Trade Deadline Winners and Losers: Eastern Conference, somehow, gets even better

Let’s get this out of the way; the first winner of what we’ll call “trade deadline season 2023” was us, the ravenous, talk-trade-to-me hockey-consuming media and fans who can’t get enough of this stuff.

So the day itself was a dud. That’s more than fine when it’s preceded by two weeks of tantalizing moves.

Was a record-setting points pace enough for the Boston Bruins? No chance, as the B’s plugged holes big and small. You want two other title-starved Original Six teams going all in? The Blueshirts (almost 30 years without a Cup) and Buds (are we even counting anymore?) have you covered. On the other end of that equation, we saw the Chicago Blackhawks officially turning the page on a storied chapter by trading Patrick Kane to the Rangers, while St. Louis — though it never had a dynasty — did also break with its recent, ring-defined past by sending the MVP of their 2019 championship run, Ryan O’Reilly, to the Maple Leafs.

Maybe neither of those guys are in their prime any more, but Timo Meier and Jakob Chychrun sure are and, in a fairly remarkable twist, neither fetched the type of package we all expected for sellers San Jose and Arizona.

You can probably guess where you’ll find those players’ new teams, New Jersey and Ottawa, in this sorting of winners and losers.

Let’s just dive into it then, shall we, and see who’s smiling and who — at least at first blush — came out on the wrong end of a rollicking deadline season.


New York Rangers

Earlier this week I listened to an episode of The Rewatchables movie podcast that focused on the 2002 picture “Catch Me If You Can.” For the uninitiated, Leonardo DiCaprio plays a con man fond of reminding people that the reason everybody loses to the New York Yankees is because they’re too memorized by the Yanks’ beautiful pinstripes.

You know why teams might lose to the New York Rangers? Because so many fantastic players want to play there and nowhere else. After months of agonizing will he/won’t he, it was basically Broadway or bust for Patrick Kane. Because of that fact, New York GM Chris Drury didn’t even have to give up a guaranteed first-round pick to get Kane. He now joins Adam Fox and Artemi Panarin as guys who found paths to their preferred destination of Madison Square Garden.

How the team came to be is irrelevant; all that matters is what this club can do on the ice and when you combine Kane’s acquisition with the previous move to snag Vladimir Tarasenko from the Blues, you have a completely transformed top-six forward crew for a team that made the final four last year even with its offensive limitations.

It might be next-step time in New York.

New Jersey Devils

We arrive at the rub early here, because the first two teams listed as winners are on a first-round collision course, underscoring the fact that for all these bold moves made by Eastern Conference powers, they still have to figure a way through the excruciating math that only one of them can emerge a conference champ.

A first round ‘Battle of the Hudson’ would be spicy under any circumstances, but the fact the Rangers did what they did and the Devils went out and scooped up 26-year-old Timo Meier makes it all the more tasty. Meier feels like the perfect addition for the up-and-coming Devils because there’s every chance the Swiss winger — a pending restricted free agent — will stick around with his countryman Nico Hischier and help this Devils squad be a contender for years to come.

Ottawa Senators

At the 2022 NHL Draft, Sens GM Pierre Dorion made a roundly lauded move by acquiring Alex DeBrincat — a sniper with some measure of team control — for three draft picks. Well, Dorion one-upped himself less than a year later by getting 24-year-old stud defenceman Jakob Chychrun from the Coyotes for a 2023 first, and (in all likelihood, depending on some conditions) two second-rounders. That’s about one first-rounder and one ‘A’ prospect less than we heard Arizona was demanding for the roughly 15 months Chychrun was known to be on the block.

The left-shot, six-foot-two defender is under contract for two more years past this one at an extremely palatable cap hit of $4.6 million.

Dorion is becoming a “winners” staple in these pieces.

Very Happy

Toronto Maple Leafs

Cross a GM on an expiring deal with an ultra-talented team that is 0-for-6 in first-round series and you get the all-in Toronto Maple Leafs. Kyle Dubas’ moves are bold and intuitive, as he added Ryan O’Reilly to the top-six forward crew and a slew of defenceman that bring either toughness and stability (Luke Schenn, Jake McCabe) or pure offence (Erik Gustavsson). Sam Lafferty and Noel Acciari are real boosts to the bottom two lines.

