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Carolina's Jake Guentzel
Carolina's Jake GuentzelJosh Lavallee/NHLI via Getty Images

Trades Haunting NHL Teams This Offseason

Joe YerdonMay 14, 2024

The beauty of making a trade is that judgments on them are often best left until later. That goes against how we like to make instant calls about who won and who lost, but time has a funny way of proving things in the end.

Making a deal always comes with risks, whether it's mortgaging the future for gains right now or shaking things up in a way that alters the course of a franchise for years to come. It's not always that drastic, but the pangs of regret can lurk around if the trades don't turn out the with the intended outcome.

It's the regrets we're locked in. The general managers who made the trades won't say they've got any regrets about the deals, but the end results have left some questions and concerns to be addressed now.

We're going to take a look at a handful of trades that may leave teams rueful over their decisions.

Los Angeles Kings and the Pierre-Luc Dubois Situation

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EDMONTON, AB - APRIL 24: Los Angeles Kings Center Pierre-Luc Dubois (80) heads in for a check in the second period of game two of the Western Conference First Round Edmonton Oilers game versus the Los Angeles Kings on April 24, 2024 at Rogers Place in Edmonton, AB. (Photo by Curtis Comeau/Icon Sportswire via Getty Images)
EDMONTON, AB - APRIL 24: Los Angeles Kings Center Pierre-Luc Dubois (80) heads in for a check in the second period of game two of the Western Conference First Round Edmonton Oilers game versus the Los Angeles Kings on April 24, 2024 at Rogers Place in Edmonton, AB. (Photo by Curtis Comeau/Icon Sportswire via Getty Images)

Trade: Los Angeles Kings acquire Pierre-Luc Dubois from Winnipeg Jets for Gabriel Vilardi, Alex Iafallo, Rasmus Kupari, 2024 2nd-Round pick

Few players in the NHL have as conflicting a reputation as Pierre-Luc Dubois.

In his previous stops in Columbus and Winnipeg, there were questions about just how good he is, how good he can be and where he ultimately wanted to play. He's had 60-or-more points in a season three times, but he's yet to crack the 30-goal barrier. He was the third overall pick in 2016, and anyone taken that high has sky-high expectations to begin with.

After the Kings gave up two young players and an established veteran along with a top-60 draft pick to land Dubois and signed him to an eight-year, $68 million extension, the bar was raised even more for him to hit the next level of his game.

Instead, the 25-year-old scored 16 goals and had 40 points, which led people to wonder if the Kings would buy out Dubois this summer after one year of his extension. That would've led to L.A. being punished for 14 years against the cap if it did that.

Fortunately, the Kings are not going to buy him out and will try to figure out the best way to make use of him. That may mean moving him to the wing even though they added him to be a top-six center. But adding Dubois and subtracting key role player Alex Iafallo as well as an excellent (but often injured) Gabriel Vilardi, it's messy.

After losing to the Edmonton Oilers in the first round of the playoffs for the third straight year and getting one goal in five games from Dubois, they'd better hope they get it figured out fast.

Pittsburgh Penguins May Rue Dealing Jake Guentzel

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ELMONT, NEW YORK - APRIL 25: Jake Guentzel #59 of the Carolina Hurricanes watches the closing seconds of the first period against the New York Islanders in Game Three of the First Round of the 2024 Stanley Cup Playoffs at UBS Arena on April 25, 2024 in Elmont, New York.  (Photo by Bruce Bennett/Getty Images)
ELMONT, NEW YORK - APRIL 25: Jake Guentzel #59 of the Carolina Hurricanes watches the closing seconds of the first period against the New York Islanders in Game Three of the First Round of the 2024 Stanley Cup Playoffs at UBS Arena on April 25, 2024 in Elmont, New York. (Photo by Bruce Bennett/Getty Images)

Trade: Pittsburgh Penguins trade Jake Guentzel and Ty Smith to the Carolina Hurricanes for Michael Bunting, Ville Koivunen, Vasily Ponomarev, Cruz Lucius and a conditional 2024 first-round pick.

