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When it comes to drama around contract negotiations with restricted free agents, nothing will touch the summer of 2019.

That year, young stars like Mitch Marner, Matthew Tkachuk, Kyle Connor, Patrik Laine, Brayden Point, Charlie McAvoy and Mikko Rantanen required new contracts coming out of their entry-level deals.

It was a tense landscape, with teams and agents deploying brinkmanship tactics to squeeze out the best possible deals. As a result, all of the players listed above ended up signing contracts after Labor Day, with multiple young stars actually missing the start of training camp. This summer we certainly don’t have the same star power in the RFA class, but there are still a handful of prominent young players who need to sign new contracts. Here is a look at seven key RFAs and whether we envision them signing shorter bridge deals or long-term contracts — depending on the situation of the team and the individual player.

(All team salary cap figures courtesy of CapFriendly. And Evolving-Hockey’s projections are in place of actual contracts for all RFAs pictured)

Still in the heart of a rebuild, no team in the NHL has as much cap space to play with as the Anaheim Ducks. Their projected payroll for the 2023-24 season is currently expected to come in just north of $64 million — leaving them with more than $19 million of room. However, a good chunk of that will be eaten up by the deals they need to sign for their two budding young stars.

Up first is Zegras, one of the most dynamic and entertaining young players in the game. He has posted consecutive 23-goal seasons in his first two full campaigns in the league, with many of those goals — and his slick assists — ending up on highlight reel clips on social media. As one of EA Sports’ “NHL 23” cover athletes, Zegras is often viewed as one of the faces of the next generation of young stars. But in negotiating this contract, Ducks general manager Pat Verbeek will be less inclined to factor in Zegras’ immense popularity as a marketing tool and more likely to stick to his projected impact on the ice in Anaheim.

As Eric Stephens wrote earlier this month, Verbeek must decide if he believes Zegras can emerge as a dominant, Jack Hughes-type of centreman. If the answer is yes, then locking him up to a maximum-term extension probably makes a lot of sense right now, before Zegras explodes for a season that pushes beyond the point-per-game threshold. That would line up with Evolving-Hockey’s highest probability projection of an eight-year deal, carrying a $8.49 million cap hit. But as Stephens pointed out, Verbeek has yet to hand out an eight-year term to anybody since taking over as general manager in Anaheim. He didn’t do it for Troy Terry or Hampus Lindholm. Would he consider going maximum term for Zegras? And should he, considering the likely associated cap hit with a contract of that length? It’s a deal that would exceed his market value unless he takes his game to the next level in his prime.

But if you’re Zegras and his agent Pat Brisson, would you rather settle on a shorter-term bridge deal now and wait for the salary cap to rise in a couple of years? In theory, that could net Zegras a bigger payday if he hits his offensive ceiling.

This could certainly be one of the more fascinating RFA contract negotiations, just given the season-ending injury Drysdale sustained in October last year. A torn labrum in his shoulder limited the No. 6 pick from the 2020 NHL Draft to only eight games in 2022-23.

The previous season, however, Drysdale appeared in 81 regular season games for the Ducks and logged nearly 20 minutes of ice time per night. A coveted right-shot defenceman with a high offensive ceiling, Drysdale has the potential to be the quarterback of the Ducks power play for the next decade. But in his brief 113-game sample in the NHL, Drysdale has yet to cement himself as a defender who can play in all situations.

He has logged fewer than 30 total minutes of short-handed ice time in his NHL career, which comes in at roughly 15 seconds per game. Other young defensemen drafted in similar spots like Moritz Seider and Jake Sanderson have established themselves as consistent penalty-killing options for their respective teams, so Drysdale’s camp may have a tricky time finding a good comparable.

Evolving-Hockey projects a short-term contract for Drysdale that comes in at around $1.85 million a year for the next two seasons. That would slide below his current market value (of $3.3 million per year, on average, between the next two years), but give the defenseman a chance to pump up his earnings with more playing time ahead of his next negotiations.

The No.1 pick from 2020 certainly isn’t going to be the highest-paid player from his draft class. That distinction belongs to Tim Stützle, who is about to start an eight-year deal that comes with an $8.35 million AAV.

Lafrenière has not been able to gain the same offensive traction as Stützle, even though he’s only missed a grand total of four games over the course of his three full seasons in the NHL. The Rangers have given him ample opportunity, but Lafrenière has yet to prove that he’s a productive top-six forward.

Whereas other recent No. 1 picks like Hughes, Nico Hischier and Auston Matthews have hit home runs on their second contracts coming out of entry-level, Lafrienère appears poised to sign a modest bridge deal. As Arthur Staple wrote in a recent mailbag column, there doesn’t seem to be a ton of urgency to get anything done with Lafrenière, who is most likely looking at a one or two-year contract with New York.

The Rangers have just over $2 million in cap space with Lafrenière the only notable player without a contract for 2023-24. Considering the team’s cap situation, and the player’s slower-than-expected start to his NHL career, his next deal could come close to what Evolving-Hockey projects — a two-year deal worth $2.69 million. A long-term contract could come cheap, too, but obviously limits what the player could make down the line and may be too big of a risk for the Rangers to commit to since he hasn’t thrived yet. But to even reach the AAV associated with that two-year projection, which should be cost-effective over the next two seasons, New York would probably have to find just a bit more cap space.

