In 2008, Gainey had that chance with Hossa and wouldn't pull the trigger. Maybe if we get Hossa we finish off the Bs in 5 and don't have to play 7 games, and maybe we get past Philly as a better, rested team. Its all guesswork, but picking up Vanek is a huge move and I'm not sure Gainey would have had the willingness to pull it off.
If I recall, it was Atlanta who chose instead to take the Pittsburgh package, which in hindsight was inferior. Also, that Hossa deal would have included Hedberg to back up Price. It was the reason he traded Huet for a second because the second was to be flipped in the Hossa deal.
It was reported back then that the Habs offered Lapierre, Higgins, Grabovski and a 2nd for Hedberg and Hossa. Waddell chose Christiansen, Armstrong and Esposito (who was the deal breaker)