Blockbuster trades that went bad for both teams

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The only reason it did not turn out poorly is because Subban had a very short career. Weber played about 200 games for Montreal and the only thing that "saved" this trade is the COVID play-in and weak Canadian division.
Those things happened though, so therefor both teams benefited from the trade.
 

In the summer of 2008, Andrej Meszaros was an RFA after three productive seasons in Ottawa. Sens were up against the cap and didn't have the space to meet Meszaros' asking price.

Meanwhile Tampa Bay had new ownership fresh off of drafting Steven Stamkos. After trading away Dan Boyle, they wanted to get a young established defenseman who could be a cornerstone with Stamkos. So they decided to target Meszaros.

The rumor was that Tampa and Meszaros' agent had agreed to terms but they couldn't sign an offer sheet because Tampa had previously traded its 2009 3rd rounder which was a required part of the compensation. Allegedly Tampa tried to get it back from Pittsburgh, but Ray Shero thought he was doing the honorable thing by not trading it back and being an enabler.

Ottawa was a season removed from a SCF appearance so they understandably thought they were still a contender. So instead of just accepting Tampa's 2009 1st and 2nd via trade, they wanted an NHL D to replace Meszaros. Right before training camp started, Ottawa agreed to trade Meszaros to Tampa for Filip Kuba and San Jose's 2009 1st.

Tampa remained in the basement as Meszaros' offense would dry up. After a couple seasons, newly appointed GM Steve Yzerman would trade him to Philadelphia for a 2nd round pick.

Meanwhile Ottawa quickly dropped from contender status and would miss the playoffs. Kuba seemingly played decently but he was already in his early 30's when he was traded. Sens GM Bryan Murray would deal San Jose's 2009 1st for Mike Comrie and Chris Campoli.

Had they accepted Tampa's 2009 1st, Ottawa could have had Victor Hedman. That Tampa ownership lucked out by its own lack of foresight; They'd end up selling the team after just two years. I can't help but notice that bad owners seem to be a common thread in these bad trades.
 
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Iginla to Pittsburgh. Seemed to work out bad for the teams and Iggy.

Flames got a shitty return for the face of the franchise in a late first who never amounted to anything and spare parts. Iginla lost out on a trip to the finals against the Bruins who he was almost traded to while never quite finding a fit in Pittsburgh and walking as a UFA.
 
Easier with hindsight, but would be interesting to know how they would have done in 2000 with Modin/Sullivan/Cote instead of Khristich/Cross.

Those trades still baffles me like 25+ years later.

Giving up on Modin after 3 seasons, only to see him flourish in Tampa scoring 30+ goals and being one of their best players on their cup run hurt.

At least Cory Cross was more useful than Khristich
 
Trading Subban for Weber definitely didn't turn out poorly for Montreal.

He was an outstanding addition to to the team and played a huge role in leading that Canadiens team to the Stanley Cup Final.

Didn’t turn out too poorly for Nashville either. Made the Cup finals, was a Norris finalist, and they traded him before he truly fell off a cliff.
 

This was early into my hockey fandom, so I might not have the best barometer for this one. Before the rules changed in the 1995 CBA, there were two different pools for RFA offer sheets. Group II (which would survive) had the predefined draft pick compensation that's still used today. But Group I (based off of age and service time) had no predefined compensation and the wild thing was that the original team had no right to match.

If a player signed a Group I offer sheet, the two teams had a short window to work out a de facto trade (process was called equalization). If an agreement wasn't reached, the two teams would present their offer/request before an arbitrator who would pick one.

With the CBA set to expire in September 1994, St. Louis signed Petr Nedved to a Group I offer sheet in May 1994. Nedved had sat out the entire season. In the moment, Nedved was 22 and had a breakout 38 goal season to go with the pedigree of being a recent 2nd overall pick. Vancouver requested Brendan Shanahan as compensation while St. Louis offered Craig Janney and a 2nd round pick. The crazy thing is that Nedved played three games with Shanahan/Janney before the arbitrator made his ruling which made for an odd dynamic since one of them was about to be given to Vancouver.

The arbitrator chose the St. Louis offer, but Janney refused to report. Since the playoffs were looming, Vancouver didn't have the luxury of waiting out Janney like New Jersey had when Scott Stevens initially declined to show up in 1991 under the same circumstances. Vancouver would trade Janney back to St. Louis for Jeff Brown, Bret Hedican, and Nathan Lafayette.

Vancouver did benefit initially as all three were on the roster that helped make the 1994 SCF. But Lafayette would be dealt a year later for goalie Corey Hirsch. Brown was traded in late 1995 for Frantisek Kucera and Jim Dowd. So maybe not the ideal return you'd want for a 22 year old Nedved.

Meanwhile Nedved's stay in St. Louis would be short although out of his control. St. Louis would hire Mike Keenan in summer 1994 despite being under contract with the Rangers. The situation was messy and eventually the league had the two teams work out a swap as compensation. Nedved would be sent to New York for Esa Tikkanen and Doug Lidster. Tikkanen would be traded in 1995 for a 3rd. Lidster would be traded back to the Rangers in 1995 for Jay Wells.

