We still don’t know exactly when next season is going to start, but assuming we’re in and around two months away, the Flames still have a lot to get done. A pair of contracts with somewhat firm deadlines lead the pack, but that’s not the only decision general manager Brad Treliving has to make in the next couple months.

Oliver Kylington’s contract

Kylington is Calgary’s lone restricted free agent contract still on the board, which is why this feels like the most pressing matter. The fact this deal isn’t done yet is interesting, mainly because it seems rather straightforward from the outside. Kylington has 87 NHL games to his name, so doesn’t have a ton of leverage to push for anything more than an affordable, short-term deal.

So what’s holding this up? Are we talking about a standoff on a one-way or two-way contract? Is the Kylington camp looking for assurances he won’t be pushed out of the lineup or to the American League if the team is looking for roster and/or cap flexibility? When I spoke to Treliving last month, he gave the impression Kylington was still someone the team had factored into their plans.

“Oliver sometimes is the forgotten guy,” the general manager told me. “I don’t mean that in any disrespect, but sometimes that’s on us more than anything else. We’ve gone through two trade deadlines where we’ve added some depth on the blueline, in some cases because we were banged up and injured and needed some more bodies, as was the case this past year. Sometimes that squeezed Oliver.

“He’s improved dramatically, not only from when he first entered the organization as a young guy, but when he first entered the NHL. He’s able to defend much better, his decisions with the puck are much better. There’s a lot of guys who as they grow, as they mature, as they get more games under their belt, they’re that much more comfortable and confident. I think we’ve seen that in Oliver. He’s still very much part of the plans here.”

I still think Kylington is a nice option to have next season and beyond. Both Juuso Valimaki and Chris Tanev have had trouble staying healthy. Newly signed Nikita Nesterov hasn’t played in the NHL since 2017. Kylington may have his limitations, but having him in the fold is still prudent for the Flames. And, as a 23-year-old defenceman, it’s not like he’s done developing.

Connor Zary’s entry level deal

Calgary’s latest first round pick likely isn’t a factor to play NHL games this season. But the Flames do have an interesting Dec. 31 deadline to sign Zary to his first contract and also benefit from an entry level slide. Ryan Pike laid it out really well last month, and I’ll give you a quick refresher.

Because his birthday is after Sept. 15, Zary becomes eligible for a sliding contract if two conditions are met: he signs his ELC before Dec. 31, 2020 and doesn’t play more than nine NHL games in each of the next two seasons. Assuming he’ll spend the coming season in the Western Hockey League, scheduled to start on Jan. 8, his entry level deal will slide (not have a year burnt). That puts the spotlight on 2021-22.

That’ll be Zary’s 20-year-old season in junior, which means he’ll also be American League eligible for the first time. Depending on his development, Zary might not be ready for full-time NHL hockey by then. In that case, Calgary would likely still prefer for him play in the AHL. In that circumstance, as long as Zary doesn’t play ten or more NHL games, his contract would slide again.

In this circumstance, Zary could play an entire year of pro hockey without burning a year of his entry level deal. It’s a nice option to have if things play out in that manner and it all hinges on whether the Flames sign Zary prior to Dec. 31. The team knows this as well as we do, so you can pretty much guarantee they’ll do just that.

The World Juniors

Speaking of Zary, he’s among numerous Calgary prospects eligible to play at the 2021 World Juniors in Edmonton. Zary is one of two Flames draft picks vying for a spot on Team Canada, although as an 18-year-old, he enters selection camp later this month as more of a long shot. Many experts believe the first round pick preceding him has a better chance of suiting up for his country.

Calgary’s first pick in 2019 was Jakob Pelletier and he enters selection camp extremely motivated. An injury derailed Pelletier’s chance to play for Canada in last year’s tournament, but he’ll have a good chance this time around. Pelletier is QMJHL Val-d’Or’s captain and is able to fill multiple roles, which is something Hockey Canada covets when selecting their squads.

Team USA will almost certainly be backstopped by 2019 seventh round pick Dustin Wolf after appearing in one game last year. Wolf was last season’s CHL and WHL goaltender of the year and it would be a shock if he doesn’t get the bulk of the starts for the Americans. Centre Josh Nodler, a 2019 fifth round pick, is also eligible after completing his first year with Michigan State last season.

The heaviest Flames content might be on the Russian team. Defenceman Yan Kuznetsov (second round, 2020), forward Ilya Nikolaev (third round, 2019), and goaltender Daniil Chechelev (fourth round, 2020) are all eligible for Russia. Winger Lucas Feuk, a 2019 fourth round pick, has a chance to make Sweden’s team, although it sounds like that’s an outside shot.

Dillon Dube and Juuso Valimaki extensions

While not of the urgent variety prior to next season, there are a pair of potential core players entering the final years of entry level contracts. After a strong playoffs, forward Dube will enter next season with high expectations. If Dube meets them, knowing his offensive upside, that contract negotiation could end up being very interesting.

Currently tearing it up in Finland, the big thing for Valimaki is staying healthy and spending the entire year in the NHL. We know how highly Calgary thinks of Valimaki, though, which also makes this negotiation fascinating. Because injuries have limited Valimaki’s professional resume, I’m curious if that might give the Flames more leverage to sign him long-term on a team-friendly number.

Finally, Sam Bennett is eligible for a contract extension, too. As of now, Bennett would likely find himself number eight on the list of seven forwards on Calgary’s protection list for the Seattle expansion draft. Additionally, Bennett will have a high qualifying number and arbitration rights next summer, which makes this coming season one to watch.