Ed Belfour in San Jose.
Numerous contract disputes among star players (and Eddie's inability to get along with his backup goalies, like Hackett and Hasek) led the Blackhawks from dissembling their nearly-great team and shipping the Eagle off to San Jose for three players and a pick. Expectations were high for Belfour, who already had a Calder, Vezina, and was a finalist for the Hart a few years prior, but Eddie simply could not live up to expectations and was run out of town during the summer when he signed with Dallas. This is the biggest black mark in the Hall of Fame goalie's career, at least as far as on-ice performance is considered.
Jonas Gustavsson in Toronto.
In hindsight, it's pretty clear "The Monster" - who is just about average size for a goalie these days - was little more than fool's gold prior to his acquisition by the Leafs. Noted showman and occasional general manager Brian Burke worked hard to make the media and fans optimistic about Gustavsson, who never found his game in the NHL and was relegated to backup/platoon status for the majority of his career. Although he was able to steal the starting job from Toskala, which is about as easy as stealing a first-round pick from the Coyotes, he was just another horse on the Leaf-goalie carousel before losing his job to James Reimer.