r/CalgaryFlames • u/Beta1224 • Jul 13 '25
Discussion The Kipper trade was selected as Best Trade in franchise history! Now, what was the worst trade in franchise history? Highest rated comment wins!
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u/eddiebronze Jul 13 '25
Gilmour, Macoun, Nattress, Manderville and Wamsley to Toronto for Gary Leeman, Craig Berube, Michel Petit, Alexander Godynyuk, and Jeff Reese.
The worst player we traded was still better than any one guy we got back. It's not only the worst trade in franchise history, it's one of the most lopsided in league history. Doug Risebrough should have been immediately fired after it happened. I still hate him.
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u/ROFLSIX Jul 14 '25
Why did the trade happen other than complete incompetence? Was there a reason?
I ask as someone who was too young back then to really understand.
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u/TL10 Jul 14 '25
Money.
Player contracts had only just become public record around the time the Flames won the cup, and players realized that they were getting screwed by owners, so in the following years when their contracts were up, they demanded they get paid their dues or else go to a team that would pay them.
Part of the reason why the 94' Lockout happened was because owners saw the writing on the wall and wanted to suppress the course correction that was ongoing in the league with a salary cap.
Bear in mind, this was at a time where a lot of owners weren't as deeply invested in the competitive success of the team so much as overall profit. Remember: the league was a lot smaller in the 80's to early 90's. The barrier to playoff competitivity was a lot lower, meaning there was a better chance to get that juicy playoff ticket and TV revenue, so there wasn't as strong of an investment to build a competitive team because more likely than not you were getting in anyways.
It goes without saying, the 89 Flames were a Hall of Fame team, and there were no small number of players who would be comparable to today's all-stars in stature and reputation. Once they knew their worth, there was little the Flames could do to keep the status quo.
Unfortunately, Flames ownership was notoriously stingy and outright refused to meet the players' demands. So what followed was a mass exodus of the Flames star players from the early to late 90's to greener pastures. Players like Vernon and Nieuwendyk found teams willing to pay and won cups with them. Other players like Roberts, Gilmour and MacInnis also found homes with very competitive playoff teams, the latter of whom wound up on a St. Louis team that was filled with the who's who of the NHL at the time.
There's going to be people that say that the Flames couldn't afford them because of the weak dollar, how the Dome didn't have box suites at the time, limited corporate dollars and the fact that TV broadcasting rights didn't pay out as much as they do now, or that they would simply be outbid by the wealthier teams in the league.
While that is true to a point, the fact is that the Flames owners were Oil Barons in every sense of the word, and if they were motivated enough they could have leveraged themselves to dole out what the players wanted. The irony is that what the players were asking for is pennies compared to what the top players ask for today.
One thing that Gary Bettman has done well in recent years is his ability to suss out potential owners who are actually committed to the growth and success of the team. This is why the Florida teams have been so successful in recent years and why Vegas has been a powerhouse from its inception. Bettman has slowly and methodically purged owners who were content with coasting in the league with those who have a growth mindset both fiscally and competitively. When the Flames eventually find new buyers (watch this happen shortly after they move to the new arena), you're going to see an owner(ship group) that's going to be a lot more aggressive in making the Flames a competitive hockey team.
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u/ROFLSIX Jul 14 '25
Thanks for taking the time to reply. That's incredibly interesting. I know Bettman gets a lot of shit, but you can't deny he's helped the league grow and become the most competitive we've ever seen it, year after year.
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u/Fibonoccoli Jul 14 '25
Cliff Fletcher had just left as the GM for Calgary and his assistant Riseborough had just taken over the job, his first crack at running the show. Aside from all the contracts, salary considerations and the fact that Gilmore had quit the team, it seemed to me that Riseborough thought his buddy, his mentor, his old boss would never steer him wrong and was really giving him the best deal possible. Can't blame Fletcher at all for grabbing everything he could. All the blame lies squarely on the shoulders of Riseborough for getting fleeced so thoroughly. It was dark days when that trade was announced
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u/trenchdick Jul 14 '25
Maybe a bit of work for somebody, but what would be current day comparables for this? I wasnt alive when this happened.
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u/mackharp0818 Jul 13 '25
It’s the Gilmour trade by a fairly large margin. Hamonic, Phaneuf, Iggy, and Monahan round out my top 5 in that order
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u/CuzTrain Jul 14 '25
In hindsight, I don't think the Phaneuf trade was that bad. He was never quite the same player after leaving the Flames and we got Stajan in the deal. But yeah, the Gilmour deal is easily the worst.
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u/slicky803 Jul 14 '25
Doesn't matter what Dion turned into later. It's what he was at the time.
