NHL Trade Deadline: Ranking every team’s worst ever trade

SACRAMENTO, CA - APRIL 3: Wayne Gretzky of the Los Angeles Kings in action against the Edmonton Oilers at the Arco Arena on April 3, 1994 in Sacramento, California. The Kings defeated the Oilers 6-1. (Photo by Rocky Widner/Getty Images)
SACRAMENTO, CA - APRIL 3: Wayne Gretzky of the Los Angeles Kings in action against the Edmonton Oilers at the Arco Arena on April 3, 1994 in Sacramento, California. The Kings defeated the Oilers 6-1. (Photo by Rocky Widner/Getty Images) /
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SUNRISE, FL – JUNE 26: General Manager Dale Tallon of the Florida Panthers talks on the phone at the draft table during Round One of the 2015 NHL Draft at BB
SUNRISE, FL – JUNE 26: General Manager Dale Tallon of the Florida Panthers talks on the phone at the draft table during Round One of the 2015 NHL Draft at BB /

With the NHL trade deadline upon us, we count down the biggest mistakes that every team has made.

It’s not something to be proud of, but even the best general managers have made a mistake at one point. Sometimes, it’s hard to blame them. Nobody can predict the future and know how someone will turn out, or maybe that player just didn’t work in the coach’s system. However, with the NHL trade deadline upon us, now is as good a time as ever to revisit some of those past blunders that range from simple mistake to boneheaded.

In principle, a trade is supposed to be a deal that fits both teams’ needs. If a bottom-feeding team needs a draft pick or a prospect, they can deal away a player that may experience a resurgence on a playoff team. And while most of these deals do that, the reason it failed is because one team ended up striking out on a player that they thought had lots of potential. In other cases, a player got dealt because he was unsettled and ended up reaping the rewards for the other team.

Trades have changed over the years, mainly due to the salary cap. Teams can no longer deal cash to each other like they used to, so trading a player with a large contract will often mean including a player with an equally bad contract or retaining salary. In other words, it may look bad in the short term, but it gets better in the long term. We saw the Toronto Maple Leafs do that when they took back Milan Michalek and Jared Cowen’s contracts so that they wouldn’t have to retain Dion Phaneuf’s salary. They also cleverly manipulated the cap in dealing David Clarkson for Nathan Horton who they would later put on LTIR.

I only chose one trade per team so, for example, I couldn’t include both the Wayne Gretzky and Mark Messier deals. Some teams got over these deals relatively quickly, while for other teams it still hurts them to this day. Whatever the motivation behind these deals were, what they all have in common is that one team lived to regret it.

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