Every NHL Team's Toughest Free-Agent Decision

Franklin Steele@SteeleOnIceFeatured Columnist IIIApril 10, 2022

Every NHL Team's Toughest Free-Agent Decision

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    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)

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    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)

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    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)

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    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)

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    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)

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    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)

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    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)

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    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)

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    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

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    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.

Dallas Stars: John Klingberg (UFA)

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    Against a lot of odds, the Dallas Stars have been in contention for a playoff spot for the majority of this season. They have gotten some help from the underachieving Vegas Golden Knights, but hey, they play the games for a reason.

    This postseason push is why general manager Jim Nill hung onto defenseman John Klingberg even though he could have received a King's ransom for the pending UFA skater. Even though Nill has made it pretty clear that he has no desire to give the 29-year-old the kind of contract he is reportedly after. And the blueliner is on the record with how unhappy he has been with said negotiations.

    So yeah, it's fair to characterize these discussions as difficult. The Stars are a one-line team that is getting dragged, kicking and screaming, into the playoffs by a great first line. There's a steep drop off after that, however.

    Head coach Rick Bowness has more or less stuck with his line combinations, with three units clocking in with more than 200 minutes played together. That's a lot of consistency—consider that three teams in the NHL don't have a single unit with 200-plus time on ice together—and it allows us to understand that when Roope Hintz, Joe Pavelski and Jason Robertson aren't on the ice, Dallas doesn't look like a playoff team.

    If you're Klingberg, is this a situation you want to re-sign into? And if you're Nill, why don't you want to keep a defenseman who you deemed too integral to your playoff chances to trade, but won't commit to him long term?

    This is a strange scenario, and it seems like we know how it'll end.

Detroit Red Wings: Filip Zadina (RFA)

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    When Filip Zadina slid to the Detroit Red Wings at the 2018 draft, he told Helene St. James that "I was telling my agent, if they will pass on me, I'm going to fill their nets with pucks. I want to prove to Detroit that they make a pretty good decision."

    At the time, Zadina was expected to go as high as second overall. He fell to the Red Wings at No. 6, and four years later, he hasn't even lived up to that draft billing. Now general manager Steve Yzerman has a complicated, but fascinating, decision to make.

    For a player who was billed as a goal scorer, Zadina has done virtually none of that during his time in the NHL. This season should be the first that sees him find the back of the net more than 10 times, but not even that is a guarantee.

    All told, he's barely scored more than 20 times in his first 150-plus games in Detroit. If Yzerman believes Zadina, who was selected by former GM Ken Holland, still has another gear or two and will settle in as a 25-plus goal-a-year guy, then he could lock him in at a low cap hit now and reap the benefits later.

    Or the Red Wings could give Zadina a small extension, ask him to prove it, only to see him do so and have to pay up in a year or two. And, of course, we could see the 22-year-old moved to an organization that believes a change of scenery would do him good. It's not like he's been surrounded by elite talent in Detroit. 

    This isn't a make-or-break situation for Yzerman, but it's certainly the most difficult free agent scenario he's dealing with internally.

Edmonton Oilers: Mikko Koskinen (UFA)

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    Mikko Koskinen's relationship with Edmonton Oilers fans has been complicated. Signed by former general manager Peter Chiarelli during his last handful of teams running the organization, the netminder has struggled to live up to his billing as a high-end No. 1 goalie.

    Now in the final year of his contract, GM Ken Holland will need to decide whether he wants to give the 33-year-old netminder another shot in Edmonton. Barring a lights-out run to the Stanley Cup Final—or something along those lines—this call will place a lot of pressure on Holland and Co.

    To this point, the Oilers haven't won much of anything since drafting Connor McDavid. There's plenty of blame to go around, but over the last three years, it'd be fair to say that Koskinen has struggled. He's been better as of late, but that isn't saying much when he's struggled to be above replacement level in the past.

    Since Jan. 1, 44 goalies have appeared in at least 15 games. Koskinen's all situations save percentage of .902 is good for 29th on that list. The Oilers aren't exactly flush with cap space, however, and the list of free-agent goalies isn't particularly impressive.

    This all leaves Holland and Co. with a tough choice to make in whether or not to keep Koskinen in Edmonton.

