Speculation: Craziest trades that almost happened

[SomeDude]

In 3rd grade, I almost traded my grapes for another kid’s dunkaroos until the teacher had to step in to stop the fleecing. I often wonder what could have been.

 

[smitty10]

Difference was the team was bad having finished 7th OA in back to back years. And were destined to be the same or worse. Charelli publicly said they chose TOR instead of NSH because they knew the picks would be high. Burke even asked his scouts if they rather have Hall/Seguin or Kessel. Everyone and their mother knew it was a crazy trade at the time. When the Leafs traded Kaberle it was at the TDL and Colborne at the time was considered a B prospect with not much upside. The pick thry got was always going to be a late 1st, which does not hold the same value as two likely top 10 picks. So if anyone is being disingenuous it's you.

Here again with the revisionist history. As if anyone knew the 1st pick would be a 2nd overall pick and that Boston would pick Dougie Hamilton a year later as your first post suggested. Had Boston selected Duncan Siemens, we wouldn't be having this conversation.

We all know in hindsight that this trade was lopsided. To suggest that anyone thought the Leafs were going to bottom out in that first year though is absurd. The trade was made to make the Leafs better immediately, which it failed to do. With that being said, most people at the time felt the Leafs would be a 8-10 team, not a 14/15 team.

 

[Petes2424]

It was either the night he was traded to Colorado or the night before he was traded the next morning….

They were reporting in Detroit, that Ray Bourque was going to be traded to the Wings for Tomas Holmstrom and other pieces. It was supposedly a done deal, to be announced the following morning I believe. Then the next morning, it was announced Colorado got him. It wasn’t speculation. They were reporting it was done…. I remember getting phone calls about it late at night. I’m pretty sure it was the next morning we found out the Colorado thing but many went to sleep in Detroit that night, thinking the Wings were getting Bourque.

 

[ForsbergForever]

Patrick Roy for Stephane Fiset + Owen Nolan,
Serge Savard was fired before the trade was done

I've also heard versions where Adam Deadmarsh was also part of the package.

 

[lawrence]

cant say for sure it almost happened, but we did through a huge offer for Brad Richards.

Canucks offers up the 24th pick Bourdon, Grabner and Schneider for the 3rd pick which was projected to be BC Boy Kyle Turris. Plenty of Bure rumours

Greg Adams,
Kirk Mclean,
2 1st round picks
14 million dollars for

Wayne Gretzky.

 

[Oddbob]

well your wrong. this was well before the wings starte ghaving success

Absolutely not wrong. Even before they had success, the Iliitch's loved Yzerman and considered him family, which is why he never got traded to Ottawa for Yashin in 1995. There is no way they were trading a franchise forward for a just good NHL goalie, who shortly after his good start in Philly he became a very average goalie. Yzerman was also a huge reason they got out of the Dead Wings era, and no longer had to giveaway cars to get people to come watch the Wings.

 

[Oddbob]

It was always speculated on by fans and radio hosts but I’m not sure it was ever actually discussed by the teams. Maybe though.

Before the 97’ Cup, there was actually a large percentage of Detroit fans who truly believed the Wings would NEVER win with Yzerman leading the team. Media members too. I remember them always bringing up Lafontaine, suggesting he would want to win for Detroit more than Yzerman. I’ve never heard it actually made it to managers discussing it though. Those people are obviously hard to find these days but they were very vocal back in the day.

The Ottawa one however, was very real and almost happened. Yzerman for Martin Straka and some other pieces and draft picks but Straka was the main name at the time.. That one has been confirmed many times. To the extent someone had said they leaked it to see the reaction from fans. I remember it being out there as “imminent.”

I don't buy that the Wings were seriously interested in this trade. Lafontaine had worse stats to this point than Yzerman and was no better at defence than Yzerman so that trade wouldn't have made sense. Though I can't believe that Bowman wanted Yashin over Yzerman either, as it is hard to imagine someone described as a genius in Bowman thinking that makes the Wings better. Yashin was never better offensively and had poor compete a lot of the time, something I have never heard Yzerman complained on about. Yashin also sucked in his own end, not sure how Bowman thought we win with Yashin suddenly learning to play more defence.

