I am only counting the 21st century because past that it doesn't really matter.
Rask for Raycroft has to be up there. Traded him to a divisional rival, he goes on to break records for that team and beats you in the playoffs 2 times they met (the other time Tim Thomas was in net) all while Raycroft sucked almost immediately and Pogge became a bust.
Rask for Raycroft has to be up there. Traded him to a divisional rival, he goes on to break records for that team and beats you in the playoffs 2 times they met (the other time Tim Thomas was in net) all while Raycroft sucked almost immediately and Pogge became a bust.