Florida Panthers: Ben Chiarot (UFA)

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    With the Montreal Canadiens, Ben Chiarot was one of the most divisive players in all of hockey. Through the strict lens of analytics—which should never be used to paint the entirety of a player's picture—the defenseman isn't particularly good.

    The Habs were generally better when he was off the ice than when he was on it, and it was fair to call his usage as a No. 1 defender into question. But the 6-foot-3, 234-pound blueliner is zero fun to play against, meaning that more old-school hockey viewers liked his style.

    Since being traded to the Florida Panthers, Chiarot has settled in wonderfully alongside the underrated and steady MacKenzie Weegar. He's also spent time on a pairing with Radko Gudas, which isn't a duo any opposing player is going to want to play against throughout a playoff series.

    Florida won't have a ton of cap space to play with, but the fit has been so good, one has to wonder if Chiarot, at 30 years old, would be willing to take a bit of a pay cut to chase Stanley Cups for the next half-decade with the Panthers. Where it should be noted, there is no income tax.

    General manager Bill Zito could also offload a contract like Patric Hornqvist's, creating the space needed to keep his trade deadline acquisition in the lineup for the next few seasons.

Los Angeles Kings: Alexander Edler

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    Far from the biggest name on this list, Alexander Edler is still an integral part of the Los Angels Kings' blue line. The organization doesn't really have any overly important negotiations to handle this summer, but whether to bring back the defenseman will be the toughest choice general manager Rob Blake has to make.

    The Kings have a handful of potentially elite defensemen in their prospect pipeline, ranging from 2021 eighth-overall pick Brandt Clarke to Helge Grans, who was selected with the 35th selection in the 2020 draft. The catch is that almost all of their high-end defensive prospects shoot right.

    Edler is a lefty and is a veteran of more than 950 regular-season contests. Over at HockeyRoyalty.com, Pavel Maliouguine recently characterized Edler as arguably "the most under-appreciated player on the entire roster," and odds are good that he could be re-signed at a fraction of his current $3.5 million cap hit.

    This isn't a make-or-break choice for Blake, but he will have to decide whether or not he values an open roster slot more than Edler's steady presence on the back end.

Minnesota Wild: Kevin Fiala (RFA)

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    As things stand right now, the Minnesota Wild won't be able to afford to re-sign Kevin Fiala. Over at The Athletic, Dom Luszczyszyn's model places the forward's market value at $9.4 million. With nearly $13 million in dead cap space following the buyouts of Zach Parise and Ryan Suter, Minnesota has less than $9 million in cap space total, with six current roster players in need of new deals.

    Even operating under the assumption that deadline pickup Marc-Andre Fleury is just a rental, general manager Bill Guerin will have his hands full trying to figure out how to keep the top-six forward in the fold.

    The Wild may have already tipped their hands when it comes to their plans for Fiala. During a mailbag in mid-March, longtime Minnesota scribe Michael Russo of The Athletic was asked about the forward's future with the club and had this to say: "There is no chance the Wild can afford Fiala now that they’ve extended Greenway, Jon Merrill and added Jost, unless they plan to trade Matt Dumba or one of those players or someone else."

    Russo noted that it was "telling" that Guerin had prioritized these other moves instead of re-signing Fiala, so maybe this won't be a difficult choice at all. Maybe it's already been made. Still, this is the biggest bit of offseason business the Wild will need to handle when it comes to their free agents.

Montreal Canadiens: Rem Pitlick (RFA)

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    The Montreal Canadiens, who aren't as good as their Stanley Cup run a year ago would have you believe, but aren't as awful as they've been in 2021-22 either, don't have a particularly complicated offseason ahead of them.

    General manager Kent Hughes navigated the trade deadline impeccably, delivering what has been characterized as a "master class" by pundits around the team. It could have the Habs in a position to reload, especially if Carey Price is able to return to action and be effective.

    With a core mostly intact for the foreseeable future, Hughes will need to evaluate just where skaters like Rem Pitlick fit in. He was claimed off of waivers for the second time in his career and has turned into a top-line option in Montreal.

    He's clicked on a top line alongside youngsters Nick Suzuki and Cole Caufield, drawing praise from the latter for his playmaking ability and vision. "He's been unbelievable for us ever since he got here," Caufield said earlier in April, according to NHL.com. "To have a playmaker like that, he sees the ice really well and kind of sees things before they happen, so it'll be really nice to play with him and hopefully we can find each other."