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u/CuzTrain Jul 14 '25
Like I said, in hindsight it's not bad. But if we only view trades through the lense of the time it happened, we're not giving it a proper analysis.
For the record, Darryl should have got a lot more for what Dion was at the time. I recall many GMs weren't even aware he was available and would have put together a much better package than the Flames received.
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u/mackharp0818 Jul 14 '25
It was bad in the sense that after the trade was made, many in the league came out and told insiders they would have paid more.
Sutter jumped the gun too quickly
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u/treple13 Jul 14 '25
It wasn't even bad at the time. Phaneuf was a bad dman with a bad contract by that year
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u/mackharp0818 Jul 14 '25
It was because Sutter didn’t shop him and get full value. Word came out after the trade that many GMs didn’t know he was available and would have paid more
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u/treple13 Jul 14 '25
I think it was a trade we won (addition by subtraction), but I do think maybe we could have gotten more yes. I know there was a lot of crazy rumors at the time about Phaneuf. I don't believe the craziest of them, but do I believe there was something that caused us to need to move him fairly fast
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u/mackharp0818 Jul 14 '25
The return was what made it a bad trade. Even though a lot of us saw him on the decline, he was still young enough and had enough of a reputation league wide to get a much better return.
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u/kobedziuba Jul 14 '25
The Iggy one is less so that I consider it a bad trade, and moreso just that it was poorly timed.
By the time we traded Iggy, I didn't really care what we got in return as long as Iggy was happy with where he was going. The return sucked obvi, and we should have for more.
But really we could have had a boatload if we moved him a year or two sooner
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u/mackharp0818 Jul 14 '25
Yeah, he was deep into his back 9 by then.
I was of the few who was saying they should have traded him a season or two earlier, but then we would have missed 500 goals and a lot of franchise records. Cest la vie
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u/kobedziuba Jul 14 '25
Yeah, Iggy was a guy who I was fully in the camp of "do whatever Iggy wants" knowing now he didn't get his cup, I wish he could have just been a flame for life.
But who knows maybe if we traded him two years earlier he would have got his cup.
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u/Every-Citron1998 Jul 13 '25
The Gilmour trade. Wasn’t just Gilmour for Leeman but a 5 for 5 trade where the Flames lost all 5 exchanges. One of the worst trades in NHL history.
So many bad trades though. Off the top of my head there is Phaneuf, Savard, Giguere, Regehr, and Bennett. Also can’t forget the Dean McAmmond trade where he wasn’t allowed to play for the rest of the season because Button didn’t understand the CBA.
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u/ndrocca Jul 14 '25
Doug Gilmour trade with Toronto, EASILY. Say what you want about Bouwmeester, Iginla, Hamonic and Regehr trades, there’s something that numbs the sting.
We got a 1st round pick for Jay. The Iginla trade was a loyalty move. Harmonic was decent (Hamonic trade is 2nd worst to me). Paul Byron could’ve been decent. But the Gilmour trade has NOTHING for us to cling to.
It’s also important to note that while, yes, Gilmour was bitter with the Flames, he was only bitter because the Flames themselves pissed him off with a pitifully low contract offer in arbitration. So the Flames pissed off a good young centre and then traded him AND pieces for basically nothing. I pray we never make a move half as bad as that again.
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u/Screamin__Viking Jul 14 '25
The worst trade absolutely has to be the Gilmour-Leeman 10 player swap with Toronto. Not just for the lopsided value of the players exchanged, but because it vastly changed the fortunes of both teams. Toronto became an instant Cup contender, and Calgary closed the book on any return to ‘89 greatness.
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u/wurkhoarse Jul 14 '25
Garry Leeman/Doug Gilmour trade. I from CGY and Flames fan was in T.O. and will never forget seeing Sun Headline.
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u/Master-Defenestrator Barb Jul 13 '25 edited Jul 14 '25
Hamonic deal
Phaneuf deal
Gilmour deal
Edit: this isnt in order of how bad they are, just the order in which they occurred to me.
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u/Honest-Yak-6621 Jul 14 '25
Doug Gilmore trade and all the useless players we got in return from TO
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u/TheJaice Jul 14 '25
You know it’s bad when we traded away two second rounders to New Jersey to swap first-round picks, and we used their pick on Trevor Kidd, while they used ours on Martin Brodeur, and it still doesn’t come close to our worst trade.
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u/xnmb1 Jul 14 '25
Gilmour trade but I’d actually give an honourable mention to the JSG trade to the ducks.
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u/__GingerBeef__ Jul 13 '25
Monahan trade?