 

[Jumptheshark]

Tyler Myers for Connor Bedard might still happen

Lol

Absolutely not wrong. Even before they had success, the Iliitch's loved Yzerman and considered him family, which is why he never got traded to Ottawa for Yashin in 1995. There is no way they were trading a franchise forward for a just good NHL goalie, who shortly after his good start in Philly he became a very average goalie. Yzerman was also a huge reason they got out of the Dead Wings era, and no longer had to giveaway cars to get people to come watch the Wings.

The only time I can remember ANY serious talk of Stevie Y getting traded was when the Gretz trade talk first happened. Other than that I can not find any. One of the oilet writers suggested it was stevie y and a first and no money

 

[Oddbob]

Lol


The only time I can remember ANY serious talk of Stevie Y getting traded was when the Gretz trade talk first happened. Other than that I can not find any. One of the oilet writers suggested it was stevie y and a first and no money

Considering what Gretzky returned it wouldn't have taken Yzerman to get Gretzky. The no money part is for sure why that isn't really a legit rumour as Pocklington took what he got player wise cause he only wanted money for his business problems. Philly, NYR, Detroit and Vancouver were the teams other than LA according to Gretzky and all of them would have involved heavy money as that is all Pocklington cared about. The Yashin/Yzerman trade is legit as Bowman said years later he was making that trade, and the Illitch family shut it down.

 

[Axel Sandy Pelikan]

It was always speculated on by fans and radio hosts but I’m not sure it was ever actually discussed by the teams. Maybe though.

Before the 97’ Cup, there was actually a large percentage of Detroit fans who truly believed the Wings would NEVER win with Yzerman leading the team. Media members too. I remember them always bringing up Lafontaine, suggesting he would want to win for Detroit more than Yzerman. I’ve never heard it actually made it to managers discussing it though. Those people are obviously hard to find these days but they were very vocal back in the day.

The Ottawa one however, was very real and almost happened. Yzerman for Martin Straka and some other pieces and draft picks but Straka was the main name at the time.. That one has been confirmed many times. To the extent someone had said they leaked it to see the reaction from fans. I remember it being out there as “imminent.”

Huh. Never heard Yzerman for a package headlined by Straka.

Yzerman and Osgood for Yashin, Damian Rhodes, and some pieces.

I don't buy that the Wings were seriously interested in this trade. Lafontaine had worse stats to this point than Yzerman and was no better at defence than Yzerman so that trade wouldn't have made sense. Though I can't believe that Bowman wanted Yashin over Yzerman either, as it is hard to imagine someone described as a genius in Bowman thinking that makes the Wings better. Yashin was never better offensively and had poor compete a lot of the time, something I have never heard Yzerman complained on about. Yashin also sucked in his own end, not sure how Bowman thought we win with Yashin suddenly learning to play more defence.

At the point it was rumored, Lafontaine and Yzerman were basically neck and neck. It would have been in the early 90s when the Bryan Murray Wings were the current Maple Leafs, unable to do a damn thing in the playoffs after running roughshod through the regular season scoring up a storm.

That time Steve Yzerman ripped Detroit Red Wings over trade rumors

There was a time Steve Yzerman was so angry he welcomed a trade from the Detroit Red Wings

www.freep.com

“There was talk between Buffalo and Detroit about LaFontaine for Yzerman even up,” Devellano said in 2019. “There were talks. We didn’t make it happen. But it was considered.” Ultimately, Ilitch nixed the trade.

I guess also in there, it does support Petes' assertion. There were many names bouncing around in the Senators deal. So Straka could have been a key piece instead of Yashin. As it turns out, Ottawa was owned by broke assholes then too and couldn't pay Yzerman so no amount of theorycrafting made a difference.

Both Yzerman for Lafontaine and Yzerman to Ottawa seemed kind of motivated by local kid stuff. The Wings wanted Lafontaine because he was a Waterford kid who would be a functional Yzerman equivalent in their eyes (seriously, their stats are actually quite close at that time frame). Ottawa wanted Yzerman because they were a broke, jank expansion franchise and they wanted hometown hero Stevie Y to fill the rink.

