Jets Trade Deadline Preview: Pressure on Cheveldayoff to wheel and deal

WINNIPEG — Winnipeg Jets general manager Kevin Cheveldayoff is approaching the most consequential trade deadline of his 14-year tenure.

The NHL’s second-longest serving GM faces pressure from above and below. 

Another first-round exit would be devastating for both ownership and the players. 

True North Sports and Entertainment needs a long playoff run.

Despite sitting atop the standings all year, Winnipeg is only averaging 14,154 fans per game — 1071 short of selling out the NHL’s smallest arena —  and remains thousands of season ticket holders short of their intended 13,000 mark. 

Failing to reach the second round for a third straight year could have serious implications on the organization’s ability to replenish its season-ticket base. And with the salary cap about to rise, every bit of revenue counts for the NHL’s smallest market.

The players need a long playoff run. 

Winnipeg’s core has been through the wringer over the last two years, where strong regular seasons were followed by swift postseason exits. Most of their core pieces have remained since the 2018 Western Conference Finals run, and the disappointing years thereafter. In spite of that, Cheveldayoff was able to sell Mark Scheifele and Connor Hellebuyck on the prospect of Winnipeg being a perennial contender when he inked them to identical eight-year extensions. 

The same conversation will surely be had with Kyle Connor, who is eligible to sign an extension on July 1. And if the Jets have any chance at re-signing Nikolaj Ehlers at the 11th hour, they’ll need to convince him, too, that this team is a legitimate contender. 

“We trust Chevy,” Connor told reporters on Monday. “And he’s going to do the best job he can to make this team a Stanley Cup champion.”

That pressure on Cheveldayoff — from both ownership and his players — aligns with what might be this team’s best shot to win a Stanley Cup. They’ve got a boatload of cap space and a Hart-calibre goalie highlighting a core group of players who are playing the best hockey of their career. 

That’s why it would be downright shocking if Cheveldayoff isn’t wheeling and dealing from now until Friday. 

Projected deadline day cap space: $12,403,389, according to PuckPedia.

Contracts: 41/50

Cap space committed to 2024-25: $84,473,691 (committed to 25 players)

DRAFT PICKS

NEEDS

Second-line centre. Two defencemen. And a faceoff specialist. 

An upgrade below Mark Scheifele on the depth chart is Winnipeg’s most pressing need upfront.

Vladislav Namestnikov has been fine between Nikolaj Ehlers and Cole Perfetti, but the Jets need an upgrade for the same reasons they acquired Sean Monahan last year. Size and scoring prowess down the middle are coveted come playoff time. 

On the back end, there are a couple of players miscast in their roles. 

Dylan DeMelo has always complemented Morrissey well, but he doesn’t profile as a top-pairing, right-handed defenceman on a cup contender. The Jets need someone that possesses similar attributes to DeMelo — solid defensive instincts and stickwork — but with a bit more size. Not to take away from the Jets’ blue line this year, but they’re one of the league’s smallest, and we saw how they struggled to clear net-front traffic against Colorado. Winnipeg could also benefit from adding a seasoned left-shot defenceman to round out their third pair. They need an insurance policy in the event of Morrissey or Dylan Samberg getting banged up. Right now, Logan Stanley is the next man up. 

And the cherry on top would be faceoff help. Not only do the Jets rank 24th in faceoff win percentage, but they’re also 28th in penalty kill draws (42 per cent). 

POTENTIAL TARGETS

Brock Nelson, C, New York Islanders: The price for Nelson, an expiring UFA, will be high — given the scarcity of high-impact rentals — but he checks off every box for Winnipeg. With 20 goals in 61 games, Nelson is on pace for 27 goals — a slight dip from the past three years, where he registered 34, 36 and 37-goal seasons — but keep in mind, the Isles are one of the NHL’s worst offensive teams. Nelson’s ability to generate net-front offense and leverage his six-foot-four frame to extend plays are exactly what the Jets need on their second line. Plus, he’s a trusted penalty killer who is also winning a career-high 52.8 per cent of his faceoffs this year.

Josh Norris, C, Ottawa Senators: This would be the type of home run swing that, if all goes well, could end the Jets’ annual search for a second-line centre. Since inking an eight-year, $63.6 million contract following a 35-goal campaign in 2021-22, Norris has been derailed by injuries and has recorded just 37 goals and 64 points in his last 110 games. Norris has been treading upward this season, scoring 19 goals through his first 52 games — putting him on pace for 27 goals. The 25-year-old is a reliable, two-way center who competes on the forecheck and possesses a high-end shot. 

Rasmus Ristolainen, D, Philadelphia Flyers: Under John Tortorella, the 30-year-old has evolved into a second-pairing defenceman who can be trusted on the penalty kill. Ristolainen is physical, can kill plays and is quite mobile for a six-foot-four defender. Players like that are a hot commodity this time of year, especially when they have two years remaining on their contract ($5.1 million). Several league sources told Sportsnet.ca that the Jets have long been intrigued by Ristolainen, dating back to his days with the Buffalo Sabres. Flyers GM Danny Briere is also reportedly in no rush to trade Ristolainen — it will take an enticing package to pry him out of Philly. 

