Montreal Canadiens: Five Worst Free Agent Signings Since 2000

OTTAWA, ON - FEBRUARY 22: Karl Alzner #27 of the Montreal Canadiens looks on during a game against the Ottawa Senators at Canadian Tire Centre on February 22, 2020 in Ottawa, Ontario, Canada. (Photo by Jana Chytilova/Freestyle Photography/Getty Images)
OTTAWA, ON - FEBRUARY 22: Karl Alzner #27 of the Montreal Canadiens looks on during a game against the Ottawa Senators at Canadian Tire Centre on February 22, 2020 in Ottawa, Ontario, Canada. (Photo by Jana Chytilova/Freestyle Photography/Getty Images)
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The Montreal Canadiens have made dozens of free agent signings in the past two decades. These are the five that they would most like to have back.

The Montreal Canadiens have dipped into the free agent pool every summer, just like every team around the league does. They are always sniffing around looking for the right player at the right price to come to Montreal and help the team win games.

Attracting free agents in a city like Montreal comes with some unique scenarios. Some players would love to arrive in town and play in front of a packed Bell Centre in a hockey-mad city every night. Others would prefer the lifestyle in California or Florida a little more where they can be a bit more anonymous when they are running errands.

Looking back over the past 20 years of free agent signings in Montreal, one thing jumps out immediately: they rarely get the big fish that are available. One summer they dipped into the market and came out with Brian Gionta, Mike Cammalleri, Jaroslav Spacek and Hal Gill, but they are usually far more quiet that that.

The Canadiens are constantly in the rumour mill, chasing after the big ticket free agents that are available. However, the tax situation in the province of Quebec is a big deterrent for many players who would rather keep the money they earn instead of handing it over to the government before they ever see it.

Still, over the years the Canadiens have made some great signings. We looked at the top five free agent signings in the past 20 years yesterday. Today, we are going in the other direction. Every team has made some blunders on July 1, and the Canadiens are no exception.

Let’s take a look at the five worst free agent signings that the Montreal Canadiens have made sine the year 2000.