Over the weekend, the Montreal Canadiens sent a fifth-round pick to the Carolina Hurricanes in exchange for the negotiating rights to defenceman Joel Edmundson.

Their gamble worked — the club signed Edmundson, who was scheduled to hit unrestricted free agency, to a four-year pact worth $14-million earlier this week – and it’s worth wondering if we’ll see more of these kinds of deals between now and the beginning of October as free agency officially heats up and more teams map out what will surely be one of the strangest off-seasons on record.

Normally, there’s a crucial period right before free agency officially opens that allows teams to talk to pending UFAs. This courting period has been nixed this year to accommodate a shortened off-season, which means teams may need to be extra strategic about how they’re pursuing players, including tossing a draft pick in the ring like Montreal did for a possible payoff in the form of a free agent signing.

As we near the Oct. 9 opening of free agency, here’s an updated look at the biggest names looking to sign on the dotted line this fall…

1. Alex Pietrangelo, D, St. Louis Blues

Age: 30

2019-20 cap hit: $6.5 million

Both Pietrangelo and general manager Doug Armstrong have made it clear they’d like to get a deal done, and time is on their side – but the math complicates it.

Armstrong cleared up $4.35 million earlier this month when he dealt goaltender Jake Allen to the Montreal Canadiens, paving the way for Ville Husso (and his affordable $750,000 cap hit) to step into the backup role behind Jordan Binnington.

“At the end of the day, it’s a math equation,” Armstrong told reporters upon moving Allen, when asked about what this means for being able to lock up his captain.

So, math-wise, where does that leave the Blues in a flat-cap landscape? Looking ahead to next season, CapFriendly shows St. Louis with about $69.8 million invested in 14 forwards, five defencemen and one goaltender.

Armstrong will also need to address pending RFA defenceman Vince Dunn, after looking after his other would-be RFAs like Sammy Blais and Marco Scandella this past spring.

That leaves the captain, who’s expected to garner between $8 million and $9 million per year on a long-term deal – a fair price when you look at his performance over the course of this season and his importance to the Blues franchise as a whole.

“Obviously, I want to stay a Blue. Of course I do,” Pietrangelo told reporters last month, during his end-of-season availability via Zoom following the Blues’ first-round loss to the Vancouver Canucks. “It’s the only place I’ve known professional hockey.”

2. Taylor Hall, LW, Arizona Coyotes

Age: 28

2019-20 cap hit: $6 million

Ten seasons into his NHL career with just two short playoff stints to show for it, Hall’s priority heading into the biggest decision of his career is no surprise.

“I think honestly it’s probably all winning,” Hall told reporters in August, following his Arizona Coyotes’ Round 1 loss to the Colorado Avalanche. “Any player at this stage in their career who’s had the career I’ve had, 10 seasons only making the playoffs twice, that’s really what I’m after. We’ll see what happens there.”

So, can the Coyotes win? That will be just one of the many questions hovering of the franchise this off-season, along with who will be their general manager, how they’ll recover from the harsh punishment handed down for violating the league’s combine testing policy and whether captain and top defenceman Oliver Ekman-Larsson is in fact on the trade block. That’s a lot of major questions for one team to handle, and that’s in addition to navigating the salary cap.

Sportsnet’s Rory Boylen looked at a handful of teams that could potentially land the top forward of the 2020 class, with the on-the-rise Montreal Canadiens ($18.5 million in projected cap space) and Colorado Avalanche (about $22.3 million) particularly intriguing.

In 30 games with the Devils plus 35 with the Coyotes upon being dealt to the desert, Hall tallied a combined 16 goals and 36 assists for 52 points through 65 regular season games in 2019-20 – a far cry from his 39-goal, 93-point Hart-winning campaign with New Jersey in 2017-18, but a good sign that he’s getting back on track after two years of injuries and trade rumours.

Through nine post-season games with Arizona, the Calgary native had a pair of goals and six points, matching his previous playoff totals from 2017-18 in a five-game run with New Jersey.

Hall acknowledged the current financial landscape of the league due to COVID-19.

“I don’t think the money is going to be what it was before COVID or before this season, but that’s fine,” he said. “I think we get paid a lot of money to play a game and we’ll see what happens.”

3. Torey Krug, D, Boston Bruins

Age: 28

2019-20 cap hit: $5.25 million

Both Krug and Bruins general manager Don Sweeney have expressed a desire to extend this relationship, and while Sweeney told reporters earlier this month he plans to begin those talks now that Boston’s season is over, there’s plenty of uncertainty about whether the two sides will be able to work something out while also keeping room for pending RFAs Matt Grzelcyk and Jake DeBrusk.