It must be noted Dubas did this without surrendering Matthew Knies or Nick Robertson, two forwards who could be helping the Leafs in a meaningful way by this time next year.

Washington, Nashville and St. Louis

Being honest with yourself is always a good thing and you have to admire the way these three teams leaned into selling when they didn’t necessarily have to. Young defenceman Rasmus Sandin was a nice pickup for the Caps, while Nashville is clearing embarking on a new path as Barry Trotz prepares to take over the controls from Day 1 GM David Poile.

St. Louis, meanwhile, now holds three first-rounders in the talent-rich 2023 draft.

Boston Bruins

Adding Dmitry Orlov and Garnet Hathaway seemed like the perfect, semi-soft touch for a team cruising toward a 135-point season. But with Taylor Hall injured and no timeline for his return, GM Don Sweeney swung again, picking up Tyler Bertuzzi from Detroit. Great stuff from a great team.

Edmonton Oilers

Mattias Ekholm may be on the back nine, but he’s still the sturdy type of top-four presence the Oilers have been after for a while. There’s no doubt he makes Edmonton better overall.

You Tell Me

Detroit Red Wings

On one hand, respect to GM Steve Yzerman for potentially selling high on Filip Hronek and for having the fortitude (not that there was any doubt with that guy) to move Tyler Bertuzzi before the pending-UFA had a chance to leave Detroit for nothing in the summer. It’s wonderful that Detroit has hung around the Eastern Conference playoff picture, but the odds the Wings actually emerge from the glob of teams gunning for those final two wild-card berths is pretty slim.

From that perspective, picking up two first-round picks is probably a shrewd move.

Still, anybody who saw Dylan Larkin choking up talking about how hard it was to say good-bye to Bertuzzi with these team — at least in the minds of its players — firmly in the battle for a playoff spot could justifiabley wonder if Yzerman took the right tack, especially moving Hronek — a player with some measure of team control left — during the middle of a career (or maybe breakout?) season.

Vancouver Canucks

If you’re a Canucks fan hoping for a bottom-up rebuild, it’s probably best to just make peace with the fact management doesn’t share your vision. Vancouver shipped the first-rounder it got from the Islanders in the Bo Horvat deal — the move that kicked off this whole deadline season just before the All-Star Game — to Detroit for Filip Hronek. Do we see the appeal? Sure. Hronek, as noted, is having a great year and 25-year-old, right-shot defenceman are typically in demand. But as the Canucks sell on other fronts, it’s just hard to square what the plan is here and how timelines line up for this team that is…rebuilding? Re-tooling? Re-shuffling? Re-ally confusing.

Carolina Hurricanes

The Canes didn’t necessarily have to make a big move, but with other Eastern powers loading up, you would have loved to seen Carolina get in there and make a splash.


San Jose Sharks

I’ve read more than one piece that cautions against rushing to judge a return package and that’s certainly good advice; our assessment of what San Jose received today could be very different 18 months from now.

Still, if you’re a Devils fan and you know you’re getting Meier — who does come with some measure of team control as a pending-RFA, albeit one with a crazy-high qualifying offer — you’re probably ready to bite down and give up the likes of an Alexander Holtz, maybe even Simon Nemec. Nope.

New Jersey sent a raft of players and picks to San Jose, but right now, it’s hard to identify a crown jewel among them. That’s not great for first-year Sharks GM Mike Grier as he slowly tries to restore the Sharks to their previous standing as a league power.

We all figured the Erik Karlsson trade would be a tough swap to make right now, so let’s see what Grier might come up with around the draft or ahead of free agency when teams have a little more cap flexibility to play with.

Arizona Coyotes

We all understand the Coyotes’ reluctance to retain salary on Jakob Chychrun, but man, how many offers would have topped what Ottawa gave up had Arizona swallowed a bit of money? Arizona’s stated goal is to build a stock pile of draft picks the likes of which the league has never seen and its well on its way to doing that. From the Coyotes perspective, maybe this has gone just fine, but from the outside looking in, it’s hard to slot them anywhere else but in the loser category after the Chychrun saga ended with such a fizzle.

Philadelphia Flyers

There’s no reason James van Riemsdyk, a depth scorer who can help your second power-play unit, and his expiring contract should still be on this team. Even a small missed opportunity is still a whiff.


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