5 lingering questions entering the NHL offseason

The 2023 Stanley Cup has been awarded, and while the Vegas Golden Knights light up the strip in Sin City with what projects to be an all-time championship celebration, hockey fans are shifting their focus to the beginning of offseason transactions.

The draft, free agency, and plenty of trades await before the league truly settles down for the dog days of summer, and several pertinent storylines across the NHL require answers. With that in mind, here are five lingering offseason questions to chew on before the action gets underway.

Can Brad Treliving extend Auston Matthews?

Kyle Dubas' messy exit from the Toronto Maple Leafs' general manager chair and the impending hiring of Brad Treliving made major waves as the playoffs raged on, and now that the Cup has been dished out, the pressure on Treliving to lock up the face of his franchise is set to grow exponentially with each passing day.

Treliving called a new Matthews deal his top priority at his introductory press conference, and it's difficult to ignore the addition of Shane Doan - an Arizona icon and one of Matthews' childhood idols - to the front office as negotiations loom. Matthews stated he's keen on signing an extension before the puck drops on the 2023-24 campaign, but mutual interest isn't nearly enough to make a deal of this magnitude a walk in the park.

Treliving needs to do his best to establish a team-first culture that didn't seem to exist under the previous regime because even if Matthews signs, negotiations with William Nylander (2024 UFA) and Mitch Marner (2025 UFA) are right around the corner. Offering Matthews less than he thinks he deserves is a dicey maneuver because, in this instance, the player holds almost all of the leverage.

His full no-move clause kicks in on July 1, and the Leafs can't risk Matthews walking for nothing a year from now. The 2022 MVP and two-time goal-scoring king will undoubtedly push to be near Nathan MacKinnon's league-high $12.6-million cap hit regardless of term. But the Colorado Avalanche great signed for eight years - something Matthews already decided against coming out of his entry-level contract. Theoretically, Matthews could sign a three-to-five-year deal and have one more chance to cash in around 30 years old, which is well within his rights. But if that's all Treliving can get, his tenure will be off to a rocky start in the eyes of a restless fanbase.

How many blockbuster trades can we expect?

The unrestricted free-agent market this summer is underwhelming, to say the least. There's no headliner like many years past, and while the Canada Day festivities may lack fireworks, there's one pretty strong consolation prize for fans craving player movement this summer: trades.

There's already been a pair of notable deals with Ivan Provorov and Damon Severson landing in Columbus, and based on all the rumors flying around, more blockbusters await. Will the San Jose Sharks cash in on Erik Karlsson's historic season? Are the Winnipeg Jets going to gouge their long-standing core? Pierre-Luc Dubois and Connor Hellebuyck have already expressed their desire to find greener pastures, and the writing could be on the wall as well for veterans Mark Scheifele and Blake Wheeler.

The Ottawa Senators are fielding offers on two-time 40-goal winger Alex DeBrincat, same with the Washington Capitals and forward Anthony Mantha. Elsewhere, the Philadelphia Flyers are trending toward a fire sale, the Calgary Flames have a glut of key players entering the final years of their contracts, and cap-strapped teams like the Boston Bruins may need to sacrifice high earners in order to become financially compliant.

Free agency may not produce much of a frenzy, but there should be no shortage of exciting transactions this summer.

Who will cash in on weak free-agent market?

We've already established the lack of appeal within this year's crop of UFAs, but that won't stop front offices across the league from scouring the list of available players to find some hidden value or perhaps overpay to make a splash out of desperation. While there are no superstars available, there are plenty of recognizable names that'll be putting pen to paper, including Dmitry Orlov, Ryan O'Reilly, and Vladimir Tarasenko. Veterans like Patrice Bergeron, Jonathan Toews, and Patrick Kane are also unrestricted, but the threat of retirement and injuries loom over the future Hall of Famers.

None of the players above are feasible long-term options. Even this year's most productive pending free agent - Alex Killorn, and his 64 points - carries significant red flags as a 33-year-old with a ton of extra mileage from Tampa Bay's deep playoff runs over the years. So who out there's worth buying?

Below are some players we think have the best chances of walking away from the hoopla notably richer. Contract projections are courtesy of Evolving-Hockey:

These totals pale in comparison to some of the mega deals we've seen in recent years, but the lavish spending projects to be back on track in 2024 with an increased salary cap for a star-studded list of UFAs.

Can Sabres use cap space to take next step?

The Buffalo Sabres were one of the biggest surprises this past season, finishing one point outside the playoffs while boasting one of the league's most dangerous attacks. There's no question Kevyn Adams has built a group on the upswing, and with nearly $17 million in cap space available this summer and over $49 million in 2024, the Sabres have the ammunition to ascend into contender status sooner rather than later.

It's worth noting Buffalo only has nine players signed beyond next season, and a Rasmus Dahlin extension (he's eligible for one on July 1) will likely take up a significant slice of the pie. However, that shouldn't stop Adams from actively seeking improvements this summer, as defensive depth and goaltending are areas of need. Spending lavishly in a barren free-agent market shouldn't be the goal this year, but using a top-tier prospect pipeline to get better now is worth considering.

A veteran goalie like Hellebuyck or John Gibson, also rumored to be on the block, would be a terrific mentor for Devon Levi and a highly serviceable stopgap until the youngster is ready to take the reins. Buffalo ranked 29th in five-on-five save percentage last season and needs to improve immediately if it's serious about making the playoffs.

The Sabres have two blue-line cornerstones in Dahlin and Owen Power, but an extra reliable veteran or two on the back end could go a long way in reinforcing Buffalo's chances in a deep Atlantic Division. The Blues, Kings, and Bruins all have experienced blue-liners that may need to be offloaded this summer, and if there's no fit in the trade market, Adams could stir the pot and try his luck with an offer sheet for high-end talents like Vince Dunn or K'Andre Miller.

How aggressive will Daniel Briere get?

While the Sabres are among the teams on the upswing this summer, the Flyers are the headliners among squads headed in the opposite direction. Briere pulled off some tidy work in the three-team trade that sent Provorov to the Blue Jackets, and many feel the move is the tip of the offseason iceberg for the rookie GM.

Travis Konecny, Carter Hart, and Scott Laughton are all rumored to be getting significant attention from potential suitors, and dealing any - or all - of them could shift the Flyers' imminent rebuild into overdrive. None of the three have trade protection, and all come with contract control to further boost their value. Konecny is under contract for two more years at $5.5 million, Laughton's deal costs a modest $3 million until 2026, and Hart is an RFA after his contract expires next season.

Each player could fetch a first-round pick and a top-end prospect, at the very least. With two first-rounders in each of the next two drafts already, Briere could aggressively add to an enviable stockpile of future selections if he shops his most attractive trade chips leading up to this month's festivities in Nashville.

Shipping out three talented core players in short order may be difficult for Flyers fans to swallow, but the organization has lacked a long-term vision for years, and Briere has been presented with a golden opportunity to establish a roadmap to contention within his first year in the chair.