Free agency opens on Friday. NHL general managers will be lining up with their owner’s checkbooks in order to sign the biggest fish on the market.

Colorado Avalanche general manager Joe Sakic, however, expects a quiet day. The team is likely going to be mostly focused on retaining their own restricted free agents, such as Nathan MacKinnon and Tyson Barrie. Sure, there might be some signings, but they are likely going to be minor, and only one- or two-year deals.

A lot of Avalanche fans may be disappointed by this revelation, but they should be relieved. Historically speaking, the Avalanche have really only ever been minor players in the free agent market. When they have tried to make a major splash (i.e. Ryan Smyth, Paul Kariya, Scott Hannan, et. al.), the players have usually failed to live up to expectations.

Some players however, have failed much worse than others. This list is dedicated to those players.

Consider yourselves warned Avalanche fans. This is not a list for the faint of heart. This is a list that is sure to bring up some suppressed, awful memories. These players are the worst of the worst. Without any further ado, here are the five worst free agent signings in Avalanche history.

5. Per Ledin

LedinPosition: LW First signed: 2008-2009 Initial salary: $600,000

Never heard of Ledin? You’re not alone. His Avalanche tenure was short, as he only dressed in three games for the burgundy and blue (going pointless). He spent most of his only season in the Avalanche organization with the AHL’s Lake Erie Monsters. He was signed out of Sweden, where he was a super-pest and strong defensive forward.

Curiously, he was signed to a one-way contract, then never given a real shot in Colorado.  He then lambasted the organization on his way out the door.

Though he is probably the worst of the bunch, Ledin is on this list to illustrate the Avalanche’s ineptitude when it comes to signing free agents from Europe. From Joakim Lindstrom, to Jaroslav Hlinka, to Roman Will and Borna Rendulic, it is simply a market that the Avalanche have never found a way to master.