Let's be honest, being the GM of the NHL's most storied franchise during the most monumental season the team has ever prepared must give Bob Gainey fits. The pressure to be a part of this team as management or as a player in a "normal" year is enough to make people fizzle. (see Michael Ryder a la last year) In saying this, The pressure of performing in a hockey hotbed such as Montreal, Toronto, New York is not for the weak of heart, which is why softies like Bryan McCabe retreat to places such as Florida where they can collect paychecks out of the spotlight.
The General Manager (and the coach) ultimately take the most heat if the team doesn't perform and with the way Gainey has been criticized by fans and media alike for apparently doing nothing to improve this team (failed signings such as Briere, Lecavalier, and now Sundin) this really is a year in which they MUST win the Stanley Cup.
It's just too perfect of a story for the Canadiens. With the Centennial year falling on this season, in which the team is hosting the All-Star game as well as the NHL draft, the Canadiens will be trying to win the Cup in order to keep the streak of winning atleast one Cup per decade.
I for one, believe that Bob Gainey's patience and presence of mind to keep the core of this team together and really make informed decisions regarding his roster will pay off when the Canadiens win Lord Stanley's mug this year. Criticize the man all you want for not bringing in a big-name (Sundin) to help the team. With all the distractions the team will have to deal with, adding the former captain of your bitter rivals would just add more. Gainey's additions were all solid, and with the team gaining valuable experience from last year, I truly believe that they have what it takes to go all the way.