Krug has spent his entire NHL career to date with the Bruins – first on back-to-back one-year bridge deals, followed by the four-year pact that’s expiring now – and is looking for a long-term commitment. He’d like that to be with Boston, but made it clear he won’t be signing another short-term deal to stay.

“I’m very opposed to that,” he told reporters earlier in September. “I’ve bet on myself. I’ve taken shorter-term deals, less amount of money my whole career now. This is my time in terms of my value at its peak. I have the ability, I’m in a position now where I need to make the most of it.”

4. Robin Lehner, G, Vegas Golden Knights

Age: 29

2019-20 cap hit: $5 million

Goaltending was the biggest storyline for the Golden Knights this post-season – having two starting netminders will do that — so it’s no surprise that the club’s crease remains in the spotlight as they stare down the off-season after being ousted from contention by the Dallas Stars in the Western Conference Final.

“We don’t have those answers for you right now,” general manager Kelly McCrimmon told reporters on Wednesday, addressing goaltending. “But [the] first order of business, I think, in many respects, is to sort that out.”

Two one-year deals and a deadline trade have seen Lehner suit up for three different teams in the past two seasons, and he’s thrived with all of them. His dominance this post-season (9-4 record, 1.84 goals-against average, .924 save percentage and four shutouts) has ultimately hoisted him from popular UFA-to-be to the hottest goaltender on the market.

That is, if he even makes it to free agency. As his incredible playoff numbers indicate, Lehner looks right at home in the Golden Knights crease and after all signs initially pointed to the 29-year-old being a short-term rental for a long post-season run, it sounds like both team and player are looking to keep this relationship going.

Golden Knights reporter Jesse Granger of The Athletic wrote last week he believes the team is planning to lock up Lehner with a long-term contract extension, and wrote that those talks may already be underway.

This could get complicated, though, as starter-turned-backup (and fan favourite) Marc-Andre Fleury still has two more seasons remaining on the three-year extension he signed with the club back in 2018, coming in at $7 million per season.

5. Tyson Barrie, D, Toronto Maple Leafs

Age: 29

2019-20 cap hit: $5.5 million (this AAV is split between Colorado and Toronto)

Barrie’s time in Toronto didn’t go how he or the Maple Leafs expected, making a clean split in free agency a certainty for the two sides.

“I wish I would’ve left a little more of a stamp on the series,” Barrie, who didn’t register on the scoresheet through all five games of the qualifying round against the Columbus Blue Jackets, said in August following the conclusion of Toronto’s season.

Asked about where he might land and what kind of contract he’s looking for going forward, Barrie said, “at this point I have no idea what the future holds.”

It’s safe to say he will be prioritizing chemistry and opportunity in an effort to regain his game with another squad.

The Maple Leafs have already made a few moves this off-season, sending Kasperi Kapanen to the Penguins, and will reportedly let forward Kyle Clifford walk in free agency.

6. Jacob Markstrom, G, Vancouver Canucks

Age: 30

2019-20 cap hit: $3.67 million

In less than a week, the Hockey Twitter tide shifted from an urgent call to re-sign Markstrom to a sudden consensus that Thatcher Demko’s the guy after the rookie broke out in the playoffs and nearly broke the Golden Knights in the process. But for general manager Jim Benning, this isn’t a one-or-the-other decision.

“[Coach Travis Green] is a big believer in having two good goalies,” Benning told reporters during his end-of-season availability earlier this month. “With the travel schedule we have during the regular season, I believe we need to have two good goalies.”

Benning told reporters that Demko’s emergence doesn’t change the team’s motivation to sign Markstrom, who is expected to earn a nice raise to the tune of around $6 million per year, and indicated that those negotiations to bring back the veteran will start this week.

“Jacob is an important guy in our group,” Benning explained. “He’s a leader and he was our MVP over the regular season, so we’re going to try to figure out a way that makes sense for us and that makes Jacob and his agent happy, to try to figure out a deal to get him signed.”

Staying the course and re-signing the veteran goalie, who is without a doubt the Canucks’ MVP of 2019-20, would pave the way for one heck of a fine goalie tandem in Vancouver with starts split down the middle, but it could also set the team up for trouble when it’s time to start handing out protected roster spots ahead of the Seattle expansion draft as every team is only able to protect one netminder.

