The Red Wings have made numerous trades in their existence. And I would say that a majority of them have been good or, at the very least, not overtly bad.
However, there are more than a few trades that most people would consider to be bad, or even horrible! And that's what I'm here to talk about today.
It's essential to note that when going through these, most trades are not made to "swindle" the other team. While it's true that you try to get the best price possible for a player or a draft pick, you also don't want to gain a reputation around the league of lowballing and swindling other general managers.
When making a trade, you want to do your best to make a deal that ultimately gives both sides what they're looking for. Sometimes they work out in your team's favor, and other times it doesn't. Those kinds of things happen in professional sports, but I'm here to shine a spotlight on the bad ones.
Walman to San Jose was the worst trade in the Yzerman Era
As usual, we're gonna start out with the obvious and over-talked about example of this topic. Yes, the Walman trade was quite possibly the worst move in the Yzerman era, and we may never know why he made the move.
Some speculate he was a locker room cancer, others say it's because he was because he didn't take his injury recovery seriously. The most likely answer was that it was simply a cap dump.
For those of you who are somehow unaware, on June 25, 2024, the Red Wings traded second-round defense prospect Andrew Gibson to the Nashville Predators for a second-round pick and Jesse Kiiskinen.
Yzerman then flipped that second round pick and attached it with Walman and sent them both to San Jose for future considerations. A deal that still has fans and analysts scratching their heads to this day.
The move was made even more perplexing when you take into account that San Jose was able to get a first round pick for him during the 2024-25 trade deadline, and he performed well with San Jose and in Edmonton during the playoffs.
Regardless of the reasons, this trade will be looked at as quite possibly the biggest blemish on Yzerman's record as Red Wings GM, and we'll never know the real reason why it took place.
Kyle Quincy was not worth it...at all
There is no shortage of horrible moves during Ken Holland's "scorched-earth" tactics to keep the Red Wings' playoff streak alive. A series of signings and trades play a major part in why the Red Wings' current rebuild has been taking so long. Among them is the re-acquisition of Kyle Quincy in 2012 for a first-round pick and Sebastian Piche.
At the time, there was some logic in the deal. Was he worth a first round pick? Probably not, but he did have a few solid scoring years with LA and Colorado before the deal, so it made sense to bring him back into the organization.
Unfortunately, he collapsed after being traded and ended up getting extended, scoring a total of 16 points in 118 games while also averaging 19-20 minutes a night from 2012-2014. That was good enough for good ole Kenny H to not only extend him another two seasons, but also give him a $470,000 raise. During this extension, he scored 29 points in 120 games.
When it comes to Quincy, it's not just the fact that the Wings gave up a first round pick for him to be nothing more than a fourth or fifth defenseman, at best. But also that first-round pick went on to become Andrei Vasilevskiy, who became one of, if not the best, goalies in the NHL.
We don't know if the Red Wings would've taken Vasilevskiy had they kept the pick. But it doesn't make the trade look any better.
The Adam Oates trade may be the worst trade in Red Wings history and nobody talks about it
68I dove into the history books for this one, and it may just be the worst trade in Red Wings history, but few remember it, and even fewer talk about it. If you don't know who Adam Oates came into the NHL with the Red Wings in 1985-86 for 38 games, where he recorded nine goals and 20 points before going down to the AHL to play for the then Adirondack Red Wings, where he helped lead them to a Calder Cup.
In total, he scored 199 points in 246 games with the Red Wings before then general manager Jim Devellano traded him with Paul MacLean to the St. Louis Blues for Tony McKegney and Bernie Federko.
Looking at the history of all of these players, on the surface, it looked as if the Red Wings won this deal. Federko was a consistent 80-90-plus point player with four 100-plus point seasons under his belt, and McKegney was a 40-60 point veteran.
While Oates was a young gun with similar scoring to McKegney and MacLean was a good top-six veteran with good scoring. It's not until you find that after the trade, everybody except for Oates either fell off or retired.
Federko was already on a downturn when he came to the Red Wings and then retired after the 1989-1990 season, scoring 57 points in 73 games with the Wings. While McKegney only lasted 14 games with the Red Wings, scoring three points before being traded to the Quebec Nordiques.
While MacLean retired one season later, Adam Oates went on to be a superstar immediately after being traded, putting up two 100-plus point seasons in 1989-90 and 1990-91. He followed that up with two seasons over a point per game with the Boston Bruins and St. Louis Blues before two more 100-plus point seasons in 1992-93 and 1993-94 with the Bruins.
In total, he would play in the NHL for 19 seasons, retiring in 2004 with the Edmonton Oilers, finishing his Career with 1420 points in 1337 career games.
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