I was technically around when Risebrough was GM, but too young to be really dialed in. Plus, it was a time before the internet and I lived outside of the Calgary media market. I was pretty much deaf to anything going on from a management side, so it's hard for me to judge what was really going on.
I just know it was in the pre-cap era when players were holding out all the time and small market Canadian teams were struggling economically and were having trouble keeping players. The rules were also different as you could renegotiate contracts and trade players for cash for example. The former gave players leverage in some situations (Gilmour for example). It's easy to look back at the Gilmour trade as terrible, but he also put the Flames in a bad situation and it's hard to know what else was being offered at the time combined with the pressure to win as the Flames were is a window that was closing. I'd be curious to know from people who lived in the Calgary media market at that time if there were other rumoured potential trades that could have been taken instead.
If parity existed back then and Risebrough had the tools to compete on something closer to a level playing field with the big market teams, I bet different decisions would have been made.
Probably some recency bias, but Treliving has to be up there for me. He had all the tools to compete and still made some bad decisions that set the team back. Craig Button as well for how he dealt with the Savard/Gilbert situation (which even he now admits as wrong), and for buying out St. Louis who was on the cheapest possible contract at the time. I know no one ever thought St. Louis would go on to do what he did, but he was a good player down the stretch the previous season and there was some optimism around him going into the offseason, comparable to Klapka right now you could say. No one is expecting 100 points from him, but there were all the reasons in the world to see what's there at least. Instead he bought him out and brought in Dwayne Hay, Blake Sloan or whoever it was. I remember thinking at the time that he must have not paid any attention to the Flames before being hired. Imagine that 2004 team with Savard and St. Louis on it?
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"A pessimist thinks things can't get any worse. An optimist knows they can."
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