Expectations are high for the 2026 NHL Trade Deadline with Craig Conroy at the helm of the Calgary Flames. The third-year general manager has been very tactical in his actions so far. Careful not to pull the trigger on the wrong thing, a trait he doesn’t necessarily share with many of the previous people to sit in the same seat. We’re going to take a look back at some of Calgary’s worst trade deadline moves and hope Conroy doesn’t add himself to that list again this season.
The Calgary Flames trade Brett Hull and Steve Bozek to the St. Louis Blues for Rob Ramage and Rick Wamsley (March 7, 1988)
We’ll start with one of the more difficult moves to really score in the infamous Brett Hull trade. During the 1987-88 season, the Calgary Flames entered the trade deadline needing physicality on their blueline and a backup for Mike Vernon. Desperate to add some depth to their roster, they would move 23-year-old rookie Brett Hull and veteran Steve Bozek to the St Louis Blues for defensemen Rob Ramage and goaltender Rick Wamsley.
On paper, it’s a brutal trade for the Calgary Flames, but here’s why it’s a bit difficult to place. The Flames would win their only Stanley Cup the following season, with Rob Ramage scoring 12 points in 20 playoff games. Only 2nd to Al MacInnis in points by a Flames defenseman during that run. Ramage would only last a total of 80 games with the Flames before leaving for the Toronto Maple Leafs. Wamsley remained a backup for the Flames until they traded him to the Maple Leafs in 1992. So it just depends on how you look at it. Was it worth it for Calgary to trade someone who would become one of the greatest snipers of all time just because he could win a Cup for the minimal return he got?
The Calgary Flames trade Matthew Lombardi and a 2010 first-round pick to the Phoenix Coyotes for Olli Jokinen and a 2009 third-round pick (March 4, 2009)
Skip forward 31 years and we find ourselves in 2009. The Calgary Flames finished with 42 wins and they were booted in the first round of the playoffs. Heading into the 2009 NHL Trade Deadline, it was clear that captain Jarome Iginla needed a little more help in the top lane, and general manager Darryl Sutter thought he had the right guy to do that. The Flames would move five-year veteran Matthew Lombardi and a 2010 first-round pick to the Phoenix Coyotes for Olli Jokinen and a 2009 third-round pick.
Olli Jokinen would score 15 points in 19 games after the deadline. Not bad by any means, but it looks a little worse when you realize Matthew Lombardi would score 16 points on a worse Phoenix Coyotes team over the same period. Calgary would ultimately lose again in the first round and would trade Jokinen to the New York Rangers less than a year later. In June 2010, the Flames entered the NHL Draft without their first-round pick and the player they traded for.
The Calgary Flames trade Jarome Iginla to the Pittsburgh Penguins for Kenny Agostino, Ben Hanowski and a 2013 first-round pick (March 28, 2013)
In the later parts of the 2012–13 season, it was known that Jarome Iginla would most likely be pushed to pursue a cup. Although the aging star has started to slow down, he would still be an asset to any team looking for a Cup, even if it was a rental. Although several contenders would show interest, it would ultimately be the Pittsburgh Penguins who would make the move to take over the captaincy of the Flames.
With the Calgary Flames looking to get younger, General Manager Jay Feaster accepted prospects Kenny Agostino, Ben Hanowski and a 2013 first-round pick that would become Morgan Klimchuk for Jarome Iginla. Despite showing promise at the time, none of these prospects would ever become full-time NHLers, with all three spending the vast majority of their careers in the AHL. On the other hand, even if Iginla didn’t win the Cup with Pittsburgh, he would be a big part of their playoff run that season. It’s safe to say that getting three AHL players to be the face of your franchise wasn’t exactly a good look for Jay Feaster.
The Calgary Flames trade Jay Bouwmeester to the St. Louis Blues for Reto Berra, Mark Cundari and 2013 first-round pick (April 1, 2013)
That same deadline, Feaster would move on from another veteran, Jay Bouwmeester, for even more prospects. The defensemen would go to the St. Louis Blues in exchange for goaltender Reto Berra, a defenseman in Mark Cundari, and another 2013 first-round pick, with this one becoming Emile Poirier. You may have noticed that, similar to the Jarome Iginla trade, Feaster would get three prospects for his vet, but shockingly, not all three would turn into impact players either.
The only one of the bunch who came close was Reto Berra, who would spend part of the 2013-14 season with the Flames before the Flames traded him to Colorado for a second-round pick. Berra would bounce around the AHL and NHL until 2018-2019, when he returned to Switzerland, where he continues to play to this day. That means Calgary was rated 0/6 in terms of prospects at the 2013 trade deadline. Jay Bouwmeester would play seven more seasons in the NHL and win a Stanley Cup with the Blues, and the Flames fired Jay Feaster midway through the 2013-2014 season.
You’re really starting to appreciate Craig Conroy, aren’t you?
It can certainly be hard as a Calgary Flames fan, but it’s probably good to remind ourselves how bad it can be. Craig Conroy has built a good prospect system through highly successful concepts and logical trades. It may still be early in his tenure, but compared to many of his predecessors, it’s safe to say he’s done a really good job with the team he was given. Hopefully that trend continues until the 2026 NHL Trade Deadline. I don’t think anyone wants to see his name on this list.
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