Sportsnet’s Elliotte Friedman touched on the topic in his latest edition of 31 Thoughts:

Once eliminated, Canucks GM Jim Benning began making his due-diligence calls around the NHL. My sense is he’s trying to see if he can sign his UFAs and work backwards from there. There’s a desire for all of Jacob Markstrom, Christopher Tanev and Tyler Toffoli to return, but there are challenges (although there’s some positivity this week with Toffoli). The Canucks will want flexibility into the expansion draft with Markstrom and Thatcher Demko. My sense is Markstrom would consider movement protection after Seattle makes its picks, but could want contract concessions in return. Vancouver has a number it won’t go past. The challenging thing for everyone involved is that I’m hearing the market for Markstrom is strong. – Elliotte Friedman, 31 Thoughts

7. Mike Hoffman, RW/LW, Florida Panthers

Age: 30

2019-20 cap hit: $5.1875 million

Florida’s got a lot of question marks right now. The team parted ways with general manager Dale Tallon following its qualifying-round loss to the Islanders last month, and it’s safe to say plenty more changes will be on the way now that new GM Bill Zito takes over and puts his own stamp on the club.

Hoffman looked like a sure rental candidate at the deadline but ultimately wasn’t moved. His strong performance through four games against the Islanders – three goals and five points – should make him a popular player among teams looking for another scorer to contend.

8. Braden Holtby, G, Washington Capitals

Age: 30

2019-20 cap hit: $6.1 million

At the beginning of the season, Holtby was a no-brainer as the top goaltender on the list of pending UFAs at his position, but the standout play of peers Lehner and Markstrom have seen the spotlight shift. Holtby’s own struggles this year have complicated his future outlook, and back-to-back early playoff exits for the 2018 Cup champs have made the Capitals’ next moves tough to predict.

It’s now looking more and more likely that we’ve seen the last of Holtby in All Caps, as Washington general manager Brian MacLellan told reporters on Tuesday that he expects Holtby to reach free agency.

“I’d expect him to go to free agency. The goalie market is unusually deep this year,” MacLellan said during a Zoom call, after the team announced the hiring of Peter Laviolette as head coach. “I talked to his agent last week briefly about where he’s at and the kind of opportunities he’s looking for.

“I would assume he goes to free agency and we’ll keep in contact with him throughout the free agency period and see if he’s getting what he wants.”

Holtby struggled to find consistency this past season, and the emergence of rookie netminder Ilya Samsonov brought added urgency to Washington’s decision, especially when you consider the upcoming expansion draft next year. That Stanley Cup on his resume, however, should see him land a decent deal — wherever that may be.

9. Evgenii Dadonov, RW, Florida Panthers

Age: 30

2019-20 cap hit: $4 million

Another question mark for Florida.

Dadonov quietly put up back-to-back 28-goal campaigns down in Florida, tallying 65 and 70 points in his past two seasons, and a scoring spree in January had him just three goals shy of that total through 69 games this season. A quiet post-season didn’t do his stock any favours, but he’s one of the more low-key intriguing names to watch as one of the league’s most underrated sharpshooters.

10. Tyler Toffoli, RW/LW, Vancouver Canucks

Age: 27

2019-20 cap hit: $4.6 million

After a down year in 2018-19 with 13 goals and 34 points on a floundering Kings squad, Toffoli got off to a strong start in Vancouver upon being traded in February.

An injury early in the playoffs had us wondering if we’d seen the last of him this year, but the 28-year-old came out flying upon his return in Game 2 of the second round against Vegas. His seamless fit with the Canucks makes him a priority for Benning in what’s shaping up to be a busy off-season in Vancouver with defenceman Chris Tanev also seeking a new deal.

11. Mikael Granlund, C/RW, Nashville Predators

Age: 27

2019-20 cap hit: $5.75 million

With GM David Poile promising changes ahead, there’s really no question that Granlund will be wearing a different sweater come 2020-21. With a flat cap and a down year on the stat sheet, Granlund could be a strong candidate for a short-term deal somewhere to get him back to his playmaking ways.

12. T.J. Brodie, D, Calgary Flames

Age: 29

2019-20 cap hit: $4.65 million

Flames GM Brad Treliving said in the spring he wanted to bring both Brodie and fellow rearguard Travis Hamonic back into the fold. But with the flat cap, will he be able to?

As the more offensively gifted of the Flames’ two pending UFA d-men, Brodie could be the more likely — but less affordable — signee in Calgary.