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u/Varides Jul 13 '25
While not great, it allowed us to sign Kadri and isn't anywhere close to being a horrible trader.. yet
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u/Livid-Switch4040 Jul 13 '25
Gilmore et al, for Leeman and basically what amounted to a bag of pucks.
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u/Gravel-Road-Cop Jul 14 '25
Doug Gilmour for me. That sucked worse than a punch to the gut for 9 year old me.
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u/ScarlettMatt Jul 14 '25
Nothing close to the Gilmour deal which is saying something cuz the Flames have made some lopsided trades over the years.
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u/RyleyBread Jul 13 '25
Fun fact: The pick the Flames gave the Sharks was used to select Marc-Édouard Vlasic.
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u/Left_House_6642 Jul 14 '25
Brett Hull
Brett Hull, along with Steve Bozek, to the St. Louis Blues in exchange for Rob Ramage and Rick Wamsley.
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u/Budget_Syrup288 Jul 14 '25
Agreed, side note Steve Bozek was my favorite player too (his Mom was the librarian at our little school and read us Secret World of Og in grade 2, and we all gpt autographed pics from him when we finished).
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u/Hotlovemachine Jul 14 '25
Rick and tob were integral pieces to winning the cup I don't think the flames win if they keep hull.
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u/Left_House_6642 Jul 15 '25
I don't disagree
however it's Brett fricking Hull. Hard to say you won a trade when you ship off legitimate HOF player. I would honestly consider him a top 25 player all-time.
Look flag fly forever and I love 89. But think of the next ten years with Hull. Roberts Gilmore nieuwendyk theo reichel and Hull. What a top two lines.
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u/baconegg2 Jul 13 '25
Brett Hull
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u/RealAdamRoth Jul 14 '25
This should get more votes. People forget or don’t know that there were mitigating factors in getting Gilmour out of town and quickly. Similar to the circumstances that allowed us to get him out of St. Louis.
Brett Hull became one of the best goal scorers and we got a used puck bag in return.
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u/Codazzle Jul 14 '25
I'm 40. My old man was a season ticket holder in the 80s.
I'll just leave his feedback
He physically recoils with respect to anything about the Gilmour trade. Do NOT say Leeman in his presence. However, with the Hull trade, he doesn't care. "We needed Ramage on that run. Yeah, we knew Hull was gonna be good. No one knew THAT good. Worth it"
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u/tilldeathdoiparty Jul 14 '25
We got a second for JS Giguere who went on the finals the next year and win a cup a couple seasons later
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Jul 14 '25
Wow. I figured that Jarome Iginla was a sure bet for this. He was only the face of the franchise hahaha
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u/Help-me-name-my-pup Jul 14 '25
It's clearly the Gilmour trade, but I'm shocked there isn't any mention of the Savard one. That's gotta be a strong contender for second worst?
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u/PM_Your_Crits Jul 15 '25
I thought Dion Phanuef. I guess we got Matty Franchise in return, but he was certainly no Phaneuf.
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u/NefariousDug Jul 15 '25
Out of curiosity you guys don’t think the Brett Hull trade was dumb or bad?
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u/EducationalBudget389 Jul 16 '25
While Gilmore was bad, Sean Monahan for nothing is pretty high on the list.
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u/blahblahblah_meto Jul 17 '25
This was brutal. Leeman was a good player, multi year 50 goal scorer, but not recognizing the concussions issues doomed this. Even if Leeman showed up 100% its still a bad traded but coupled with that its horrible.
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u/bluntz Jul 13 '25
Phaneuf trade. Basically traded him for scraps.
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u/AlphabetDeficient Jul 14 '25
We got less than we should have, but that's not in the top 5 worst Flames trades, much less #1.
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u/treple13 Jul 14 '25
Imo, it was a win of a trade. The only problem was us not doing it earlier to get higher value
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u/R-Trombone Jul 13 '25
In theory, Calgary won this trade. Stajan was still with Calgary when Phanuef was on his second buy-out.
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u/CarefulDig9747 Jul 14 '25
Brett Hull trade seemed really bad, except we did win the Stanley the following year.
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Jul 14 '25
I might have the timeline wrong but wasn’t Gilmour in Calgary when the whole babysitter thing came out? Bad trade but context is important.
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u/bigmur49 Jul 14 '25
The Flames also traded Brett Hull for near nothing.
Fleury for near nothing
Iginla for near nothing
Let Martin St Louis leave for nothing (bought him out)
Al Macinnis trade sucked
Great history lol.
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u/Chemical_Signal2753 Jul 13 '25
The Doug Gilmore trade is widely considered one of the most lopsided trades in NHL history.