Sure, Calder Trophy winner means something. It means he had a great rookie year. Everybody's saying Raycroft has only had one bad year, but he's only had one GOOD year too.
The Leafs D isn't exactly their strong point and I don't put much stock into them playing well for one goalie rather than another. It really was the team full of young pluggers that hustled and played hard for 60 minutes that won them the string of games down the stretch, not necessarily great goaltending.
Remember, Jim Carey won the Vezina... Where is he now?
Obviously, no one knows just how good Rask is going to be at the NHL level, same with Pogge, but it's still up in the air if Raycroft can get back to the level he was at in 03-04 as well.
Based on what I know, Rask is highly regarded by several resources and has been for a long time. Pogge came out of nowhere and had one good tournament, but I'd be very wary of basing a potential NHL scouting report on one tournament. Raycroft was hurt for a bit, true, but he did get 30 games last season. That's a decent share for a guy who was hurt. Only problem is, he only won 8 of them. It's not like Raycroft played well when healthy last year and he ultimately lost the starter's job by being out-played rather than just being injured. Raycroft was healthy when Tim Thomas was decided on as the starter when Toivonen went down. He's been blasted for being ineffective with the new rules on padding and was only expendable because an injured Hannu Toivonen and AHL veteran Tim Thomas were deemed more valuable.
Bottom line, it'll probably be years before we know the true winner and loser of this trade. All we have now is opinions and my opinion is that the Leafs overpaid. They overpaid for Kaberle and they'll likely overpay for McCabe. Leaf fans are used to it after years of overpaying for tickets.