The Conn Smythe is hard to give to a player from the losing team. However, It has and should still happen. Since the award has been given out, 5 of 42 times the award when to a player from the losing team. 4 of those times it was the opposing goalie. Here is the list.
65/66 - Roger Crozier 67/68 - Glen Hall 75/76 - Reggie Leach (the only non-goalie) 86/87 - Ron Hextall 02/03 - J.S. Giguere
The Conn Smythe is for the most valuable player in the playoffs. If the most valuable player is on the losing team he should win it. I mean most times the team who wins the Stanley Cup they actually have a team with some great players but none of them are so valuable, they all work together. If they would give it to the most valuable player in last years playoffs Roberto Luongo could have won it I mean he took that team way father then they should have. Most times it goes to the Stanley Cup winner. Last year it went to S.Niedermayer and I won't deny that he played well but I really think that Alfredsson carried that Senators team.