 

[blackjackmulligan]

Absolutely not wrong. Even before they had success, the Iliitch's loved Yzerman and considered him family, which is why he never got traded to Ottawa for Yashin in 1995. There is no way they were trading a franchise forward for a just good NHL goalie, who shortly after his good start in Philly he became a very average goalie. Yzerman was also a huge reason they got out of the Dead Wings era, and no longer had to giveaway cars to get people to come watch the Wings.

it was reported in the philly media.

 

[Jumptheshark]

Considering what Gretzky returned it wouldn't have taken Yzerman to get Gretzky. The no money part is for sure why that isn't really a legit rumour as Pocklington took what he got player wise cause he only wanted money for his business problems. Philly, NYR, Detroit and Vancouver were the teams other than LA according to Gretzky and all of them would have involved heavy money as that is all Pocklington cared about. The Yashin/Yzerman trade is legit as Bowman said years later he was making that trade, and the Illitch family shut it down.

Sather is the one who said the wings balked at the money

 

[Axel Sandy Pelikan]

it was reported in the philly media.

Good for them. The Wings weren't trading Steve Yzerman for Ron Hextall. The only time that Hextall and Yzerman legitimately crossed paths in maybe swapping was as GMs when Philly was hoping to reach out to Yzerman to get him to replace Hextall running the team.

 

[Oddbob]

Huh. Never heard Yzerman for a package headlined by Straka.

Yzerman and Osgood for Yashin, Damian Rhodes, and some pieces.

At the point it was rumored, Lafontaine and Yzerman were basically neck and neck. It would have been in the early 90s when the Bryan Murray Wings were the current Maple Leafs, unable to do a damn thing in the playoffs after running roughshod through the regular season scoring up a storm.

That time Steve Yzerman ripped Detroit Red Wings over trade rumors

There was a time Steve Yzerman was so angry he welcomed a trade from the Detroit Red Wings

www.freep.com

“There was talk between Buffalo and Detroit about LaFontaine for Yzerman even up,” Devellano said in 2019. “There were talks. We didn’t make it happen. But it was considered.” Ultimately, Ilitch nixed the trade.

I guess also in there, it does support Petes' assertion. There were many names bouncing around in the Senators deal. So Straka could have been a key piece instead of Yashin. As it turns out, Ottawa was owned by broke assholes then too and couldn't pay Yzerman so no amount of theorycrafting made a difference.

Both Yzerman for Lafontaine and Yzerman to Ottawa seemed kind of motivated by local kid stuff. The Wings wanted Lafontaine because he was a Waterford kid who would be a functional Yzerman equivalent in their eyes (seriously, their stats are actually quite close at that time frame). Ottawa wanted Yzerman because they were a broke, jank expansion franchise and they wanted hometown hero Stevie Y to fill the rink.

In the early 90s, they were not close at all in pts.

At the end of 1991-1992

Yzerman had 903 PTS in 673 GP - Pace of 1.34
Lafontaine had 659 PTS in 587 GP - Pace of 1.12

If they played the same amount of games that is 150+ less pts.

The next season Lafontaine had a monster 148, but Yzerman had 137.

Before his knee injuries and focusing on defence Yzerman was bested by only Gretzky and Lemieux offensively.

 

[Axel Sandy Pelikan]

In the early 90s, they were not close at all in pts.

At the end of 1991-1992

Yzerman had 903 PTS in 673 GP - Pace of 1.34
Lafontaine had 659 PTS in 587 GP - Pace of 1.12

If they played the same amount of games that is 150+ less pts.

The next season Lafontaine had a monster 148, but Yzerman had 137.

Before his knee injuries and focusing on defence Yzerman was bested by only Gretzky and Lemieux offensively.

I was speaking entirely in 90-93. Yzerman was undoubtedly a superior player before his knee injury. But he was injured by that point already. And ppg, Lafontaine and Yzerman were riding pretty close in his first Buffalo season.

Yzerman was ludicrous in the 80s. They had drawn even by the first years of the 90s on an annual basis. Lafontaine was several seasons worth behind, but he was a 1.5 ppg guy at that time.

If they had wanted him anyway and were concerned about Yzerman’s leadership at that point (seems crazy to think now, but those were legitimate discussions in the early 90s)… that wasn’t a crazy deal

 

[Billdo]

Gomez for Datsyuk

 

[TOGuy14]

This one always seemed crazy to me, even at the time

How highly did the Blue Jackets value defenseman Ryan Murray before taking him with the No. 2 overall pick in Friday's first round of the NHL Draft? Enough to turn down an eye-opening offer from the New York Islanders, who, according to numerous NHL sources, offered all of their picks -- one in each round -- for the right to move up from No. 4 to No. 2 for Murray.

