What does Kevin Cheveldayoff have up his sleeve?

With just under a week to go before the NHL’s trade deadline, there’s still no clear indication about whether or not the general manager of the Winnipeg Jets is going to pull off a blockbuster deal, make a minor move to add depth or sell off a few pieces to bring back a couple of assets.

The Jets remain in the thick of the wild card chase in the Western Conference, sitting just a point behind the Arizona Coyotes and Calgary Flames, with 22 games remaining.

That’s a far cry from the secure position near the top of the Central Division standings the Jets enjoyed going into the past two trade deadlines.

How will that affect the Jets’ approach this time around?

“The approach really begins and essentially ends with: ‘Is there a right fit out there. Is there something that makes sense that we have the ability to do. That we have the wherewithal to do. That makes sense in fitting into the lineup and actually helping us and moving the needle,’” Cheveldayoff said last week. “That’s the approach, whether you’re in first place or the situation (we’re in) where you’re one point out of the equation right now. That’s (where) the evaluation process starts. You have the conversations with different teams and you try to put yourself in a situation where you’re in those conversations to know what the asking prices may be if there are fits out there.”

Since several teams are still trying to decide whether they’re going to be buying or selling, the asking price isn’t always available until the hours before the deadline actually arrives at 3 p.m. CT on Feb. 24.

“That’s a difficult thing because it changes, really, for a lot of teams, daily — based on injury, based on their injuries, based on their positions. Teams that may not be sellers may become sellers,” said Cheveldayoff. “Every situation is different so you’re trying to prepare for all of those things. But again, there has to be that right fit out there. You can’t just try to shoehorn something in. Over the last couple of years, we found some big moves that we felt could help us move the needle.

“We had to make some quick moves when we had some injuries, obviously to Josh (Morrissey) last year the night before the trade deadline, so you’re constantly evaluating what is out there, what the asking prices are, and do you have the assets to do it. It starts with: ‘Are there pieces out there that actually make sense for you?’”

With that in mind, let’s take a closer look at the five best trade deadline deals Cheveldayoff has made since becoming the Jets general manager in the summer of 2011:

(James Carey Lauder-USA TODAY Sports)

1. Feb. 26, 2018 — Jets acquire C Paul Stastny from St. Louis Blues for a 2018 first-round pick, the rights to LW prospect Erik Foley and a conditional fourth-round pick in 2020. The Blues also retained 50 percent of Stastny’s remaining salary.

To the outside world, this deal came entirely out of the blue, no pun intended.

The Jets’ interest in picking up a centre was well known, but the Blues were on the periphery of the playoff race and Stastny had a no-movement clause and had been an important contributor for quite some time, so few teams knew he was even available and he wasn’t on any of the trade boards that are prevalent at this time of the year.

Blues GM Doug Armstrong ultimately decided to move Stastny and made some significant alterations down the middle the following summer, trading for Ryan O’Reilly and signing free agent Tyler Bozak.

Safe to say that raising a banner and having a parade in the summer of 2019 allowed Armstrong to feel pretty good about the deal from his perspective.

For the Jets, this move was a grand slam on a number of levels.

The addition bolstered the Jets’ depth down the middle and Stastny fit in seamlessly, anchoring the second line with Patrik Laine and Nikolaj Ehlers and giving an already dangerous power play another weapon.

Stastny was a quiet leader and his playoff experience came in handy when the Jets entered the postseason.

That’s when Stastny was at his best. His most magical moments came in Game 7 of the Central Division final, when he had two goals and an assist, chasing Pekka Rinne from the game in the first period as the Jets eliminated the Nashville Predators.

Stastny’s willingness to waive his no-movement clause was also important for a franchise that still finds itself on numerous no-trade lists.

The Jets took a hard run at keeping Stastny in the fold and were a finalist to secure his services, but ultimately the veteran pivot signed a three-year deal with the Vegas Golden Knights.

2. Feb. 11, 2015 — Jets acquire defenceman Tyler Myers, right-winger Drew Stafford, right-winger Joel Armia, rights to left-winger Brendan Lemieux and a 2015 first-round pick (Jack Roslovic, 25th overall) for defenceman Zach Bogosian, left-winger Evander Kane and the rights to goalie Jason Kasdorf.

This was the first true blockbuster Cheveldayoff pulled off and it was a franchise-altering move.

Kane had asked to be dealt on numerous occasions and Cheveldayoff finally gave him his wish after the infamous tracksuit incident in Vancouver.

The Jets changed their personnel mix significantly and found an organization that was trying to do the same.

The move also altered the Jets’ identity to a degree, since both Kane and Bogosian fell under the fast-and-hard-to-play-against pillars.

