You would be hard-pressed to find a team that has made fewer trade deadline deals over the past five years than the Montreal Canadiens. In total they’ve made just four in the final day of trading, as the club has tried to stay away from making any rash decisions.
2010 Trade Deadline
Although the Canadiens were silent on deadline day, they did send forward Matt D`Agostini to the St. Louis Blues for Aaron Palushaj the day before the deadline. Palushaj never found success in Montreal, playing in only 41 games, before being picked off waivers by the Colorado Avalanche during the shortened 2012-13 season.
2011 Trade Deadline
G Drew MacIntyre 
D Brett Festerling
The Canadiens made one deal at the 2011 trade deadline, and it was of little consequence. The Habs acquired netminder Drew MacIntyre from the Atlanta Thrashers (now Jets) in exchange for defenceman Brett Festerling. Both MacIntyre and Festerling never even played a game with Montreal.
In the week leading up to the deadline however, the Canadiens did acquire forward Nigel Dawes and defencemen Brent Sopel and Paul Mara in two separate deals for a pair of draft picks and a prospect. The newly minted Canadiens combined for 36 games with no goals and four assists in their time in Montreal with Mara racking up the bulk of the action.
2012 Trade Deadline
2013 2nd rd pick, Conditional 2013 5th rd pick 
F Andrei Kostitsyn
The 2012 trade deadline saw the Canadiens finally rid themselves of forward Andrei Kostitsyn. The skilled Belarusian had developed a bad reputation for being complacent, and lazy on the team. Adding to the mess was the relationship his brother, Sergei Kostitsyn, had with the franchise that soured his name as well. In exchange the Habs received a second round pick that turned into Jacob de la Rose who just made his NHL debut at the age of 19 in early February.
Montreal, who went on to finish last in the division and miss the playoffs, also did some roster unloading by sending Hal Gill to the Nashville Predators 10 days prior to the deadline.
2013 Trade Deadline
Once again the Canadiens went radio silent at the trade deadline. Their only move came the day before when the acquire prospect defenceman Davis Drewiske from the Los Angeles Kings for a fifth round pick in 2013.
Although Drewiske is still in the Canadiens’ system, the real notable trades came in the months leading up to the draft where they acquired current backup goaltender Dustin Tokarski, and forward Michael Ryder. At the same time they sent Eric Cole to the Dallas Stars after an extremely slow start to the season.
2014 Trade Deadline
F Thomas Vanek, 2014 conditional 5th rd pick
F Sebastien Collberg, 2014 conditional 2nd rd pick
G Devan Dubnyk Future considerations
With the Canadiens in the process of securing a playoff spot, Montreal made two moves on deadline day with the biggest being the acquisition of forward Thomas Vanek from the New York Islanders. Vanek went on to put up six goals and 15 points in the 18-game stretch run to the playoffs, and even chipped in 10 points in the post-season helping lead the Canadiens to the Eastern Conference final.
Vanek was always going to be a rental player, so losing him after the club’s playoff run for prospect Sebastien Collberg, and a second round pick wasn’t a total loss.
The Canadiens also acquired Devan Dubnyk from the Nashville Predators for essentially nothing, and acquired defenceman Mike Weaver from the Panthers. Weaver suited up for all 17 playoff games for the Habs, while Dubnyk only played for Montreal’s AHL affiliate.