If you've been watching the playoffs at all and seen how Jake Guentzel has provided the Hurricanes with an immediate boost, it probably came as no surprise.

After all, the 29-year-old has been one of the most productive wingers in the NHL, and doing so playing next to Sidney Crosby in Pittsburgh will earn anyone a lot of attention.

However, with Guentzel slated to become an unrestricted free agent this summer and the Penguins in a tricky position caught between keeping the dream alive and rebuilding on the fly, they traded him and are hoping they can re-sign him this summer.

After seeing how well he has done in Carolina, though, and knowing there will be plenty of other teams around the league with a lot more money under the cap to spend than perhaps the Penguins can offer, not to mention that the Hurricanes might want to keep him themselves, giving up control of Guentzel may wind up being a huge mistake.

Guentzel loves Pittsburgh and he was deeply moved by the fans' response to him when he went back to play there with Carolina, but anything can happen when anyone and everyone can reach out and make an offer.

And if the Penguins want to try to get back to the playoffs next season, having Guentzel would be preferable to not having him.

Ottawa Senators and the Alex DeBrincat Trades

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MONTREAL, CANADA - APRIL 16:  Alex DeBrincat #93 of the Detroit Red Wings skates during the second period against the Montreal Canadiens at the Bell Centre on April 16, 2024 in Montreal, Quebec, Canada.  The Detroit Red Wings defeated the Montreal Canadiens 5-4 in a shootout.  (Photo by Minas Panagiotakis/Getty Images)
MONTREAL, CANADA - APRIL 16: Alex DeBrincat #93 of the Detroit Red Wings skates during the second period against the Montreal Canadiens at the Bell Centre on April 16, 2024 in Montreal, Quebec, Canada. The Detroit Red Wings defeated the Montreal Canadiens 5-4 in a shootout. (Photo by Minas Panagiotakis/Getty Images)

Trade in 2022: Chicago Blackhawks trade Alex DeBrincat to the Ottawa Senators for a 2022 1st-Round pick, 2022 2nd-Round pick and a 2024 3rd-Round pick

Trade in 2023: Ottawa Senators trade Alex DeBrincat to the Detroit Red Wings for Dominik Kubalik, Donovan Sebrango and a conditional 2024 1st-Round pick

The Senators dealing away Alex DeBrincat was a losing move no matter what.

He was a restricted free agent and seeking a juicy new contract, but the Senators were in a messy spot. The team was being sold, they had salary-cap issues and there was immense pressure for them to get back to the playoffs sooner than later despite all of those things going on.

Ottawa did as well as they could, and getting a first-round pick out of the trade was a good thing. Of course, they dealt him to Detroit. The same Detroit Red Wings they have to compete with in the division to get to the playoffs and they got the best player in the trade.

The Senators haven't had a first-round pick since 2021, and they'll have at least two now at the 2024 draft (barring other trades). The pick they got from Detroit in the trade originally belonged to the Boston Bruins. The Red Wings got that pick from Boston when they traded Tyler Bertuzzi to the Bruins a year ago. That means the pick is late in the first round of a draft that's not overwhelmingly loaded with high-end talent.

Of course, they had to get a first in this trade considering they gave up a first in 2022 to get him from Chicago. That pick was seventh overall.

But with Ottawa in a "get to the playoffs now" mode, trading DeBrincat diametrically opposed that line of thinking. And while they've got a lot of good players up front, wouldn't they be better off figuring out how to keep DeBrincat as opposed to giving him to a direct competitor?

Fortunately for Ottawa, Detroit hasn't gotten over the hump itself, which saves them some amount of embarrassment, but it's a fine line to straddle.