That's right, for the Jackets' No. 2 pick, the Islanders offered pick Nos. 4, 34, 65, 103, 125, 155 and 185.

 

[FerrisRox]

Lol


The only time I can remember ANY serious talk of Stevie Y getting traded was when the Gretz trade talk first happened. Other than that I can not find any. One of the oilet writers suggested it was stevie y and a first and no money

There were fairly serious conversations during the 1995 lockout between the Montreal Canadiens and the Detroit Red Wings that would have sent Yzerman to the Habs for a package centred around Mathieu Schneider.

 

[GRob83]

I don't know exactly what was offered by Boston but there is a pretty funny video from the 2006 Draft where they were trying to move up to #4. George McPhee comes back to the draft table and talks to the head scout. He tells him "they want the Swede", has a good laugh and drafts Backstrom leaving the Bruins to take Kessel. The very next year the Bruins, seemingly still trying to get a center, drafted Zach Hamill. The very next pick was Logan Couture to the Sharks. Ouch.

 

[Brodeur]

I don't know exactly what was offered by Boston but there is a pretty funny video from the 2006 Draft where they were trying to move up to #4. George McPhee comes back to the draft table and talks to the head scout. He tells him "they want the Swede", has a good laugh and drafts Backstrom leaving the Bruins to take Kessel. The very next year the Bruins, seemingly still trying to get a center, drafted Zach Hamill. The very next pick was Logan Couture to the Sharks. Ouch.

I found a higher quality video recently but can't seem to find it, but Boston offered #5 and #37 for #4.

It was rumored that Boston wanted Thomas Hickey at #8 in 2007, which was the reason why the Kings didn't trade down from #4 and reached for him there instead. There was video of St. Louis offering #9 and #24 to Edmonton for #6 because they wanted Jakub Voracek. I can only assume they made the same offer to LA but the Kings didn't want to risk trading down and missing out on Hickey. After the draft, Kings GM Dean Lombardi mentioned that they had looked to move down but it didn't materialize.

Funny story with the Couture pick. San Jose GM Doug Wilson had strong ties with the Ottawa 67's where Couture was playing. Word trickled out that Couture was going to be taken by Florida at #10. San Jose didn't have a first rounder entering that draft, but on the morning of they acquired #13+ from Toronto for Vesa Toskala and Mark Bell.

When St. Louis was unable to trade up for Voracek, they pivoted as they figured they could trade down and get their next target (Lars Eller). San Jose knew they had to leapfrog Florida for Couture and they ended up getting pick #9.

 

[BostonBob]

In 3rd grade, I almost traded my grapes for another kid’s dunkaroos until the teacher had to step in to stop the fleecing. I often wonder what could have been.

What flavor did that other kid have - if it was chocolate you were definitely fleecing him.

 

[Colezuki]

Draisaitl + 4th (Puljujarvi)
For
Subban + 9th (Sergachev)

The draft that year was supposed to end with Puljujarvi going 3rd and from what was shared the Habs nearly traded Subban for Draisaitl (before he was who he is now) and PLD. I've heard variations however on if the 9th was or wasn't included but would've been a crazy trade in retrospect

 

[Tanknation]

Gomez for Datsyuk

Yikes. But what Montreal traded for Gomez in real life has to be up there for terrible trades of all time.

 

[FerrisRox]

Yikes. But what Montreal traded for Gomez in real life has to be up there for terrible trades of all time.

The Canadiens lost that trade but I wouldn't have it in my Top 100 Bad Trades of all time, let alone having it "up there."

 

[4thline]

The trade itself wasn't wild, but the repercussions would have been. Prior to the Kessel deal that happened Burke and Chiarelli thought they had a deal in place at the draft.
Burke thought it was Kaberle for Kessel and 25
Chiarelli thought it was Kessel for Kaberle and 7.

If Burke's trade goes through the Leafs add Kessel, keep their 1st's in 2010 and 2011 and add a 25th overall in 09.

The next decade fundamentally changes.