    Sounds like the kind of found money that Hughes would be wise to keep around for the next few seasons.

Nashville Predators: Filip Forsberg (UFA)

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    Nashville Predators general manager David Poile has seen it all during his days in the NHL. Yet the situation he's put himself in with pending UFA Filip Forsberg isn't an enviable one. After deciding not to move the 27-year-old at the trade deadline, the Predators are now in a spot where they essentially have to back a Brink's truck up to the forward's driveway and hope it gets the job done.

    As Gentry Estes of the Tennessean wrote following the deadline: " ... Poile no longer has a choice. Since he didn't trade Forsberg, he must re-sign him. Period."

    Estes is spot on in his reasoning, and you know Forsberg and his camp are aware of the fact that they have Nashville over a barrel. Luszczyszyn's model values the center at north of $11 million. The Predators have more than $27 million in cap space to work with, but will Poile be willing to shell out more than $10 million a season to keep Forsberg on the roster?

    One has to assume that if an eight-year extension worth more than $80 million had been tabled, there wouldn't be a discussion to be had here. These negotiations will be difficult, and it's not hyperbole to say that the Predators' immediate future hinges on them.

New Jersey Devils: Jesper Bratt (RFA)

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    Jesper Bratt's situation differs from the likes of Morgan Frost and Filip Zadina because he's already a star for the New Jersey Devils. He's established himself as part of a core that could look dramatically better as early as next season, and GM Tom Fitzgerald will have his hands full trying to figure out just how to structure his offers to the 23-year-old wing.

    New Jersey has the cap space to do pretty much whatever it wants to do with regards to Bratt. Fitzgerald can also point to captain Nico Hischier's $7.25 million cap hit and say, "OK, no one is making more than that." That might be a tough sell to Bratt, though.

    He's quietly on pace to push 30 goals and surpass 70 points this year. With Hischier locked up until 2027 and breakout star Jack Hughes until 2030, the Devils have a real opportunity to lock in a quality core at cap hits that will likely age well.

    Bratt figures to be a part of that group, so it's just a matter of whether or not Fitzgerald wants to buy up some of the forward's UFA years after it took the former sixth-round pick half a decade to put it together at the NHL level.

New York Islanders: Noah Dobson (RFA)

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    New York Islanders general manager Lou Lamoriello already took care of the super pressing need to re-up veterans Zach Parise and Cal Clutterbuck, leaving small fish like Noah Dobson left to handle. Read: re-signing Parise and Clutterbuck wasn't all that pressing, and the focus probably should have been on getting the blueliner locked in first.

    The former 12th-overall pick is in the midst of a breakout campaign, already having nearly twice as many points this season (40) as he did in his rookie and sophomore seasons combined. Lately, we've seen organizations skip bridge deals entirely for their emerging offensive defenseman, securing them into long-term, big-money contracts as soon as they can.

    Adam Fox, Charlie McAvoy and Cale Makar are examples of skaters who skipped the bridge deal entirely, committing to their franchises for the foreseeable future.

    Will Lamoriello follow the pack and get Dobson to stick around on Long Island for the next five or six seasons? If anyone would push back against new ways of doing things, it's Lou, so these negotiations will be an interesting litmus test for the old-school GM.

New York Rangers: Ryan Strome (UFA)

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    Playoff success—or failure—could define the New York Rangers' offseason. If someone like Ryan Strome or Andrew Copp plays a large part in a run at the Stanley Cup, it'd be much more difficult for general manager Chris Drury to allow either play to depart via free agency.

    Strome has been in New York for four seasons and has firmly established himself as the No. 2 center behind Mika Zibanejad (who will see an eight-year extension worth $68 million kick in next season) while developing outstanding chemistry with Artemi Panarin.

    How much those roles are worth will be difficult for Drury as he tries to navigate the Rangers towards being consistent contenders. The Blueshirts have leaned heavily on otherworldly efforts from goaltender Igor Shesterkin this season but don't look like the same club when he's not playing well.

    It'd be easier to let Strome walk if former 2017 first-rounder Filip Chytil had evolved into a top-six pivot by now, but he hasn't gotten there yet. He's been good for New York playing on a more sheltered third line, but the idea of promoting him to the second unit might not be a particularly good one for now.

