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The Calgary Flames had some problems way back in 2011. Some were market-based. Some were self-inflicted. But the fifth-worst trade in club history was a swap that somehow made things worse for the team at a time where they were trying to maximize their veteran core’s on-ice value.

Jay Feaster became fully-fledged general manager of the Flames in December 2010 when the club parted ways with Darryl Sutter. Feaster inherited a weird reserve list: a weak farm system and a rapidly aging (and expensive) core group that was a product of a lot of deficit spending of picks and prospects by his predecessor.

The fifth-worst swap is best understood as some very odd asset management. The best way to frame it is like this: Feaster seemed to think that the key to maximizing Jarome Iginla’s remaining years was with Alex Tanguay on his flank. Heading into the 2011 NHL Draft, Tanguay was a pending unrestricted free agent and the Flames wanted to avoid him going to open market.

At the time, the club had a few ugly contacts – a feature of several Sutter acquisitions – such as Ales Kotalik and Niklas Hagman at $3 million apiece. They also had a blueline that was getting a bit long in the tooth, but few younger bodies in the system to replace them.

So at the 2011 NHL Draft, here’s what Feaster put together: the Flames sent Robyn Regehr, Ales Kotalik and a 2012 second round pick to the Buffalo Sabres in exchange for Chris Butler and Paul Byron. (Regehr agreed to waive his no-trade clause to make the swap happen.) Put differently, they sent a reliable top four defender, an awful contract and a second round pick as a sweetener to Buffalo for a depth winger with 8 NHL games to his name and a reliable depth defender with questionable upside.

From a cap standpoint, the move opened up roughly $5.8 million in new cap space. The swap allowed the Flames to re-sign Tanguay to an extension before free agency opened and have some breathing room to add further pieces. (They used the room to add Scott Hannan and give Anton Babchuk a raise.)

From a hockey standpoint, the move was puzzling. Butler was a downgrade on Regehr (younger, but not better) and it took Byron four seasons before he came a full-time NHLer in Calgary. (And then they lost him on waivers for nothing.) Even worse, the move continued a stretch of deficit spending on picks. Moving the 2012 second rounder so Buffalo would take on Kotalik’s contract led to the Flames trading down in the first round that year and controversially taking Mark Jankowski. Had they not moved their second already, they might not have had the same temptation.

Locking down Tanguay to a lengthy extension also showed a bit misread on what the Flames’ core had left in the tank. The team had missed the playoffs for the prior two seasons. They signed Tanguay for five seasons, missed the playoffs for the first two seasons and then finally began the rebuild and lost Miikka Kiprusoff, Jay Bouwmeester and Jarome Iginla. Left without a role Tanguay was sold off to Colorado rather than linger during an extended rebuild, in a trade that made Shane O’Brien and David Jones part of the Flames

Someway, somehow, just about every part of the Regehr trade to Buffalo didn’t work out for Calgary. It worked out great for Regehr, though. He was traded to Los Angeles a couple years later and eventually won a Stanley Cup before retirement.