Out of the whole ordeal, this was the final tally for both sides:

Vancouver: Bret Hedican (310 games), Jeff Brown (72 games), Nathan Lafayette (38 games), Frantisek Kucera (26 games), Jim Dowd (38 games), Corey Hirsch (101 games)

St. Louis: Petr Nedved (19 games), Esa Tikkanen (54 games), Doug Lidster (37 games), Jay Wells (76 games), and 2+ dysfunctional seasons with Mike Keenan
 
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Kind of want to say the Evander Kane trade. Jets still have assets from the trade, but the main ones pretty left.

I guess if one takes the PLD deal with Roslovic going the other way as part of it, the pieces from LA are tied back to it. But that still seems more from the Laine value than the Roslovic value. Other than that, I don't think there is much of tie left to the Jets out of all that -- Lemieux went for Hayes who went for a 5th that didn't sign. Myers left in free agency. Armia and Mason got shipped out as budget moves with draft picks for a guy who hasn't been in NA in years. Chisholm, who they picked with the pick from dealing Stafford to the Bruins went as a waiver claim to the Wild. I guess including Roslovic gets PLD and that means he's part of the Iafallo/Vilardi/Kupari/Freij return?

Murray wanted the Kings' style of punish defense and instead he got Temu Drew Doughty in Bogosian and a bunch of bad publicity with EKane who he wanted to ride shotgun for McDavid. In the end they got a badly broken defenseman and moved on from Kane when his off-ice stuff in Buffalo got to be too much.

The Sabres have Stiven Sardarian left on their reserve list drilling down to what they got (the pick for Kane went in the Montour deal, the pick for Sardarian they got back when they sold low on Montour). Ultimately kind of meh.
 
I feel like the Seth Jones trade did not work out real well for either team.

It ends up being Jones and Nolan Allan for Boqvist, Bean, Jiricek and Cole Sillinger

Hawks are looking to trade Jones now. Allan has some potential as a bottom pairing guy. Sillinger has been alright for the Jackets and the other three are gone.

Generally who gets the best player in a trade ends up winning the trade. So Columbus loses by trading a top-pairing Dman who they couldn't re-sign. The Hawks lose because Bowman mistakenly thought the Hawks still had a contention window when they certainly did not. So the futures sent to the Jackets ended up not panning out at all and Jones hasn't kept the Hawks out of the gutter let alone made them a regular playoff team.

The Hawks will probably lose an upcoming Jones to Dallas deal as well because they're the ones now giving up the best player and getting a likely futures-based package. They'll get the benefit of not having his cap hit on the books when he declines in the next few years however.
It's not really over for either team. There's rumors Jones is being shopped and the Jackets got a 1st, 2nd, 3rd, 4th and a borderline NHL ready prospect in Hunt. And while Sillinger may not be a top line player, he's played his role well this year. He's just a case of a role player whose more than likely not gonna be someone you want to play above that role for very long.

It's gonna be a few more seasons until this truly shapes up.
 
Iginla to Pittsburgh. Seemed to work out bad for the teams and Iggy.

Flames got a shitty return for the face of the franchise in a late first who never amounted to anything and spare parts. Iginla lost out on a trip to the finals against the Bruins who he was almost traded to while never quite finding a fit in Pittsburgh and walking as a UFA.

Iginla was past his prime. He had decent numbers with Pittsburgh, who almost certainly knew he was a rental. When was the last time a 35+ year old player brought back a huge return? A 1st and a couple of prospects was the expected return for an older player who was an upcoming UFA. There were lots of emotions attached to the deal, but this wasn't really even a blockbuster. It's pretty standard fare now for vets to move around at the end of their careers.
 
I'm scratching my head as to who won the Kotalik + Regehr + 2nd for Byron + Butler trade or if both teams technically lost.

The 2nd turned into McCabe
Regehr flipped for two seconds to LA

The two seconds reacquired by LA with Parker + McNabb for Fasching + Deslauriers
 
I guess if one takes the PLD deal with Roslovic going the other way as part of it, the pieces from LA are tied back to it. But that still seems more from the Laine value than the Roslovic value. Other than that, I don't think there is much of tie left to the Jets out of all that -- Lemieux went for Hayes who went for a 5th that didn't sign. Myers left in free agency. Armia and Mason got shipped out as budget moves with draft picks for a guy who hasn't been in NA in years. Chisholm, who they picked with the pick from dealing Stafford to the Bruins went as a waiver claim to the Wild. I guess including Roslovic gets PLD and that means he's part of the Iafallo/Vilardi/Kupari/Freij return?

Murray wanted the Kings' style of punish defense and instead he got Temu Drew Doughty in Bogosian and a bunch of bad publicity with EKane who he wanted to ride shotgun for McDavid. In the end they got a badly broken defenseman and moved on from Kane when his off-ice stuff in Buffalo got to be too much.