    That makes negotiations with Strome all the more important. He could possibly fetch a payday worth around $7 million if he hits the open market, which might be a bit too rich for Drury and Co.

Ottawa Senators: Chris Tierney (UFA)

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    The Ottawa Senators might have a busy summer, but it won't be because they're clamoring to re-sign unrestricted free agents. They only have one on the docket—Chris Tierney—along with a handful of other more low-key RFAs to deal with.

    Tierney was involved in trade rumors leading up to the deadline, but ultimately, the Senators chose to hang onto the 27-year-old center. Next season looks like another one spent in rebuild mode for Ottawa, but someone has to take on those top-six minutes without breaking the bank.

    Tierney fits that bill for the Senators, and it isn't like he'll be due a noteworthy raise after his four-year stint with the Senators. Josh Norris is coming along just fine, Tim Stutzle was drafted third overall in 2020 to play center, and Shane Pinto, 21, appears to be a solid pivot too.

    This is a young but promising group in Ottawa, and there might not be room on the roster for Tierney as the Senators try to get as much ice time as possible for their developing players.

Philadelphia Flyers: Morgan Frost (RFA)

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    By trading away Claude Giroux, the Philadelphia Flyers have already made their most difficult free-agent decision. The former captain is now tearing it up for the Panthers and has settled in nicely on the Stanley Cup contender.

    That leaves general manager Chuck Fletcher a handful of negotiations to navigate, but the talks with Morgan Frost could prove to be the most difficult. Like a few other players on this list, how the Flyers evaluate the former first-round pick (27th overall in 2017) internally will determine the length of contract he receives.

    Philadelphia could decide to ink the center to a longer, more team-friendly deal if the belief is that he still has some game to grow into. Fletcher could also choose to go the "prove it" route by signing him to a bridge contract that wouldn't eat up any UFA years.

    Situations like this can generate a ton of value for clubs that have their finger on the pulse of their own player development. However, whiffing can lead to a lengthy contract for a player who isn't playing important minutes. Frost has spent time in the minors this season but knows he has to be better to stick at the NHL level.

    Since the season rolled over to 2022, Frost has scored just once and added four assists. Six points in 32 games don't exactly scream "buy up some of my UFA years," and at 22, he may be running out of runway as a potential top-line mainstay.

Pittsburgh Penguins: Evgeni Malkin (UFA)

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    The idea of Evgeni Malkin hitting free agency is an odd one. While there was pressure on teams like Nashville to trade high-end pending UFAs like Filip Forsberg at the deadline, the Pittsburgh Penguins didn't feel the same heat.

    Geno didn't find his way on to any deadline big boards and wasn't involved in any legitimate trade rumors leading up to March 21. Malkin is almost as synonymous with the Penguins as Sidney Crosby is, and at 35, the idea of him playing elsewhere seems strange.

    Still, if the veteran center comes to the table and isn't willing to take a pretty substantial pay cut from the $9.5 AAV he's had since 2014, then things could get tricky for Pittsburgh. It's true that Malkin is still a point-per-game talent when healthy, but staying out on the ice has proven difficult for the center in recent years.

    There'd be a team willing to pay for a sometimes-healthy-sometimes-not Malkin, though, as he's still a tremendous player and could be a No. 1 pivot on at least a third of the teams in the NHL. This will be a challenging balancing act for general manager Ron Hextall to pull off.

    Hextall already noted earlier this year that if players want the biggest payday possible, they'll likely need to go elsewhere to find it. Just something to keep in mind in the coming months if you're a Penguins fan.

San Jose Sharks: Alexander Barabanov (UFA)

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    When the San Jose Sharks decided to re-sign Tomas Hertl, they were handling their most complicated bit of free-agent business by far. We can look at that choice and figure out now that there's no appetite for a tear-it-down rebuild in California, which leads directly to Alexander Barabanov and his future in San Jose.

    The Hertl extension had barely been announced before fans and pundits alike started wondering about whether or not the Sharks would be able to hang onto the potential unrestricted free in Barabanov.

    San Jose has some massive deals still on the books, leaving it with virtually no cap space to work with if the 27-year-old decides to seek the biggest payday possible. One could even argue that his play as of late has priced him out of the conversation entirely.

