WINNIPEG - At the best of times, Kevin Cheveldayoff's to-do list is lengthy, and this off-season will be no different for the Winnipeg Jets general manager.
Now that exit meetings with the players and coaching staff are complete, Cheveldayoff knows he needs to move his chess pieces strategically amidst all the question marks the next few months will bring.
"Obviously you take some time to de-compress and to evaluate and re-evaluate, go over just the past season, dissect it a little bit," Cheveldayoff said of the 2020-21 campaign. "We're getting ready for the draft, we're getting ready for the expansion draft. And then obviously getting ready for free agency. So there's lots of work behind the scenes in those regards."
Good thing he knows where to start.
When he goes over the season that just ended, he knows there will be some highs - including the first round sweep of the Edmonton Oilers - and some lows, no doubt including the series loss to the Montreal Canadiens in the second round of the Stanley Cup Playoffs.
He described the work of Paul Maurice and his coaching staff as "exemplary" as they navigated a season with additional protocols, daily testing, and a condensed schedule.
He credits the players for buying into the style of game that needed to be played against the Oilers in the postseason, and for doing everything they could to stay healthy during a difficult season.
"We went through a very long period of time this year where we didn't lose back-to-back games and it was because of these players putting it out there," Cheveldayoff said. "In order to make the playoffs in a shortened season like this, you couldn't afford to have too many bad stretches."
Video: YEAR END | Kevin Cheveldayoff
Due to the team staying extraordinarily healthy throughout much of the season, players on the required taxi squad didn't see as much game action as the organization would've liked.
With no road games in the Central time zone, the Jets needed to keep certain players with them on road trips so they could adhere to protocols. That meant that those not in the line-up - like Jansen Harkins, Kristian Vesalainen, and Ville Heinola for example - went long stretches without seeing game action.
Luckily for Heinola, he was still able to play 50 total games this season (split between Liiga, the American Hockey League, the World Juniors, and the NHL).
"This was a challenging year not just for Ville Heinola, but for everybody from a development standpoint," said Cheveldayoff. "You look at the OHL this year and all those players never got a chance to play. I think you do what you can, we put everyone in the best opportunity to have an opportunity to play for the Jets if that was going to be what was in the cards for them."
Heinola was selected 20th overall in the 2019 NHL Draft, one year before Cole Perfetti was taken 10th overall in 2020 - a draft that was held virtually on July 23 and 24.
The 2021 version of the NHL Draft will also be virtual. The challenge ahead of the amateur scouting staffs around the National Hockey League is immense - rank draft-eligible players, based on limited viewing due to the global pandemic, so decisions that have an incredible impact on an organization's future can be made with as much confidence as possible.
As it stands, the Jets will select 17th overall. It will be their first of four picks, with the other three coming in the second, third, and fifth rounds.
"We feel we have one of the best amateur (scouting) staffs in the game," said Cheveldayoff. "We have a real strong, I guess, sense of what we want in players and how we evaluate them and how we rank them. So we're going to obviously rely on that strength."
Speaking of drafts, another item on Cheveldayoff's list is the expansion draft, which comes on July 21. It will have the same rules as in 2017 when the Vegas Golden Knights came into the league.
That summer, Chris Thorburn was selected off the Jets roster by Vegas.
"Every situation is going to be different," said Cheveldayoff. "Every organization is going to approach things differently, depending on their cycle and what they have coming from within their system to augment or develop a player to fill that hole. It will be an interesting time."
Up next, free agency, which gets underway on July 28.
The Jets have nine unrestricted free agents - Paul Stastny, Mathieu Perreault, and Laurent Brossoit among them - and five restricted free agents, including Andrew Copp and Neal Pionk.
Along with trades and the NHL Draft, free agency is another key part of roster composition.
It's also where Cheveldayoff's game of chess gets incredibly complicated.
Adding to the roster via free agency can be tricky.
"We've got some contracts we do need to take care of ourselves, obviously on the RFA side," said Cheveldayoff. "So there's lots of work on that regard that will dictate what we have available to be aggressive or not, if there's players that fit that mould."
Sometimes, to make moves to make the team better, teams have to part with draft picks.
"At the trade deadline, you can throw a first-round pick like it's nothing and come the night before the draft, the first-round picks are like gold," said Cheveldayoff. "We had success, obviously, trading for Stas that first time, so you keep on doing it. But then when you're sitting at the table on draft day and your scouts are looking at you and going, 'Ah, we love that guy and we love this guy and we love that guy,' then you get the angst from a management standpoint that you've got to try to go and get some picks."
Players like Mark Scheifele, Kyle Connor, Nikolaj Ehlers, Josh Morrissey, and Connor Hellebuyck are just five of the 13 drafted Jets that played for the team in the postseason.
Those players are also a key part of the core identity of the Jets.
An identity Cheveldayoff wants to keep building.
"You take pride in all of those kind of things because development of a player, development of an organization doesn't happen overnight," he said. "You can't just rely on throwing money against the wall on free agency to think you're going to develop an organization that can try to win on a regular basis.
"We've been fortunate to make the playoffs over the last couple of years and that's because I think we're all pulling in that same direction, coaches, management, ownership, scouting, player development, players. That's something I'm proud of."