When Sergei Fedorov chose to sign with the Ducks, leaving the only US home he'd ever known. Mike Ilitch said it best when he said he was certain Sergei would retire in Detroit and that #91 was going to hang from the rafters one day. Regrets all around today, I am sure.
I was devastated when Fedorov left. It took me months to recover. In the long run, though, it was for the best, how else would the Wings have all the players they do now under the Cap?
Wendel Clark and Douggie Gilmour, I'm sure I speak for all Leafs fans when I mention them.
They bled blue and white.
Douggie skated every shift like his life depended on it, I'll never forget the Leafs having an oxygen bag on the bench for Douggie after a playoff game that had gone into the 3rd OT. It seemed like he never left the ice, and when he did he practically fell onto the bench... but he was always up again ready to take to the ice in another second.
Clark was the heart and soul of the Leafs for a long time. Tough and gritty, there were times the Leafs took to taping the stick to his gloves to ensure he wouldn't drop the stick to fight anyone because he was so tough he could double as an enforcer but as our only decent player we absolutely needed him out on the ice.
For me personally... Cujo. My all time favourite player. I've never been happier as a hockey fan then when Cujo first signed as a Leaf and never been more depressed then when Belfour (Someone I strongly dislike) signed as his replacement.
When I was a kid, the one player who I wanted to play like was Doug Gilmour. He's everything I wish I was in a hockey player.
Haven't had a "favorite player" since he left Toronto.
When I was growing up, I was a huge Montreal Canadiens fan (my dad and brothers were big Canadiens fans).
I also was a huge Kirk Muller fan, even before he came to Montreal. He was my favourite player even when he played for the Devils (I had a Devils jersey with the #9 on the back of it that I used to wear all the time while playing street hockey).
So saying all of this, it is easy to see why it broke my heart when Muller was traded from the Canadiens. Muller on the Canadiens was a dream come true. Muller being traded from the Canadiens was heartbreaking.
What made it even more heartbreaking is the fact that Montreal had apparently promised him that under no circumstances would he be traded.
I'm somewhat in the same boat you are...but I'm on the opposite side of the spectrum. I was devastated when Pierre Turgeon was traded to the Canadiens for Muller. It was like, 1994, and I idolized Pierre growing up. It was the beginning of the end for the Islanders, cuz everything surrounding the team collapsed after the Turgeon trade. The fisherman jersey disaster began that next season, the salary dumps, the losing records, the very messy ownership squabbles, etc, etc. And it adds salt to the wounds with how Muller was treated by/had treated the Islanders. It was just a disaster.
The Turgeon/Muller trade ranks as one of, if not the worst trade in Islanders history. And there are not many Islander fans that got over the loss of Turgeon. For me especially, it was extremely difficult.
As an Oilers fan, there are many. Recentley, I'd have to say Weight getting traded to St Louis. He was our captain and the Oil looked like they were on the vurge of turning the corner. Joseph signing with Toronto was another one...we haven't won a playoff series since he left.
Any time a small-market team lost a player to a larger-market team for financial purposes, it would break my heart. But if I had to pick one, it's definitely Gretzky leaving for L.A. (and I'm a Habs fan).
Selanne to Anaheim for Oleg Tverdovsky and Chad Kilger.
God, I can't even type that second one without getting irritated. Ten years later and I STILL wouldn't make that deal!
In fairness, you are benefitting from hindsight. I remember thinking that Winnipeg might have made out ok on that deal. Tverdovsky was already in the league and looking like he would continue developing into the slick skating/passing defensemen that was a potential Norris guy.
Kilger was also young and a top 5 draftee who wasn't even being hinted as a bust.
Obviously that's not the way it worked out, but the deal was typical from a small-market perspective. It would be akin to a Naslund for Pitkanen + Richards deal today.
definitively Patrick Roy! when he got traded he was something like 8 years old and i didn't understand the situation with Tremblay and the fans, at the moment the only thing i used to know was that he was traded and i think that i cried 2 or 3 days...serious!
When Selanne was traded to the Sharks for Steve Shiedls and Jeff "I'm too good for Anaheim" Friesen, I got upset, but it was somewhat expected since the team sucked.
Kariya turning down and then leaving the Ducks after making the Finals, to have a better shot at the Stanley with the Avs (making just 1,2 millions) was tremendous for every Duck fan.
I still hate him for that.
Not only was Deadmarsh the epitome of a hockey player, he was finally coming into his own as a star offensive player. When Deadmarsh was injured that year he was tied with Naslund for the league lead in goals.
2. Gretzky traded to St. Louis
I never cared much for the Blues and it was tough seeing my childhood hero go there, plus the Kings return in that trade was horrendous.
3. Marty McSorely's illegal stick
It makes me sick even thinking about it..no more comment.