Handling free agents of all varieties might be the most important aspect of an NHL general manager’s job.

Whether we’re talking about re-signing a veteran unrestricted free agent to projecting how a younger restricted free agent skater will evolve and grow into a deal, this is the heartbeat of an organization’s ability to properly evaluate and then value talent.

It’s an inexact science, and if it was easy, we wouldn’t have had such a clear playoff picture two months out from the end of the regular season.

Organizations also have to find ways to balance the human element against shrewd asset management. For instance, Kris Letang has meant a lot to the Pittsburgh Penguins over the years, but what would the team do if he asked for a contract worth $9 million or more a season?

They would probably have to make the tough choice to let him walk as a free agent. That’s just one example of the kinds of difficult choices GMs around the NHL will be facing in the comings months as they try to lock in their better players at fair value.

Let us know how you would handle your favorite team’s most difficult offseason free-agent choice down in the comments below.’

Anaheim Ducks: Sonny Milano (RFA)

The future of the Anaheim Ducks belongs to Trevor Zegras and Troy Terry. That was made clear at the trade deadline when fresh general manager Pat Verbeek traded away veterans like Hampus Lindholm and Josh Manson instead of signing them to long-term extensions.

Don’t overlook how important Sonny Milano has been as a plug-and-play option for head coach Dallas Eakins all season long, though. Zegras drives the bus when the two line up together, there is no questioning that. But Milano isn’t just a lucky passenger, riding on the coattails of one of the NHL’s blossoming superstars.

That’ll make figuring out just how much to pay him as an RFA this summer interesting. Verbeek has made it clear that he doesn’t want to hand out long-term contracts to his pending free agents. At least that was the case with Lindholm, who was slated to become a UFA this summer.

Milano is 25, so he’s not in decline yet, but he’s no spring chicken either. There’s also the fact that, until this year, the forward had failed to make an impact through half a decade with the Columbus Blue Jackets and two campaigns in Anaheim.

The wing would be wise to walk the tightrope between those two realities, as Verbeek doesn’t seem the type of GM you’d want to play hardball with.

Arizona Coyotes: Lawson Crouse (RFA)

Everything the Arizona Coyotes are doing right now is in the name of avoiding tough free-agent choices for the time being. They are trading away just about any player who has value, and odds seem good that they’ll move Jakob Chychrun over the summer when it’s easier to swing a deal like that.

It seems highly unlikely that aging veteran free agents like Phil Kessel, Loui Eriksson, Jay Beagle or Anton Stralman will be brought back unless it’s on minimum deals following a lack of interest from other NHL clubs. Those choices aren’t particularly tough ones for general manager Bill Armstrong.

Lawson Crouse is conceivably the toughest player coming up on the docket. He’s firmly in the team’s second tier of producers, but even teams that are taking the barebones approach need talent. Crouse is 24 and could be a more long-term part of the rebuild, like Clayton Keller.

With Armstrong looking to shed monetary commitment to Chychrun, however, it remains to be seen whether or not the Coyotes are interested in giving anyone term for now. How they approach Crouse will be telling.

Boston Bruins: Patrice Bergeron (UFA)

We arrive at the first big name on our list, and it’s a doozy. Patrice Bergeron is synonymous with the Boston Bruins and is a core piece of their identity both on and off the ice. The same could have been said for Zdeno Chara when he was allowed to leave as a free agent in 2020.

The towering blueliner was 43 at that juncture, however, and it was time to turn the top spot over to Charlie McAvoy—a choice that has turned out swimmingly for the B’s.

Bergeron is 36, but he’s still at the peak of his powers. He’s the favorite to win the Selke Trophy as the best two-way forward in the game and could even receive some votes for the Hart Trophy. Time comes for us all, though, and Boston will have to weigh what the captain has done against what he can realistically do in the coming years.

His current cap hit is $6.875 million, which means he’s due for a pretty significant raise. At Bergeron’s age, this will also likely be his last chance to cash in on a big-money deal. Boston is projected to have around $4.5 million in space to work with and will also need to ink David Pastrnak to a new deal before the 2023-24 offseason when he’s slated to hit free agency.

