Making a deal on that day, then adding in the two-week quarantine, would leave the Jets with seven regular season games on their schedule.
"You make a deal to make a deal and you live with the restrictions surrounding it. We're in that type of environment that obviously, we know there are different protocols," said Cheveldayoff. "It would be an easier transition if the rules do change, but I don't know that that's going to affect my decision on making a deal.
"Having said that, if I'm taking a player off of my roster to acquire a player, then I have to take that into consideration as well."
Of course, in the life of a National Hockey League general manager, the trade market is just one thing to keep in mind.
He's kept a close eye on his team, which sits at 17-8-2 and second place in the North Division. In previous seasons, the Jets' size was an asset in the physical Central Division, but when the divisions were realigned for the condensed, 56-game 2020-21 campaign, the Jets were able to adapt to a faster, all-Canadian division as well.
"This division, on a nightly basis, you're facing unbelievable stars on teams that I think make it very, very exciting for the fans to watch and very, very nerve-wracking for management to watch," said Cheveldayoff. "I don't know that there's a team in this division that you're not really focused on a couple of individual players and say: 'We need to make sure we shut these guys down tonight, because they can hurt us.'"
To their credit, the Jets have players that make the opposition's management say the same thing.
Take Nikolaj Ehlers, for instance.
The 25-year-old was just named the NHL's Third Star of the Week after recording six points in three games against the Toronto Maple Leafs.
He leads the Jets in goals with 14, he's second on the team in points with 29, and tops on the team in shots on goal with 84.
In short, he's become exactly the kind of player that Cheveldayoff saw in Halifax tearing up the Quebec Major Junior Hockey League heading into the 2014 NHL Draft.
Which just happens to remind Cheveldayoff of one of his favourite stories.
"We were playing in St. John's in the American (Hockey) League in the playoffs and we had an off day. I had the opportunity to just hop over from St. John's to Halifax and watch a game," said Cheveldayoff. "The attendant upstairs in the press box recognized me and said, 'What are you doing here?' And I was like, 'Well, I'm here scouting. I'm here to watch Ehlers.' He said, 'Well, where are you guys drafting?' And I said, 'Well, ninth.' 'Well, you're not going to get him at ninth', he says. 'He's going to be long gone before then.' 'Well, I'm just here to enjoy the game,' I said. And enjoy the game I did, because he was spectacular in that game."
He had similar praise for other homegrown organizational talent like Mason Appleton, the team's sixth round pick in the 2015 NHL Draft who is enjoying a career year offensively.
He's liked what he's seen from Neal Pionk, now in his second year in a Jets jersey, and he's also been happy with what Pierre-Luc Dubois has brought since being acquired in January.
"I think we're really just scratching the surface with Pierre-Luc, and I think the three-week timeframe was difficult for him to deal with," said Cheveldayoff. "Like, right now watching Pierre-Luc with Nikolaj and Kyle, it's exciting to think just the chemistry that's being built there and how they're going to continue to grow. Anyone in our top-six I think you can probably mix and match now, and like a lot about those lines."
Pionk and Dubois came to the Jets via trade, which only underscores the importance of the next month or so leading up to the trade deadline. To make things more complicated, there is also an expansion draft looming - with the Seattle Kraken set to play their first season in 2021-22 - and a list of eight unrestricted free agents he'll have to work to chip away at.
"Certainly it might determine how much of an asset you want to give to acquire a player if it puts you in those situations," said Cheveldayoff of the expansion draft. "But as far as the UFAs, we're hopeful that we can continue to do business as usual, whether it's in a pandemic or not. I think the hard part is the flat cap moving forward. That makes it very uncertain how to allocate the different resources. So as far as that goes, we'll try to make it as "business as usual" as possible."
While it can be difficult to see past the growing list of decisions Cheveldayoff and his team have in front of them, the Jets GM also has his eye on the future.
Yes, there is the NHL Draft to consider - it's a big part of how Cheveldayoff likes to build the organization - but he's also looking forward to seeing a number of his colleagues in person again.
He's grateful the NHL is able to continue, but like many, Cheveldayoff has gained a new perspective on how lucky he is to work in the game he loves.
"You miss the interactions, even though you're here with the players and here with the coaches, you miss those kind of real close interactions and you're always still trying to do things at a distance. You miss the interactions with the other general managers and scouting opportunities that you do have to go watch players live," he said.
"It's been an opportunity to really reflect on how much I just really, really love the game, and really love the opportunity that I have here right now to be part of this organization and to be part of the National Hockey League."
