Question: has anyone ever won the conn smythe on the losing team

Answer: Yes, Though the award rewards a player who performed particularly well over the entirety of the playoffs, it has never been given to a player whose team did not at least reach the Stanley Cup Finals. The trophy has been awarded to members of the team that lost the Finals five times, most recently Jean-Sebastien Giguere of the Mighty Ducks of Anaheim in 2003, who backstopped his team's surprise run to the Finals, where they pushed the New Jersey Devils to seven games. The only skater to win the award in a losing cause is Philadelphia's Reggie Leach, who won it in 1976 as he had set a league record for most goals in the playoffs (19), which included a five-goal game in the semifinals and four goals in the Finals, even though the Canadiens swept his Flyers.