As Dallas Stars GM in 1995, Gainey opted to trade the teams first round pick, Jarome Iginla to Calgary in exchange for Joe Nieuwendyk. That trade it could be argued put the Stars over the top and enabled them to win the cup that season, wth Nieuwendyk the ConnSmythe winner. Niieuwendyk had 6 productive seasons in Dallas, but Iginla has become the more dominant player and is just entering the prime of his career, while Nieuwendyk is all but finished as a player. Gainey has often said that the Stars paid a very high price in that deal. It seems that Gainey's cautious, incrementalist approach occured after that deal, as he has not been one to pull the trigger on big blockbuster deals since. When Gainey came to Montreal his opening press conference stressed the importance from building a team from within, as oppossed to making major deals.
It would have been nice had Gainey signed the likes of Dumont and Carter adding depth to the Habs foward units and then perhaps packaging a young quality player to land a superstar player like a Pronger to put the team over the top. Although the Iginla deal was a decade ago, maybe Gainey does not want a repeat of that situation by trading away a top young player, and the go slow approach is his style as oppossed to the more aggressive role the dice style of a Brian Burke. Gainey's style is pushing the Habs in the right direction, but given the cap constraints and the lowered age level for free agency, will it be quick enough to get the Habs to the cup before the young core of this team is broken up?