Myers and Stafford were rejuvenated by the move and helped the Jets earn the final wild card berth in the Western Conference.

Stafford chose to re-sign with the Jets in the summer of 2015, so he wasn’t just a rental either.

Armia was mostly a third-liner and a valuable penalty killer who showed flashes of offensive brilliance during his time with the Jets.

He became a victim of the salary cap when the Jets moved him along with goalie Steve Mason to the Montreal Canadiens in the summer of 2018.

Lemieux brought an edge and was a shift disturber when he became an NHL regular and was a double-digit goal scorer before he was eventually moved in a separate trade-deadline deal.

Roslovic is into his third season with the Jets and has moved into a middle-six role this season as he’s already put up career highs in goals (12) and points (25), with 22 games left to go.

Oddly enough, Roslovic is the only player on the active roster, since Bogosian cleared waivers and was assigned to the Rochester Americans of the American Hockey League last week.

3. Feb. 25, 2016 — Jets acquire a 2016 first-rounder (which ended up being defenceman Logan Stanley) and forward Marko Dano from the Chicago Blackhawks for left-winger Andrew Ladd, defenceman Jay Harrison and left-winger Matt Fraser. The Jets retained 36 percent of Ladd’s remaining salary for the season.

This deal came on the day before the deadline and was inevitable after the Jets were unable to come to terms on an extension for Ladd, a pending UFA.

When Byfuglien inked his five-year extension on Feb. 8 of 2016, the trade rumours heated up and Ladd was eventually sent back to Chicago, where he was chasing another Stanley Cup.

Dano appeared in 82 games with the Jets over three seasons but never really made the impact that was expected of him.

The Jets’ original target in discussions for Ladd was forward Teuvo Teravainen, but the Blackhawks wouldn’t budge.

Teravainen was traded to the Carolina Hurricanes the following summer for draft picks and the Finnish forward has blossomed into a front-line player.

Stanley is into his second AHL season and remains a prospect, but he requires some additional seasoning before he’s ready to challenge for a full-time spot on the NHL roster.

(James Guillory-USA TODAY Sports)

4. Feb. 25, 2019 — Jets acquire centre Kevin Hayes from the New York Rangers for a 2019 first-rounder (which came back to the Jets in the deal for Jacob Trouba), left-winger Brendan Lemieux and a conditional fourth-round pick in 2022 (condition not met as Jets did not win the Stanley Cup)

For the second time in as many seasons, Cheveldayoff added a second-line centre, though this one didn’t make the same impact as Stastny.

Although the deal didn’t yield the same results, the decision-making process was sound.

With Patrik Laine and Kyle Connor in the final year of their entry-level contracts and the Jets spending most of the season at or near the top of the Central Division standings before a second-half swoon, adding a complementary piece was the right move.

Hayes was a two-way pivot who could kill penalties, is a playmaker and reached Game 7 of the Eastern Conference final with the New York Rangers, among the 30 playoff games on his resume before his arrival in Winnipeg.



Hayes never truly clicked with Laine and Ehlers and didn’t end up having nearly the same impact as Stastny, but some of that had to do with outside forces.

The what-if portion of this deal remains more tantalizing than the end result, and history would probably look at things much differently had Hayes scored to make it 3-0 in Game 5 against the St. Louis Blues rather than accidentally preventing his own deke from crossing the goal line as he was being tackled by Colton Parayko.

5. Feb. 25, 2019 — Jets acquire defenceman Nathan Beaulieu from the Buffalo Sabres for a sixth-round pick in 2019

The Jets lost defenceman Josh Morrissey to a shoulder injury on the night before the deadline last year, which precipitated a pair of moves to add depth on the blue line.

Bogdan Kiselevich was also acquired for a draft pick from the Florida Panthers, but he never actually suited up in a game for the Jets and returned to the Kontinental Hockey League this past summer.

Beaulieu went from being a frequent healthy scratch with the Sabres to jumping onto the Jets’ shutdown pairing with Jacob Trouba.

Talk about a change of scenery.

When Morrissey returned for the playoffs, Beaulieu was back in the press box, but the two sides decided to extend the relationship in the summer.

Since the Jets were a bit concerned about going to arbitration with Beaulieu, given his previous salary and experience level, they didn’t extend a qualifying offer to him but the two sides came to terms on a one-year deal on July 1.

Beaulieu has endured an injury-filled season, but he’s sparked his teammates with a couple of fights in recent weeks and delivered the game-winning goal in Sunday’s 3-2 victory over the Chicago Blackhawks (snapping a 59-game drought in the process).

(Top photo: Darcy Finley/NHLI via Getty Images)