It will be fascinating to see how Don Sweeney tries to keep this high-end band together with limited resources at his disposal.

Buffalo Sabres: Victor Olofsson (RFA)

The Buffalo Sabres are sort of in the same boat as the Coyotes. They aren’t in the process of tearing everything down and are a few steps further along in the rebuild process. Not to the point where they have a lot of difficult choices to make with regards to free agents, though.

We see Victor Olofsson as the trickiest situation general manager Kevyn Adams will need to navigate during the offseason. The rest of the UFAs who are in place could likely be kept for modest raises; Olofsson’s circumstance is a bit different.

His output this season had some pundits calling for Buffalo to trade him ahead of the trade deadline. Olofsson has hung around as one of the team’s top five or six scorers for a majority of this season, but his two-way impacts aren’t particularly great.

The former seventh-round pick’s cap hit was already just north of $3 million this season; just how much money and term will Adams be willing to spend to keep a one-dimensional winger? Olofsson is an important part of Buffalo’s developing identity, however, which could add another layer to these negotiations.

Calgary Flames: Johnny Gaudreau (UFA)

The Calgary Flames have 12 players entering some form of free agency this summer. It’s going to be a career-defining stretch of time for GM Brad Treliving, and if it doesn’t turn out to be that, then it’s not a stretch to say that this offseason will define his time in Calgary.

The choices he makes in the coming months will echo through the next decade-plus for the Flames, and it all starts with Johnny Gaudreau. He’s arguably the best left wing in the NHL and an assertion can be made that he ought to be a finalist for the Hart Trophy this season.

He’s on pace for 114 points and 40 goals; both of which would represent career highs for Johnny Hockey. Put another way: He could end up scoring more goals in 2021-22 than he did over the last two campaigns combined (37 goals in 126 games).

This is why Gaudreau will be such a tough negotiation for the Flames. If he wants to get paid like a 100-plus point player, there will be a team willing to give him his bag. The fact remains, though, that in three of his nine seasons he’s failed to score at least 20 goals—including 2019-20 and 2020-21.

Prior to this year, the diminutive forward had only broken the 80-point barrier two times, and that was during his age-24 and age-25 seasons. Gaudreau will be 29 when the next campaign begins, meaning that an eight-year commitment could be a massive mistake by Treliving.

Maybe there’s a middle ground that the player and team can reach. The GM certainly seems to believe that a deal will get done, but this is a situation that could get sticky in a hurry if Gaudreau tries to get Connor McDavid or Auston Matthews money.

Carolina Hurricanes: Tony DeAngelo (RFA)

By re-signing Jesperi Kotkaniemi to an eight-year, $38.56 million contract extension in March, Carolina Hurricanes general manager Don Waddell handled his most intricate situation before the offseason even rolled around. And good on him for doing so.

This is still a team with numerous free agents to deal with, however. Even though they have a few everyday forwards hitting free agency, their talks with Tony DeAngelo will still be the most complicated.

We’d hear arguments that discussions with Vincent Trocheck will be more tricky, but it is almost a foregone conclusion at this point that he’ll be hitting the open market. The 29-year-old Nino Niederreiter may also not be in Carolina’s long-term plans.

DeAngelo, 26, could very well be, though. He signed a bargain-basement $1 million contract with the Hurricanes this past summer, and the move drew backlash at the time. The Rangers bought out DeAngelo’s contract last July after an altercation with a teammate earlier in the 2020-21 season. He was also suspended twice during his time in the OHL, once for breaking the league’s policy on “homophobic, racist and sexist language.” The defenseman has managed to keep his head down in Carolina, though, perhaps saving his professional hockey career in the process.

He’s on pace to score more than 50 points this year, however, and defensemen like that can get paid if they want to. Will Waddell commit dollars and term to DeAngelo, acknowledging how important he’s been to the team’s blue line? Or will DeAngelo price himself out of a range that the Hurricanes are comfortable with?

