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Photo Credit: Sergei Belski/USA Today Sports

What’s the worst trade in Calgary Flames history?

Dating back to grade school, virtually everybody is familiar with trades. Back then, trades are used to optimize your lunch-time preferences – when your parents send you to school with a pudding cup, you try to wheel and deal to upgrade it to a Fruit by the Foot. A good trade is one that gives both sides what they want. A bad trade is one that sees items of unequal value swapped and leaves one side with carrot sticks and the other with pizza Lunchables – something that makes you wonder what they were even thinking.

Last week was the 30th anniversary of the Doug Gilmour trade, one of the worst trades in Calgary Flames history in terms of unequal value. But is it the worst trade in franchise history?

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The Gilmour trade was originally fairly simple and became much more complex and unwieldy. Gilmour was in the middle of a contract dispute with Flames general manager Doug Risebrough – this was the beginning of a period where the Flames would begin to get clobbered financially by the crashing Canadian dollar and would be forced by economic pressures to sell off good players for pennies on the dollar.

Dealing with his former boss Cliff Fletcher – formerly Flames GM when Risebrough was assistant GM and then GM of the Toronto Maple Leafs – the swap swelled to a 10-player trade. Headed to Toronto were four members of the 1989 Stanley Cup championship team (Gilmour, blueliners Ric Nattress and Jamie Macoun and backup goalie Rick Wamsley) and top prospect Kent Manderville, in exchange for forwards Gary Leeman and Craig Berube, defensemen Alex Godynyuk and Michel Petit, and goalie Jeff Reese.

Economically, the trade made sense: the Flames opened up payroll room at a time where that was a big benefit for them. On the ice, the trade made the Flames worse. Moreover, they added assets that were very, very difficult to flip for further assets. The five players they acquired were turned into Brian Skrudland (as a trade deadline rental), Dan Keczmer and a fifth-rounder.

There are a handful of trades that involved similarly iffy value. One that we’re not including is the Jarome Iginla trade to Pittsburgh – he was swapped for a first-round pick and college forwards Ben Hanowski and Ken Agostino – because Iginla’s no-move clause basically negated the club’s ability to really shop him around and maximize his value. (We’re also not dinging deals that were overpays – we’re looking at you, Travis Hamonic for a first-rounder and two second-rounders – if the logic behind the trade seemed fundamentally sound.)

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The Gilmour trade is probably the worst trade in club history, but these five are worth challengers for the “throne”:

  • Calgary trades Marc Savard to Atlanta for Ruslan Zainullin
    (Savard was feuding with head coach Greg Gilbert. So then-general manager Craig Button traded away Savard for an obscure Russian prospect, then fired the coach two weeks later anyway.)
  • Calgary trades Dion Phaneuf, Keith Aulie and Fredrik Sjostrom to Toronto for Matt Stajan, Ian White, Jamal Mayers and Niklas Hagman
    (The baby brother of the Gilmour trade, this was another rushed swap where the Flames gave up arguably two of the three best players in the trade.)
  • Calgary trades Brandon Prust and Olli Jokinen to NY Rangers for Ales Kotalik and Chris Higgins
    (The Flames traded Prust twice in just a couple of seasons and added a couple of negative assets in the process.)
  • Calgary trades Robyn Regehr, Ales Kotalik and a 2012 second-round pick to Buffalo for Chris Butler and Paul Byron
    (A pure cap dump so the Flames could re-sign Alex Tanguay, this one was poorly executed. Regehr was the best player in the trade, a second-rounder had to be added to get Buffalo to take on Kotalik’s bad contract, and Regehr played several more seasons at a fairly high level.)
  • Calgary trades Jay Bouwmeester to St. Louis for Reto Berra, Mark Cundari and a 2013 first-round pick
    (Bouwmeester had another full season left on his deal and no movement restrictions and this was the haul: an AHLer, an obscure Swiss goalie, and a late first-rounder.)

Which Flames trade do you think is the worst they ever done? Can any trade hold a candle to the Doug Gilmour swap? Sound off in the comments!

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