The Sabres have Stiven Sardarian left on their reserve list drilling down to what they got (the pick for Kane went in the Montour deal, the pick for Sardarian they got back when they sold low on Montour). Ultimately kind of meh.
I don't really count the Laine/PLD trade considering they were pretty much traded for each other and the 3rd rounder was pretty much for Roslovic. I would say Laine turned into Iafallo, Vilardi and Kupari.
 

In the summer of 2008, Andrej Meszaros was an RFA after three productive seasons in Ottawa. Sens were up against the cap and didn't have the space to meet Meszaros' asking price.

Meanwhile Tampa Bay had new ownership fresh off of drafting Steven Stamkos. After trading away Dan Boyle, they wanted to get a young established defenseman who could be a cornerstone with Stamkos. So they decided to target Meszaros.

The rumor was that Tampa and Meszaros' agent had agreed to terms but they couldn't sign an offer sheet because Tampa had previously traded its 2009 3rd rounder which was a required part of the compensation. Allegedly Tampa tried to get it back from Pittsburgh, but Ray Shero thought he was doing the honorable thing by not trading it back and being an enabler.

Ottawa was a season removed from a SCF appearance so they understandably thought they were still a contender. So instead of just accepting Tampa's 2009 1st and 2nd via trade, they wanted an NHL D to replace Meszaros. Right before training camp started, Ottawa agreed to trade Meszaros to Tampa for Filip Kuba and San Jose's 2009 1st.

Tampa remained in the basement as Meszaros' offense would dry up. After a couple seasons, newly appointed GM Steve Yzerman would trade him to Philadelphia for a 2nd round pick.

Meanwhile Ottawa quickly dropped from contender status and would miss the playoffs. Kuba seemingly played decently but he was already in his early 30's when he was traded. Sens GM Bryan Murray would deal San Jose's 2009 1st for Mike Comrie and Chris Campoli.

Had they accepted Tampa's 2009 1st, Ottawa could have had Victor Hedman. That Tampa ownership lucked out by its own lack of foresight; They'd end up selling the team after just two years. I can't help but notice that bad owners seem to be a common thread in these bad trades.
The sens and lightning were also the two best drafting teams from 2008-2011. But just imagine if the Sens got their pick in 2009. Would have been a legendary 4 year draft period for the Sens.
 
Generally who gets the best player in a trade ends up winning the trade. So Columbus loses by trading a top-pairing Dman who they couldn't re-sign. The Hawks lose because Bowman mistakenly thought the Hawks still had a contention window when they certainly did not. So the futures sent to the Jackets ended up not panning out at all and Jones hasn't kept the Hawks out of the gutter let alone made them a regular playoff team.

The Hawks will probably lose an upcoming Jones to Dallas deal as well because they're the ones now giving up the best player and getting a likely futures-based package. They'll get the benefit of not having his cap hit on the books when he declines in the next few years however.
im of the mind you cant lose a trade if you had no chance of re-signing the player. Trading for junk is better than losing the player for nothing in UFA.

That said, Chicago wins by default, unfortunate situation for teams in that position where you had to eat a shit sandwich on a trade like that. Plus Chicago could still get something worthwhile for trading Jones, probably nothing that will help the rebuild, but its still something.
 
im of the mind you cant lose a trade if you had no chance of re-signing the player. Trading for junk is better than losing the player for nothing in UFA.

That said, Chicago wins by default, unfortunate situation for teams in that position where you had to eat a shit sandwich on a trade like that. Plus Chicago could still get something worthwhile for trading Jones, probably nothing that will help the rebuild, but its still something.
They didn’t become a better team after the trade. That may be an oversimplification but they lost nonetheless.

I think it just goes to show how overrated draft picks can be at the end of the day. The Hawks traded away a #6, #8 (Boqvist), and #12 pick for Jones and Nolan Allan. Allan may end up being the best player compared to Sillinger, Jiricek, and Boqvist (who he likely is already better than). Jones is obviously the most effective of the bunch.
 
I guess some of the young players (including the assets returned in the Jiricek trade) may yet prove worth… but at a glance, the trade of Seth Jones and the picks that became Nolan Allan and Dominic James… for Adam Boqvist and the picks that became Cole Sillinger, David Jiricek, and Aleksei Heimosalmi … seemed like a whole more more blockbuster value on both sides at the time than it does today.
Seth Jones has been better than expected for Chicago, although the contract is still not good. Doesn't fit the timeline.
 
They didn’t become a better team after the trade. That may be an oversimplification but they lost nonetheless.

I think it just goes to show how overrated draft picks can be at the end of the day. The Hawks traded away a #6, #8 (Boqvist), and #12 pick for Jones and Nolan Allan. Allan may end up being the best player compared to Sillinger, Jiricek, and Boqvist (who he likely is already better than). Jones is obviously the most effective of the bunch.
you are never going to be better after trading a superstar for futures. Thats why i dont view it as a win/loss situation for columbus because they had no choice but to make the trade, the player forced their hands and getting something back is better than not getting anything and walking at UFA.

I dont think these types of trades can be viewed with blockbusters as a win/loss situation like other trades.
 

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