Brodie’s name has been in trade rumours before. Now, with another disappointing post-season in the books, the question in Calgary is whether (or maybe how much) Treliving will opt to split up his core and revamp his roster.

13. Travis Hamonic, D, Calgary Flames

Age: 29

2019-20 cap hit: $3.857 million

Hamonic, who made the decision to opt out of the NHL’s restart this summer to be with his family, has been a steady presence in Calgary and would no doubt be a smart signing for Treliving to make. The GM has a little more cap flexibility than some of his NHL peers, but how much will he devote to his blue line?

14. Sami Vatanen, D, Carolina Hurricanes

Age: 28

2019-20 cap hit: $4.875 million

Vatanen had to wait a while to suit up for a game with the Hurricanes, the team that acquired him from the Devils at the deadline, due to the lower-body injury that had him sidelined at the time of the league hiatus. Considering how little he played with his new teammates, Vatanen fit in well with the Hurricanes. The club’s depth at the position makes them unlikely to bring him back, however.

Injuries have prevented the rearguard from ever being able to play a full season, which will factor into his next deal.

15. Anton Khudobin, G, Dallas Stars

Age: 34

2019-20 cap hit: $2.5 million

Every post-season, we re-learn the importance of having not just one solid goaltender but two. This year’s lesson comes from Khudobin. The veteran netminder has started almost every single one of the Stars’ 21 games this summer as No. 1 netminder Ben Bishop has been sidelined as “unfit to play.”

Lehner, Markstrom and Holtby are the biggest names on the goalie market, but Khudobin will be a popular name, too, for contenders looking for an insurance policy – that is, if the Stanley Cup Final-bound Stars dare let him go.

16. Corey Crawford, G, Chicago Blackhawks

Age: 35

2019-20 cap hit: $6 million

Like Khudobin, Crawford could be a solid backup/1B option on a short-term deal for a contender going forward should he part ways with the Blackhawks.

While his $6-million seasons are over, his career isn’t. We haven’t had many opportunities to see Playoff Crawford of late, but we got a pretty decent show this summer when the veteran netminder backstopped Chicago to an upset victory over the Edmonton Oilers in the qualifiers and kept the club alive in Game 4 of Round 1 against the Vegas Golden Knights.

17. Ilya Kovalchuk, LW, Washington Capitals

Age: 36

2019-20 cap hit: $700,000

Montreal’s Kovalchuk experiment got off to a great start — the veteran proved he’s still got a little magic left in him, and his success looked even better with a $700,000 price tag attached — and saw the club flip him to the contending Capitals for a profit at the deadline. He fell flat in the playoffs with Washington, but it feels likely this wasn’t the last we’ve seen of Kovalchuk in le bleu, blanc et rouge. He’s a strong candidate to return to Montreal as a free agent on another low-cost contract.

18. Erik Haula, LW, Florida Panthers

Age: 28

2019-20 cap hit: $2.75 million

A string of injuries has hindered Haula’s ability to match the success he had with the Golden Knights in 2017-18, and he wasn’t able to strike up any chemistry with the Panthers upon being traded to Florida at the deadline. There’s no doubt he’s been a much-loved and valuable member of each team he’s played on, but durability will factor into his next deal.

19. Wayne Simmonds, RW, Buffalo Sabres

Age: 31

2019-20 cap hit: $5 million

Simmonds has struggled to find his stride since landing in Nashville at the 2018-19 deadline. Since then, he’s scored just nine goals and 28 points in 85 games split between the Predators, Devils and Sabres. He’s just three seasons removed from back-to-back 30-plus-goal campaigns and should be a top candidate for a short-term deal on a team that can help revive his career.

20. Kevin Shattenkirk, D, Tampa Bay Lightning

Age: 31

2019-20 cap hit: $1.75 million

He’s not the top UFA candidate he was just a few years ago, but Shattenkirk’s impact on Tampa Bay’s blue line – both in leadership and playmaking — should put him among a number of strong blue-liners ready to sign quickly if he hits the open market.

Other notable pending UFAs to keep an eye on: Joe Thornton (SJ), Zdeno Chara (BOS), Chris Tanev (VAN), Alex Galchenyuk (MIN), Thomas Greiss (NYI), Cody Eakin (VGK), Cody Ceci (TOR), Justin Schultz (PIT), Michael Frolik (CGY), Vladislav Namestnikov (OTT), Erik Gustafsson (CHI), Pat Maroon (TB), Zach Bogosian (TB), Kyle Clifford (TOR), Radko Gudas (WSH), Justin Williams (CAR), Dustin Byfuglien