    This franchise isn't just going to let a skater like this walk, though. Especially not now that they seem committed to winning as much as possible over the next few seasons. Barabanov has established himself as an important cog in San Jose, and figuring out how to maintain his services will be paramount for this club during the offseason.

Seattle Kraken: Haydn Fleury (RFA)

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    Few teams in the NHL feature fewer leaks than the Seattle Kraken. General manager Ron Francis is running one of the most tight-lipped management circles in the league these days, so it's difficult to get a read on the organization when it comes to just about anything.

    Still, there aren't many free-agent issues that Francis and Co. are staring down heading into this offseason. He traded away most of his bigger-named pending UFAs at the trade deadline and is clearly taking the draft-and-develop path towards contention.

    Still, seeing how Seattle evaluates a defenseman like Haydn Fleury will give us some insight into their player evaluation process. This is a 25-year-old blueliner with an offensive skill set who just hasn't seemed to find his footing at the NHL level.

    We've seen players like him pop off a bit later than expected, though. Locking him into a small cap hit on a longer-term deal represents an interesting gamble for the Kraken—one that, due to a sheer lack of other competitors for the title, is the team's toughest free-agent choice this summer.

St. Louis Blues: Ville Husso (UFA)

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    On the surface, it looks like the St. Louis Blues have dealt with a bit of a starting goalie controversy this season, but that hasn't really been the case. Since November, Ville Husso has flat out been better more consistently than Jordan Binnington, so while the former might not have a No. 1's contract, he's earned the starting job for the playoff-bound club.

    If the postseason started today, there's really no question about who'd be starting Game 1. It'd be Husso, despite Binnington being in the first season of a six-year pact worth $36 million. That deal also contains a full no-trade clause until 2024.

    Projecting value for netminders is hard—Bennington is actually a case-in-point here—but there's no doubt that Husso has outplayed his $750,000 cap hit. He is eligible to enter free agency this summer, and with a market that is looking shallow when it comes to starting-caliber netminders younger than 30, he could be able to cash in.

    Allowing one of the best goalies in the NHL during the 2021-22 season to walk for nothing would be tough for general manager Doug Armstrong. One has to think that he'd like to keep the goalie around after he took and then kept Binnington's starting job.

    Just how much Husso believes he's worth after one stellar campaign will be the driving factor in play here.

Tampa Bay Lightning: Ondrej Palat (UFA)

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    Once regarded as a core member of the Tampa Bay Lightning, Ondrej Palat may not be a part of the organization's future. His five-year deal worth $26.5 million is coming off of the books at the end of this season, and it's tough to find anyone who's actively talking about bringing the forward back.

    In the summer of 2023, the Lightning will have to worry about locking up their next wave of talent in Mikhail Sergachev, Erik Cernak and Anthony Cirelli. Tampa Bay will likely look to stay away from more long-term commitments until it can lock in deals with that important trio.

    That leaves general manager Julien BriseBois, one of the shrewdest in the sport, a few options. One on hand, he could try to sign a veteran or two with the cap space he will have available for one season. Skaters like Phil Kessel and Paul Stastny are potential fits.

    BriseBois may also be able to get a hometown discount from Palat, which might make sense for the player since Tampa figures to be contenders for several more seasons. It'll boil down to what is most important for the 31-year-old, who has the Stanley Cup acumen and enough scoring pedigree to be valuable on the open market.

Toronto Maple Leafs: Jack Campbell (UFA)

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    As mentioned earlier, the free-agent market won't feature many established quality netminders. There are some gambles to be had, but there aren't many sure-fire No. 1 goalies available. 

    Because of this, Jack Campbell has put himself in the position to make a lot of money as a free agent.

    The Toronto Maple Leafs also aren't in a position where they can afford to lose him. Petr Mrazek will still be under contract, but he's less than one month removed from being waived by the organization. Not exactly an endorsement in their belief of him as a possible No. 1 goalie for next season.

    Toronto needs to bring back Campbell. Again, there are no viable replacements for him available as free agents. The issue is that the Maple Leafs might not be able to match the goalie's market value if he's attempting to land his first big payday as a free agent.

