On the eve of the final day before the NHL’s 2024 trade deadline, the Winnipeg Jets found themselves at a fork in the road.
Rewind to this time last year, and GM Kevin Cheveldayoff’s club was clinging to a wild-card spot, any path to meaningful playoff success running through a Western Conference juggernaut. They wound up unable to hurdle that barricade, bounced from the post-season in five games by the eventual Stanley Cup champions.
This time around, with deadline day looming, there was only hope and optimism in the halls of Canada Life Centre. The Jets had emerged as something of a juggernaut themselves, going toe-to-toe with Dallas for the Central Division crown, with those Stars and the Canucks, too, for the Western Conference throne.
Rick Bowness’s group was putting together something special, and Cheveldayoff rewarded their progress by swinging early, adding veteran centreman Sean Monahan to the mix early last month. The former Montreal Canadiens and Calgary Flames pivot fit like a dream from the jump.
Then came deadline week, and the inevitable Western Conference arms race.
In Colorado, Chris MacFarland brought in young standout centre Casey Middlestadt, depth winger Brandon Duhaime and defender Sean Walker, shoring up their already-elite depth for the home stretch. In Edmonton, Ken Holland added veteran Adam Henrique, along with depth forward Sam Carrick and blue-liner Troy Stecher. Dallas’s Jim Nill beefed up his club’s blue line too, winning the sweepstakes for rugged rearguard Chris Tanev.
Meanwhile, the defending champs wreaked havoc upon the trade market, Kelly McCrimmon adding standout Noah Hanifin to a blue line already stocked with gems, and tossing in talented forwards Tomas Hertl and Anthony Mantha, too, for good measure.
And there was Winnipeg, watching it all unfold around them, forced to decide how much belief they really have in this season, in this group.
“For most of my career, I’ve been on a team that’s been adding,” Jets defender Brenden Dillon had said of the situation a day earlier, as that arms race had begun to take shape. “You know, you just feel that. Whether that’s getting a depth piece in or a big, important piece in — like we did with [Monahan] — you just feel like you’re going for it. You feel like you’re ready for a stretch run.
“Because we know we’re going to need more than 22, 23 guys to get to where we want to go. Especially when you see your competition around the league adding and making changes. You’re hopeful that your team’s going to give you the best chance to compete for the Stanley Cup.”
Friday morning, Cheveldayoff gave the club his answer, acquiring proven scorer Tyler Toffoli to beef up his top-six even more. The message was clear: the Jets are all-in.
It’s an impressive bit of business from Cheveldayoff. Coming into the deadline, the Jets’ primary need was clear — ranking among the best in the league defensively, with one of the game’s premier netminders holding things down in the cage, the one key question mark was the team’s middle-of-the-pack offence.
The addition of Monahan already helped shift things on that front, the 29-year-old dominating to the tune of eight goals in 13 games since arriving in Winnipeg. But in Toffoli, they get perhaps the best possible option this group could’ve hoped for — a reliable scoring winger, who plays with pace, who throws pucks at the net in bunches and buries a fair amount of them. And, most importantly, a difference-maker who could be added without losing pieces of this Jets roster.
Through 61 games in New Jersey this season, the 31-year-old Toffoli has potted 26 goals in Devils colours — that sum puts him alongside Kyle Connor for the most among Jets forwards right now. He had a career-high 34 last year in Calgary, a total only one Jets scorer topped — Mark Scheifele, with his 42 tallies.
It’s not just that Toffoli seems a sure bet to inject some offence into this promising Jets group, though. It’s his particular fit in this lineup, on this Jets team. With Monahan thriving as the Jets’ 2C, Toffoli figures to line up alongside him as second-line right wing — a spot he’s fairly familiar with.
“Sean and I, we were roommates in junior, so we’ve known each other for a long time,” Toffoli said Friday in his first media availability as a Winnipeg Jet. Toffoli and Monahan spent two seasons as teammates with the OHL’s Ottawa 67s, the pair dominating as linemates during a 2011-12 campaign that saw them combine for 178 points. “I’m excited. It’s an exciting time. The team’s really good, playing really well, and it feels like all the pieces are there. So, it’s just a matter of getting there and trying to fit in as fast as possible, and getting to work.
“Winnipeg, the fans are very passionate — I’m excited to go there and keep pushing for the playoffs, and try and make a run here.”
The eight-time 20-goal-scorer brings something else to this Jets squad, too, as they look to take the next step — Stanley Cup pedigree. Toffoli lifted the hallowed trophy as a Kings rookie back in 2014, and was a key part of the Canadiens’ march to the Cup Final in 2021 as well.
As an added bonus, with the Devils retaining 50 per cent of Toffoli’s $4.25-million salary, the Jets held onto enough cap space to make one final deal before the deadline closed, adding some blue-line depth in right-shot defender Colin Miller — who brings some playoff experience himself, having been part of Vegas’s 2018 run to the Cup Final.
Cheveldayoff and his Jets had a front-row seat to both Toffoli and Miller’s playoff prowess, of course. In 2018, Winnipeg faced Miller and the Golden Knights in the Conference Final during Vegas’s march to the Cup Final. In 2021, as Montreal pieced together their own Cup Final run, it was Toffoli who eliminated the Jets with an overtime goal in Game 4 of the second round.
The pair join Nate Schmidt and Laurent Brossoit as members of this Winnipeg team who’ve endured the grind of a four-round playoff run, the latter having lifted the trophy last year with Vegas, the former having been part of that 2018 run with Miller.
Make no mistake, the decision to add more of that battle-tested playoff experience to the Jets’ room was a conscious one.
“You’re trying to find the right fit,” Cheveldayoff said Friday after the deadline had finally passed. “It was really important we found some players that did have some playoff experience as well. With Toffoli, you’re getting a Stanley Cup champion, that’s going to come into that room and know the grind that it takes to win.
“[Miller’s] got a lot of playoff experience, certainly. … He’s got a big shot, he moves real well, he’s got that experience. He’s got that pedigree.”
In all, with the deadline now passed, Cheveldayoff gave up a 2024 first-round pick, a 2024 third-round pick, a 2025 second-round pick, a 2026 fourth-round pick, and a conditional 2027 third-round pick to bring in Monahan, Toffoli and Miller for the home stretch. Whether it’ll be enough, in the end, to topple the other giants in the West remains to be seen.
But there’s little doubt the GM has made clear his belief in this group.
“We as an organization have been all-in, and we’re going to continue to be all-in,” said Cheveldayoff after reeling in his deadline haul. “It’s all about winning. It has been since the very first day that Mark [Chipman] sat here, when the franchise first relocated. Every decision we make, everything we do, it has a purpose in mind — to ultimately try and win.
“From an organizational perspective, you just want to put them in the best spot that you can to win. And hopefully we’ve done that.”