During his tenure as Calgary Flames general manager, Darryl Sutter did a lot of smart things. He acquired Miikka Kiprusoff. He assembled a pretty decent core and managed to win a few playoff rounds and hang some banners.

But later on in his tenure, the Jolly Rancher made some peculiar moves. Most notable among them: the trade that sent Dion Phaneuf out of town.

In January 2010, the Flames were a weird spot. They had made the playoffs for four consecutive seasons, but a superb November had turned into a mediocre December and the team remained as inconsistent under new coach Brent Sutter as they had been under predecessor Mike Keenan. And his predecessor Jim Playfair. And his predecessor, Darryl Sutter himself.

It became clear that a shake-up was needed. Rumours persisted that Dion Phaneuf, in his fifth year with the team, had asked for a trade. If nothing else, he had developed some bad habits and hadn’t kept maturing on the ice the way the club had hoped he would. Not a defensive stalwart, his offense was becoming less reliable. At the end of January, Sutter pulled the trigger and sent Phaneuf to Toronto.

The trade as a whole was kind of weird. Phaneuf was packaged with reliable AHLer Keith Aulie and penalty killing specialist Freddie Sjostrom to the Leafs for all-around center Matt Stajan, two-way winger Niklas Hagman, defensive defenseman Ian White and grinder Jamal Mayers.

(The post-trade press conference was astonishing, particularly one exchange where Phaneuf answered a query about where he would go from here with a deadpan “Toronto.”)

The Flames didn’t have a ton of good prospects in their system – Mikael Backlund was still a project at this point and Tim Erixon hadn’t signed – and the Flames ended up trading the 24-year-old Phaneuf, 20-year-old Aulie and 26-year-old Sjostrom for Stajan (26), Hagman (30), White (25) and Mayers (35). Nobody really looked at the Flames roster and said “If only they were older…” but that’s what happened.

They also traded away the best player in the swap and got a bunch of guys that were decent, but nobody was an upgrade on the guys they lost. White was a downgrade on Phaneuf and became more beloved for his sweet moustache and sliding block attempt nicknamed the “Ian White starfish.” Hagman was a downgrade on Sjostrom. Mayers didn’t really fit the Flames system. Stajan had good years still ahead of him, but Brent Sutter struggled to figure out what to do with him for awhile after he arrived.

The Flames missed the playoffs in 2009-10 and were well on their way to another disappointing season in 2010-11 when Darryl Sutter parted ways with the club. If only he had held onto Phaneuf for a bit longer; he was still quite young and had four seasons left on his deal. Had Sutter gone to the draft to sell off Phaneuf, it seems probable that he would’ve have netted a bigger windfall.

Stajan was a great role guy for the Flames for many years. Had he been part of a Phaneuf package that included a top prospect or high draft pick, fans would’ve been excited about him. But when Stajan is the biggest piece the club receives for arguably the best home-grown prospect they had in almost a full decade, something’s gone terribly wrong.