    He will hit the cap for more than the $1.65 million he did in 2021-22. The big question in Toronto, then, will be whether or not the Maple Leafs have the stomach to triple that cap hit while carrying Mrazek at $3.8 million too.

Vancouver Canucks: Bruce Boudreau

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    With all due respect to Brock Boeser—who is presenting the Vancouver Canucks with a conundrum of sorts as an RFA—convincing head coach Bruce Boudreau to return for another season is the most difficult and most important aspect of this offseason for general manager Patrik Allvin.

    The point has been beaten into the ground, but the indisputable fact remains that the Canucks have looked like a different team since the veteran bench boss took over in early December. Odds seem good that if he'd been at the helm all year, Vancouver would have been able to compete for a playoff spot in the Western Conference.

    They'll fall just short of that accomplishment this season, but there's a lot of reason to be optimistic about the squad heading into 2022-23. This is why getting Boudreau back behind the bench is integral to the team's success moving forward.

    Vancouver has the option to hang on to Boudreau. There's no reason for Allvin to galaxy-brain a choice that should be simple, but until we know for sure, this will be the biggest choice that the Canucks need to make this offseason.

Vegas Golden Knights: Reilly Smith (UFA)

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    At one point, Reilly Smith embodied everything that the Vegas Golden Knights were all about—a group of ragtag underdogs who were undervalued and cast off by their old clubs at or around the expansion draft. The forward erupted for 60 points during Vegas' inaugural season before notching 22 points in 20 playoff games during the Golden Knights' improbable run to the Stanley Cup Final.

    A lot has changed in Nevada since then. General manager Kelly McCrimmon has developed an almost reckless tendency to pursue every star player possible, leaving the Golden Knights, when healthy, way, way over the salary cap.

    That likely means the end of Smith's time with Vegas, but that'll still be a difficult choice for the GM to make. Smith personifies an identity that the Golden Knights have gotten away from and struggled to win since.

    It seems likely that McCrimmon will need to shed some dollars to get cap compliant for the 2022-23 season. Would he be able to (or willing to) carve out enough space to hang onto Smith? It's difficult to see how it's possible, but the Golden Knights have been doing cap-space gymnastics all season long. Who knows what kinds of tricks they have up their sleeves at this point.

Washington Capitals: Ilya Samsonov and Vitek Vanecek (RFAs)

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    We're just a few weeks away from the Stanley Cup playoffs, and Washington Capitals head coach Peter Laviolette is still waiting for one of Ilya Samsonov or Vitek Vanecek to seize the starting job. That's not exactly an enviable position for the club to be in as they try to make the most out of Alex Ovechkin's twilight years as a walking highlight reel.

    Neither has established themselves as clear-cut starters, making the upcoming negotiations with them even more difficult. If a clear pecking order existed, it'd be easier for the Capitals to commit dollars and term to one while perhaps trading the order.

    Both goalies have shown flashes this season, but neither has had stretches long enough (or consistent enough) to become the de facto No. 1. Vanecek appeared to have the job locked down before a recent skid, and now Washington is pretty much back to square one on the goaltending front.

    This is another situation where internal player analysis will play an important role in deciding who gets what kind of money. With both goalies playing inconsistently on expiring contracts, though, this could be an intriguing summer for Washington's crease.

Winnipeg Jets: Pierre Luc-Dubois (RFA)

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    Pierre Luc-Dubois and the Winnipeg Jets have a few options available to them.

    Legit star centers are difficult to come by, so this is a player that general manager Kevin Cheveldayoff would likely prefer to build around. You hear about rebuilding teams such as Detroit badly needling to find and draft one for a reason.

    However, Dubois qualifies for unrestricted free agency as early as 2024, meaning he could have his pick of destinations while also taking home a massive check (assuming his game doesn't plummet for some reason). Winnipeg already went to the wire with Andrew Copp and ended up trading him to the New York Rangers.

    For the Jets to compete, retaining skaters like Luc-Dubois is an absolute must. Winnipeg has locked up the likes of Kyle Connor and Josh Morrissey to long-term commitments, so it wouldn't be surprising to see the Jets offer Luc-Dubois an even bigger extension to stick around in Winnipeg for the next five-plus seasons.

    This is still a player who's already forced his way out of one organization, though, and until the ink dries on a new deal, that possibility will always loom.

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