What past trade deadlines tell us about how Jets GM Cheveldayoff may act

We all heard the jokes. Kevin can take the Chevel-Day-Off because he’ll just be sitting on his hands, anyway.

Yes, the Winnipeg Jets GM was sometimes accused of being something beyond patient when it came to making trades aimed at improving his club. But looking back on it — and you have to look back pretty far because Cheveldayoff has been on the job 12 years and is the third-longest tenured GM in the NHL — maybe it was more a case of biding his time while the Jets were developing rather than being reluctant to pull the trigger.

The Jets made the playoffs one time in their first six seasons back in Winnipeg and that year — 2014-15 — felt more like a one-off surge than a case of the team truly arriving. After all, they did miss the post-season again each of the next two years.

But in 2017-18, the Jets had a burgeoning young roster and were chugging through a year that ended with a franchise-best 114 points. It was time to act and Cheveldayoff put his 2018 first-round pick on the table to acquire Paul Stastny from the St. Louis Blues. The veteran forward was the perfect add to a young roster, with Stastny’s ability to play either centre or wing and his dependability in all three zones. Stastny was good for Winnipeg down the stretch and even better in the playoffs where he netted 15 points in 17 games as the Jets advanced all the way to the Western Conference final before being downed by the expansion team-of-destiny from Vegas.

Stastny walked as a free agent that summer, but that didn’t prevent Cheveldayoff from stepping up again at the 2019 trade deadline as he spent another first-round pick on a pending-UFA, this time centre Kevin Hayes of the New York Rangers. The move didn’t pay off the way it did with Stastny as the Jets were ousted in the first round by a St. Louis club that wound up claiming the Cup.

(Worth noting: Stastny, of course, wound up returning to the Jets via trade in 2020 while the first-rounder Winnipeg sent to the Rangers for Hayes also returned home because New York sent it back to the Jets that summer in the trade for Jacob Trouba. Winnipeg used the pick on blue liner Ville Heinola).

Regardless, nobody could accuse Cheveldayoff of inaction in 2018 or ’19 guiding teams he felt had a real shot at doing something.

Which brings us to this year.

Winnipeg has been one of the surprise stories of the season and stand as good a chance as anybody of earning home-ice advantage throughout the Western Conference playoffs. In all likelihood the Jets would be most inclined to make an add to the back end. While we can’t rule anything out, Winnipeg doesn’t seem like a probable landing spot for the likes of Jakob Chychrun or Erik Karlsson, two high-end defencemen with term left on their deals.

But re-visiting another recent deadline when the Jets were playoff-bound might be instructive here. In 2020, just weeks before the world broke in half thanks to the pandemic, Cheveldayoff added Dylan DeMelo from the Ottawa Senators for a third-round pick. DeMelo, of course, is still a valued member of the Jets blue line because he wound up inking a four-year deal to stick with the club. We all know the Jets like guys with term or players who might be open to staying because they don’t tend to be a top destination — to be charitable — in free agency.

It's too bad Chicago’s Jake McCabe basically has all of Canada on his no-trade list because, with a contract that runs through 2024-25, he might have been a nice fit.

There may not be a perfect parallel for the DeMelo swap, but Cheveldayoff can still get creative. What about old friend Tyler Myers? If Vancouver would swallow half of his remaining money, the Jets could get him for the rest of this season and next to play a supporting role on the D corps. If not that right-shot 33-year-old Canuck, how about another one in Luke Schenn? The proud prairie boy and pending-UFA could almost certainly be had and possibly retained as he looks to stick with a competitive club.

The bottom line: Cheveldayoff has been willing to put chips in the middle when he senses his team has a real shot. Given the lay of the Western Conference land and the fact the Jets have a goalie advantage on maybe everyone save Dallas, you could make a strong case this squad has as good a chance as any in the Jets 2.0 era to make a deep run.

Let’s see if the GM acts accordingly.