The off-season is about a month old, which means general manager Brad Treliving is just getting started. Calgary has lots to figure out coming off a disappointing five game playoff exit and Treliving has never been one to be passive. From potential trades to free agency, the Flames are staring at one of the most important summers in quite some time. Nothing looms larger, though, than Matthew Tkachuk’s pending contract negotiation.

Matthew Tkachuk’s contract

There is so much to consider when trying to determine what Tkachuk’s new deal is going to look like, and when he’s going to sign it. The fact Tkachuk is part of a massive class of high-end restricted free agents makes projecting very difficult. It also doesn’t leave me overly optimistic this is going to get done anytime soon.

This RFA crop includes Mikko Rantanen, Mitch Marner, Patrik Laine, Brayden Point, and Sebastian Aho, to name only a few. For virtually every player in the conversation, there isn’t much benefit to signing early. Specifically for players in the middle of this pack like Tkachuk, the incentive to get out in front isn’t really there. As such, it wouldn’t surprise me to see this drag into August.

Then there’s the matter of what the deal actually looks like, whenever it gets signed. Are the Flames willing to sign Tkachuk to the biggest contract in team history? If they’re keen on locking Tkachuk up for seven or eight years, they won’t have much of a choice.

The biggest deal in team history is currently owned by Sean Monahan; he signed for seven years and $44.625 million three years ago. With the NHL’s current economics, I can’t see the Flames getting Tkachuk for a similar term at less than Monahan’s $6.375 million average annual value.

Calgary’s highest AAVs are owned by Mark Giordano and Johnny Gaudreau; both count $6.75 million against the cap. To keep Tkachuk under any rumoured “internal cap”, the only option would be a bridge deal, likely for three years. Two years is too short, four years gets Tkachuk to free agency, and anything longer starts to buy UFA years, which come at a premium.

Bridging Tkachuk is helpful in the short term; the Flames would get him at a lower cap hit for three years as they try to maximize their competitive window. The downside, of course, is what happens after those three years. If Tkachuk continues to produce at point-per-game rates, what could be a $7.5 million AAV today is going to be a whole lot higher come 2022.

Draft weekend

Treliving gets his work done at the NHL Draft. He’s worked five drafts as GM and has made a trade every single time, and usually not of the small variety. I don’t expect that trend to change next month in Vancouver, and I’m led to believe Treliving is ready to execute another significant move.

Aside from 2014, all of Treliving’s draft weekend acquisitions have been big ones, which makes it four straight years. Furthermore, Treliving was only on the job for about six weeks prior to his first draft, which leads many to suggest the Bollig acquisition was more of a Brian Burke decision.

With names like TJ Brodie and Michael Frolik connected to plenty of trade innuendo, it shouldn’t be a surprise if the Flames leave Vancouver as one of the biggest newsmakers for a fifth straight year. While Calgary would be fine using their first round pick (26th overall), we’re talking about a team knocking on the door. Don’t be stunned if Calgary doesn’t pick in the first round for the third time in five years.

Other contract negotiations

While Tkachuk’s deal will garner the most attention this summer, the Flames have a few other interesting contracts to figure out, too. In the immediacy, David Rittich’s new contract poses an interesting dilemma. Is Calgary ready to go multiple years with Rittich for a long-term payoff? Or is the more risk-averse one-year deal the approach?

The Flames also have interesting negotiations ahead with a trio of forwards: Sam Bennett (RFA), Andrew Mangiapane (RFA), and Garnet Hathaway (UFA). All three showed growth in 2018-19, while the latter two took significant steps forward.

Finally, Rasmus Andersson becomes eligible for a contract extension July 1st, which presents an opportunity for Calgary. With one year remaining on his deal, the Flames have a chance to pounce and lock up an extremely promising defenceman long-term, even if it means absorbing a little risk. If his camp is into it, I see very little downside going five or six years with Andersson as soon as he becomes eligible.

Figure out the goaltending situation

Tackling the above task has a number of layers. It starts with getting Rittich signed as discussed above, but goes beyond that. Calgary needs to decide, if they haven’t already, if they see Rittich as a number one. If the answer is yes, he needs to be given the opportunity, and playing time, to reflect that starting in October.

The Flames also have to decide if Mike Smith is back next season. The pending UFA started all five of the team’s playoff games, but also turned 36 in March and struggled for much of the regular season. If Smith is open to returning as part of a tandem, the conversation about re-signing him has merit. If he’s focused on remaining a clear cut number one, it doesn’t make any sense.

I’m not anticipating a Smith return, which would force Calgary to find a solid partner for Rittich. I don’t believe the Flames are confident Jon Gillies is that guy, so a trade or free agency would be the next step. Cam Talbot, Curtis McElhinney, and Thomas Greiss (trade) are all very interesting options Calgary could explore.