Carson Soucy, D, Vancouver Canucks: Soucy makes sense for a lot of reasons. The six-foot-5 defender can play on both the left and right side — he could slot in either alongside Morrissey or replace Stanley — and he’s an excellent defender, with a knack for disrupting opposing team’s zone entries. Soucy is one of several players struggling in Vancouver this year and his role has become redundant since Marcus Pettersson arrived. Soucy possesses a heavy shot — he scored 10 goals with Seattle in 202-22 — and he’s got 38 games of playoff experience under his belt. 

Jean-Gabriel Pageau, C, New York Islanders: Pageau fits the bill for what the Jets need to round out their bottom-six. A highly dependable faceoff ace, Pageau has won 59.6 percent of his draws this year. He also sports a 61 percent faceoff win percentage on the penalty kill and plays a hard, north-south game. The 32-year-old carries a $5 million AAV through next season and while there’s a value to his cost certainty, Cheveldayoff may need some salary retention to justify acquiring such an expensive fourth-line centre. The thought of Pageau and Alex Iafallo on the Jets’ fourth line is tempting — that’d be a matchup nightmare for opponents. He’s got 86 games of playoff experience, too.

ASSETS TO TRADE

2025 first-round pick: I’d be shocked if the Jets still have this pick when the deadline passes. Given that it’s going to be a late pick, in a weaker draft, it’s basically a high second-round pick. 

2026 first-round pick: The 2026 draft is supposedly much stronger than this year’s, but assuming the Jets are confident they’ll be near the top of the standings next year, they shouldn’t balk at moving this pick if the right deal comes around.

Elias Salomonsson, D, Manitoba Moose (AHL): Salomonsson is essentially untouchable within the Jets’ prospect pool. That said, if an opportunity to acquire a cost-controlled, high-impact player asset, Cheveldayoff shouldn’t entirely rule out moving him. The 20-year-old Swede is having an excellent first year pro with the Moose, logging north of 20 minutes per night and playing on both the power play and penalty kill. Salomonsson is a two-way defenceman who utilizes his six-foot-two frame to play with a bit of a bite. The 2022 second-round pick is raw — he’ll likely need another year in the AHL after this season — but he has all the tools to be a solid top-four defenceman. 

Brayden Yager, C, Lethbridge Hurricanes (WHL): Yager has been an encouraging addition to the Jets’ prospect pool since coming over in the Rutger McGroarty trade. The 2023 first-round pick has recorded 74 points in 48 WHL games this year, all the while displaying a strong two-way game. Contrary to the player he was traded for, the Saskatoon native is excited by the opportunity to play for Winnipeg — which could make Cheveldayoff hesitant to move him, even for a strong return.

Brad Lambert, F, Manitoba Moose (AHL): Lambert’s pedestrian stat line this year — 25 points in 43 AHL games — is largely a byproduct of Manitoba’s struggles. The 21-year-old, one year removed from recording 55 points in 64 games and being named an AHL All-Star, possesses game-changing skating ability and a quick release on his wrist shot. If Ehlers walks this summer, Lambert, stylistically, seems like a natural top-six replacement. That said, don’t rule out Lambert being moved if it nets the Jets a cost-controlled top-six piece. 

Colby Barlow, LW, Oshawa Generals (OHL): Barlow had a disappointing training camp showing this past fall and he hasn’t dominated the OHL the way you’d expect him to. That said, the 2023 first-round pick still possesses a game-breaking shot, and while his game is still raw — he needs to improve his play off the puck — several NHL teams are still intrigued by his upside.

Kieron Walton, C, Sudbury Wolves (OHL): Walton, a 2024 sixth-round pick, is Winnipeg’s fastest rising prospect. The six-foot-six centre has been a human highlight reel with Sudbury, recording 34 goals and 82 points in 56 games. His toolbox is a rarity — players that big usually don’t have that good of a feel for the puck. 

Kevin He, Niagara IceDogs (OHL): He, a fourth-round pick, was another mid-round gem from the 2024 draft. After a strong training camp showing, the 18-year-old has gone on to record 31 goals and 68 points in 54 games. The six-foot winger has an intriguing skillset, highlighted by a high-end motor and a nose for the net.

OTHER CONSIDERATIONS:

Could we see the Jets add draft picks or prospects? Given that the Jets are expected to be aggressive yet again — after trading a first, second and fourth for Sean Monahan, Tyler Toffoli and Colin Miller last year — Winnipeg will soon have a pretty barren cupboard. 

If the Jets have some extra cap space after making their additions, they’d be wise to act as a third-party broker for cap-strapped teams and retain salary in exchange for picks or prospects. It’s a tactic we’ve seen several organizations — contenders, bubble teams and basement-dwellers — utilize recently. On Tuesday, New Jersey retained 25 percent of Trent Frederic’s salary in exchange for the signing rights of a prospect, Shane Lachance. 

For Winnipeg to continue running its franchise the way they have — by building through the draft and making shrewd trades — they’ll need to add more ammo. 

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