Five Worst Montreal Canadiens Trade Deadline Deals Ever

The Vincent Damphousse Trade

The 1998-99 season was one to forget for fans of the Montreal Canadiens. The Stanley Cup winning roster of six years earlier was being picked apart and the team could not look further from contending for another one.

Though they did a pretty good job keeping pucks out of their net, they were among the lowest scoring teams in the league. So, as the trade deadline approached, they decided to sell, sell, sell.

One player they chose to move out was captain, Quebec native, and player that wanted to stick around Montreal for a very long time, Vincent Damphousse. He was not having his best season, but no one around him could score, and Damphousse was 31 years old. So they traded him to the San Jose Sharks while the team was on a plane heading home from their game in San Jose against the Sharks.

The trade initially seemed like a decent one for the Canadiens, as they received first and second round picks for what appeared to be a declining asset. The problem was, Damphousse could still score, he just needed better wingers than Benoit Brunet and Turner Stevenson to make it happen.

He finished that season with 13 points in 12 games for the Sharks and then had 70 points the following season. Injuries slowed him in 2000-01 but he had 46 points in 45 games played. He reamined healthy in his final three seasons, scoring 58 and 61 points and then adding 14 points in 17 playoff games in 2004, his final year in the NHL.

Meanwhile, the Canadiens drafted Marcel Hossa and Kiel McLeod with those two prominent picks. The management team at that time didn't have the self awareness to know they couldn't draft, making trading for draft picks essentially useless.