In a way it feels strange that Bouchard is only coming off his entry-level contract, considering he made his NHL debut in October 2018. Bouchard has already suited up for 28 playoff games for Edmonton and he’s now firmly established himself as a top-four defenseman for the team.

But one of Oilers general manager Ken Holland’s hallmarks is he likes to let prospects marinate for an extra year or two. And thanks to the entry-level slide rule, the Oilers were able to postpone Bouchard’s second contract until this summer.

Bouchard had a breakout performance last spring for the Oilers, finishing with 17 points — the most of any NHL defenseman in the playoffs — despite the fact Edmonton was eliminated in the second round. The Oilers’ dominant power play didn’t skip a beat when Bouchard replaced Tyson Barrie after the trade deadline.

Earlier this summer, Allan Mitchell suggested that Bouchard could flirt with the 60-point plateau next season, which would put him among the most productive defensemen in the game. He should see significant playing time with either Mattias Ekholm or Darnell Nurse next season and if he’s quarterbacking the Oilers’ lethal power play, Bouchard has the potential to be one of the most impactful players on a Stanley Cup-focused team.

The Oilers have roughly $3.5 million in cap space for next season with all of their players signed except for Bouchard. Will that be enough space to get a deal done — or will Holland have to move around some pieces to make sure Bouchard can fit into the roster before the regular season starts?

It isn’t enough for a long-term deal. Evolving-Hockey projects a six-year contract, worth $5.36 million a year, on average. But Bouchard’s worth a lot more than that already. His market value — a number an RFA typically doesn’t come near — is $10.2 million a year, on average, over the next six years. A more realistic number, based on other RFA defensemen signings of his caliber, is probably in the $8 million range. So unless the Oilers get to work moving out money, a bridge deal could be the more likely solution. That, per Evolving-Hockey, could put him in the $3-4 million range, instead.

When the Ottawa Senators signed Vladimir Tarasenko to a one-year, $5 million contract this summer, it was generally applauded in the market. However, the deal also brought the Senators to the precipice of the upper limit of the salary cap, which is bad news for Pinto. The Senators currently have less than $900,000 in cap space for the upcoming season, which is certainly not enough money to get their young center signed to a new contract.

Last season, Pinto scored 20 goals for the Senators in his rookie season, showing flashes of the offensive upside and promise that prompted the Senators to use the No. 32 pick to draft him in 2019. After a serious shoulder injury derailed his 2021-22 season, Pinto returned last season and played an elevated role for Ottawa thanks to Josh Norris’ injury.

In an ideal world, Pinto would be slotted behind Norris and Stützle as Ottawa’s No. 3 center on the depth chart to start this season, but right the Senators simply don’t have the cap space to sign him. General manager Pierre Dorion is going to have to get creative in a hurry if he wants to ensure Pinto is signed before the start of training camp.

If Pinto comes in anywhere near Evolving-Hockey’s projection for him — a two-year contract worth $1.78 million a year, on average — the Senators don’t have to clear too much room for him. The team’s ideal 3C would likely bring positive value throughout those two seasons at that rate, buying himself time to show that he’s worth more and Ottawa the time to make space ahead of his next deal.

Frost is the oldest player on this list, a 24-year-old who was a first-round pick of the Flyers in 2017.

And in the six years since he was drafted, Frost’s career has been hampered by injuries and inconsistency. But things finally clicked for the talented center in the back half of last season. As Charlie O’Connor wrote in July, Frost produced at a 60-point pace in the latter portion of the 2022-23 campaign. And he seemed to slowly win over head coach John Tortorella, who was certainly skeptical of Frost in October and November of last season.

But there are still questions about Frost’s ability to be a productive member of the Flyers’ power play and whether his second-half surge was a mirage — or a glimpse into his potential. Frost remains a somewhat polarizing player in Philadelphia, but he’s clearly moving out of the stage of being labeled as a prospect.

Frost is the last remaining unsigned player for Daniel Briere and the Flyers, who have just under $3 million of cap space remaining. Given the questions about his caliber play, a short-term deal is the most likely solution. A two-year deal, worth $2.49 million is what Evolving-Hockey projects. And that seems fitting given his performance so far and the team’s cap situation.

The Minnesota Wild enter this season with almost $15 million dead cap space being allocated to Ryan Suter and Zach Parise. As a result, Wild general manager Bill Guerin is pretty close to the salary cap ceiling, with roughly $1.6 million of space available.

Addison has emerged as somewhat of a power-play specialist in Minnesota. Last season, he was the only Wild defenseman to log more than 200 minutes of power-play time and he generated 18 power-play assists. But after the team acquired veteran John Klingberg at the deadline, Addison saw his role diminish, and the 23-year-old did not suit up for a single contest during Minnesota’s six-game series loss to the Dallas Stars.

Minnesota’s remaining cap should be just enough to get Addison under contract. He only projects to be worth just above $2 million a year, on average, over the next couple of seasons. So his actual deal probably comes in below that, close to what Evolving-Hockey projects at $1.43 million. If the Wild want an even lower-commitment contract, then a one-year deal projects to come in around $1.22 million.

(Top photo of Trevor Zegras: Sean M. Haffey / Getty Images)

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