Five Worst Montreal Canadiens Trade Deadline Deals Ever

The Montreal Canadiens are down to the last couple of days before the National Hockey League trade deadline arrives. They are sitting near the bottom of the NHL standings and will surely be looking to sell this week.

That process has already begun as Sean Monahan was sent to the Winnipeg Jets for a first round pick in 2024. There is also a conditional third round pick heading to Montreal in that deal but it only gets transferred if the Jets win the Stanley Cup this season.

Monahan is doing his part to make that happen, as he has scored eight goals in his first 12 games with the Jets and has solidifed their center ice position. They do have a great team and have surged to the top of the Central Division standings so who knows, perhaps that extra pick will end up in the Canadiens hands soon.

What other picks could the Canadiens acquire? They don't have a list of pending free agents that are sure to move, as Tanner Pearson is the only pending unrestricted free agent on the roster. He isn't having a fantastic season, with 11 points in 42 games but is a trusted veteran with Stanley Cup winning experience so he could be on the move.

Even if the Canadiens can land a late round draft pick, they may as well pull off the trade. Adding as many picks at this time of year could lead to a huge payoff down the road, and if the player you are shipping out has his days numbered with your organization you may as well get something for them.

We have seen some of these types of deals work out really well for the Canadiens over the years. Unfortunately, some trade deadline deals have not. Here are the Canadiens five worst trade deadline deals ever.