Expectations are high for the 2026 NHL Trade Deadline with Craig Conroy at the helm for the Calgary Flames. The 3rd-year general manager has been very tactical in his moves thus far. Cautious 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 that same chair. We are gonna take a look back at some of Calgary’s worst trade deadline moves and hope that Conroy avoids adding himself to this list once again this season.
The Calgary Flames trade Brett Hull and Steve Bozek to the St. Louis Blues for Rob Ramage and Rick Wamsley (March 7th, 1988)
We’ll start with one of the harder moves to really rank in the infamous Brett Hull trade. During the 1987–88 season, the Calgary Flames went into the trade deadline in need of 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 defencemen 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 tough to place. The Flames would go on to win their sole Stanley Cup in the very next season, with Rob Ramage scoring 12 points in 20 playoff games. Just 2nd to Al MacInnis in points by a Flames defenceman during that run. Ramage would only last 80 total 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 really is just up to how you want to 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 they were able to win a cup with the minimal return they got?
The Calgary Flames trade Matthew Lombardi and a 2010 1st-Round Pick to the Phoenix Coyotes for Olli Jokinen and a 2009 3rd-round pick (March 4th, 2009)
Skipping 31 years forward, we find ourselves in 2009. The Calgary Flames finished with 42 wins, and they were booted in the 1st round of the playoffs. Heading into the 2009 NHL Trade Deadline, it was clear that Captain Jarome Iginla needed a little bit more help on the top line, and General Manager Darryl Sutter thought he had just the man to do it. The Flames would move 5-year veteran Matthew Lombardi and a 2010 1st-round pick to the Phoenix Coyotes for Olli Jokinen and a 2009 3rd-round pick.
Olli Jokinen would put up 15 points in 19 games post-deadline. Not bad by any means, but it looks a bit worse when you realize that Matthew Lombardi would end up putting up 16 points in the same time span with a worse Phoenix Coyotes team. Calgary would end up losing in the 1st round once again and would trade Jokinen to the New York Rangers less than one year later. Come June 2010, the Flames would walk into the NHL Draft without both their 1st-round pick and the player they traded for with it.
The Calgary Flames trade Jarome Iginla to the Pittsburgh Penguins for Kenny Agostino, Ben Hanowski, and a 2013 1st-Round Pick (March 28th, 2013)
It was known going into the later parts of the 2012–2013 season that Jarome Iginla would most likely be moved to chase a cup. Although the aging star was beginning to slow down, he would still be an asset to any team looking to chase a cup, even if it was as a rental. While multiple contenders would show interest, it would end up being the Pittsburgh Penguins who would make the move to acquire the Flames’ captain.
With the Calgary Flames wanting to get younger, General Manager Jay Feaster accepted prospects Kenny Agostino, Ben Hanowski, and a 2013 1st-round pick that would later become Morgan Klimchuk for Jarome Iginla. Despite being promising 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 side, even though Iginla would not win the Cup with Pittsburgh, he would be a major part of their playoff run that season. Safe to say getting three AHL players for 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 & 2013 first-round pick (April 1st, 2013)
That same deadline, Feaster would move on from another veteran, Jay Bouwmeester, for even more prospects. The defencemen would head to the St. Louis Blues in exchange for goaltender Reto Berra, a defenceman in Mark Cundari, and another 2013 1st round pick, with this one becoming Emile Poirier. You may have noticed that, similarly to the Jarome Iginla trade, Feaster would receive three prospects for his vet, but shockingly, all three would also not turn into impact players.
The only one of the bunch that came close was Reto Berra, who would play with the Flames for a portion of the 2013–2014 before the Flames traded him to Colorado for a 2nd round pick. Berra would bounce around the AHL and NHL until 2018–2019, when he returned to Switzerland, where he still plays to this day. That means that Calgary went 0/6 on prospects at the 2013 Trade Deadline. Jay Bouwmeester would play seven more seasons in the NHL, winning a Stanley Cup with the Blues, and the Flames fired Jay Feaster halfway through the 2013–2014 season.
Really makes you appreciate Craig Conroy, huh?
Things can certainly be hard as a Calgary Flames fan, but it’s probably good to remind ourselves of how bad it could be. Craig Conroy has built a good system of prospects through very successful drafts and logical trades. It may still be early in his tenure, but compared to many of his predecessors, it’s safe to say he has really done well with the team that he was given. Hopefully, that trend continues through the 2026 NHL Trade Deadline. I don’t think anyone wants to see his name on this list.
