coors bought them out after threatening a hostile takeover. This is also why they sold the team for little, to get the debt off their books
Combine it with Mtl economy in a tailspin. Even after Gillet bought the team, they were tough times, I was interested in Habs season tix in summer 2002 & got a VIP tour of Bell Centre to pick my choice in the reds, everything was available except center ice section behind team benches