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Tampa Bay Lightning and Tanner Jeannot

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TAMPA, FL - APRIL 17: Tanner Jeannot #84 of the Tampa Bay Lightning against the Toronto Maple Leafs during the first period at Amalie Arena on April 17, 2024 in Tampa, Florida. (Photo by Mark LoMoglio/NHLI via Getty Images)
TAMPA, FL - APRIL 17: Tanner Jeannot #84 of the Tampa Bay Lightning against the Toronto Maple Leafs during the first period at Amalie Arena on April 17, 2024 in Tampa, Florida. (Photo by Mark LoMoglio/NHLI via Getty Images)

Trade: Nashville Predators trade Tanner Jeannot to the Tampa Bay Lightning for Cal Foote, a conditional 2025 first-round pick, a 2024 second-round pick and a third, fourth, and fifth-round pick in the 2023 draft.

In a vacuum, the logic behind the Lightning acquiring Tanner Jeannot made sense.

Tampa Bay is in a "win now" mode because it's a playoff team and recently won back-to-back Stanley Cups. It has a load of high-end talent either in their primes or on the back end of it, and it felt it needed a player who plays physically and can provide offense as well.

The season before he was traded, Jeannot had a breakout year with 24 goals and 41 points to go along with his 130 penalty minutes. That kind of profile offered the best of both worlds for what the Lightning felt they needed come playoff time. But in his final season with Nashville before being traded he had five goals and 14 points and the Lightning gave up five draft picks and a depth player to get him.

Giving up three mid-draft picks right away wasn't going to hurt the Lightning. But with the core getting older, Steven Stamkos potentially headed to free agency this summer, and the prospect base thinning out the Bolts are going to need to start restocking the pipeline.

Losing a top-60 pick this year because of the trade and its first-round pick next year, the timing works against Tampa Bay when it comes to self-sustaining from within. Giving up draft picks to get offensive producers like Brandon Hagel is fine, but Jeannot has eight goals and 18 points along with 97 penalty minutes in 75 games with the Lightning.

GM Julien Brise Bois knew what he was signing up for in making that trade, but living with it may prove more uncomfortable.

Jakob Chychrun and the Ottawa Senators

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OTTAWA, CANADA - MARCH 24:  Jakob Chychrun #6 of the Ottawa Senators shoots the puck against the Edmonton Oilers at Canadian Tire Centre on March 24, 2024 in Ottawa, Ontario, Canada.  (Photo by André Ringuette/NHLI via Getty Images)
OTTAWA, CANADA - MARCH 24: Jakob Chychrun #6 of the Ottawa Senators shoots the puck against the Edmonton Oilers at Canadian Tire Centre on March 24, 2024 in Ottawa, Ontario, Canada. (Photo by André Ringuette/NHLI via Getty Images)

Trade: Arizona Coyotes trade Jakob Chychrun to the Ottawa Senators for a conditional 2023 1st-Round pick, a conditional 2024 2nd-Round pick and a 2026 2nd-Round pick

One of the reasons why the Ottawa Senators haven't had a first-round pick since 2021 is because they've pushed hard to get back to the playoffs by dealing them away.

Their 2022 first went to Chicago to acquire Alex DeBrincat, and their 2023 pick went to the Coyotes to add Jakob Chychrun.

Chychrun was one of the most hotly pursued trade targets in 2023 because he's a young phenom and it offered the acquiring team the first crack at signing him to a long-term extension when his contract ends in 2025. Although he will be an unrestricted free agent, whoever he is playing for can offer him a max-length contract for eight years.

When this season ended without a playoff appearance yet again, Chychrun sounded rather non-committal about whether he wanted to sign an extension in Ottawa. After all, with all the turmoil that's gone on in Canada's capital city, it's understandable. But with solid ownership in place you'd think that would make it a little more appealing to stay there.

But if Chychrun's seeming indifference about staying in Ottawa is how he really feels, the Senators are going to have to strongly consider trading him the same way they dealt DeBrincat. If they do, the least they can do is not send him to a team within the division.

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