The fit here seems to be fantastic, so we’ll see where this one goes.

Chicago Blackhawks: Dylan Strome (RFA)

The writing seems to be on the wall for the Chicago Blackhawks: Changes are coming, and some of them could be big. New general manager Kyle Davidson may have tipped his hand a bit by seeming to go out of his way to keep one of his retained salary slots open at the trade deadline.

If the Blackhawks decide to move on from Jonathan Toews, who would be eligible to become a UFA next summer, they’d need someone capable of stepping up and playing as a top-six center. This is where Dylan Strome comes in.

There were some rumblings that the pivot could be moved at the deadline. That deal never materialized, however, and Strome is now the most tricky negotiation that Davidson will have to deal with this summer.

The 25-year-old was perpetually in former head coach Jeremy Colliton’s doghouse but has played much better under Derek King. He’s still just the interim coach, though. If Chicago sees him as the Strome whisperer but doesn’t intend to keep the bench boss around long-term, then signing the forward to a longer-term deal might not make a lot of sense.

It seems like the best route here would be a prove it deal, allowing Strome to show that he can skate as a top-six center for an entire season, and not just when a new coach finally gives him an opportunity to do so.

Colorado Avalanche: Nazem Kadri (UFA)

Nazem Kadri’s situation isn’t entirely dissimilar to Gaudreau’s in Calgary. Entering this season, we thought we had a pretty clear idea about the kind of player Kadri is. This is his 10th season as an NHL regular, and leading up to 2021-22, there wasn’t a reason to believe he’d score more than 30 goals and push the 100-point barrier.

He was three seasons removed from his last 30-plus goal campaign, and Kadri had never scored more than 61 points in a year, let alone 100.

It should be pretty clear which Kadri is the real Kadri, but there’s no way to overstate how important he’s been to the Colorado Avalanche in 2021-22. As the team’s top players continue to cycle in and out of the lineup with various injuries, the veteran center has managed to stay mostly healthy and productive.

Players like Kadri are important to Stanley Cup contenders; being able to ice someone who is outplaying his cap hit to a ridiculous extent is a nice luxury to have. If he’s looking to cash in on his career year entering his age-32 season, though, odds are good he’ll have to do it elsewhere.

General manager Joe Sakic has his hands full with numerous negotiations this summer, and a few of them won’t be easy. Kadri represents the biggest challenge to the Avalanche GM, though. Overpaying him for what he did in 2021-22 would be a misstep, but undervaluing what he’s meant as a middle-six skater would be one too.

Columbus Blue Jackets: Patrik Laine

For the Columbus Blue Jackets, keeping talent in place has proven to be a real chore over the last few seasons. From Sergei Bobrovsky to Artemi Panarin to Pierre Luc-Dubois to Seth Jones, the organization has had a hell of a time convincing high-end skaters to spend the majority of their primes in Ohio.

This is why re-signing Zach Werenski in July was so important to the franchise and the fans who cheer for the Blue Jackets.

Enter Patrik Laine, who had a lot to prove this season after a mediocre campaign in 2020-21. And prove it he has, too. Just not exactly the way he may have wanted to. The wing has always had the reputation of being a streaky goal scorer, and that has shown through this year.

From Jan. 30 to March 19, only Auston Matthews scored more goals than Laine’s 19 across a 22-game stretch that saw him post 31 points in total. Prior to that run, however, he’d found the back of the net just five times in 20 games.

There were off-ice situations that contributed to that cold streak, to be certain, and it’d be unfair to ignore that part of the equation. Since March 19, though, Laine has gone nine games without lighting the lamp. Given those inconsistencies, and that the 23-year-old is a defensive sieve, and his GSVA shakes out to be just over one. His offense is in the top 10 percentile while his defense is in the bottom 10 percent.

Players who earn more than $8 million a season generally have greater on-ice impacts than that. Given that Laine is an RFA who made $7.5 million in 2021-22, the Blue Jackets will have their hands full with these negotiations.