MATT LARKIN: I’ll go with Connor Hellebuyck. The Oilers have the greatest player of the last quarter century, the best power play in NHL history, multiple lines that can score, great team toughness and even a shutdown blueliner after adding Mattias Ekholm at the trade deadline. What’s missing? Starting goaltender Stuart Skinner got pulled four times in the postseason and they still trusted him to tend their goal more than they did Jack Campbell. Edmonton’s .889 team save percentage this spring just didn’t cut it. McDavid and Leon Draisaitl have three and two years, respectively, remaining on their contracts. It’s imperative to win in this window when they remain in their prime years. So pony up for a Hellebuyck trade. With just a year left on his deal and so much uncertainty in Winnipeg, there has never been a better chance to get him.

STEVEN ELLIS: I’m with Matt here: the Oilers need a goaltending upgrade. Hellebuyck is the one in the rumor mill now and if it’s really over in Winnipeg, Edmonton would be an excellent landing spot. But what about one of Boston’s goalies, like Jeremy Swayman or Linus Ullmark? Brandon Bussi has emerged as a potential backup option, and perhaps the Bruins could look to cash in on one of their two starter-caliber goaltenders this year. The Oilers can’t keep wasting time – McDavid and Draisaitl deserve better. And any of Hellebuyck, Swayman or Ullmark could take No. 1 duties next year.

MIKE MCKENNA: For me it’s a new defensive system. Watching the Oilers chase all around creation in their defensive zone against the Golden Knights was tortuous to watch. And without a complete overhaul to Edmonton’s personnel – at both the defense and forward positions – I don’t see how coach Jay Woodcroft can possibly think the current man-on-man system is going to work against the West’s best. The Oilers were so confused in their defensive zone. Coverage was blown left and right while Edmonton players accidentally double- and triple-teamed the Vegas puck carrier. The Oilers are so talented that they can get away with it against lesser teams. But their defensive structure simply hasn’t been effective in the postseason. Playing man-on-man takes effort, awareness, and brainpower. And I don’t think Edmonton ever had all three ingredients available this season.

NICK ALBERGA: Furthering Mike’s sentiments, I think it’s paramount that Edmonton adds at least one more quality top-four blueliner. Up front, I truly believe they have a good enough roster to get the job done. Additionally, Dylan Holloway’s a player that needs to take a significant step next season in order for the Oilers to have success. While it’s easy to blame the goaltending for the latest postseason exit, I just don’t think Edmonton has nearly enough depth on the back-end, especially when you compare them to some of the league’s elite teams. And don’t get me wrong, grabbing Mattias Ekholm at the trade deadline was huge. They just need more.

The future of the core four

This, by far, is one of the hottest topics heading into the summer. Toronto’s top four forwards – Auston Matthews, Mitch Marner, John Tavares and William Nylander – have been unable to escape the headlines after another disappointing playoff run. They were great in the first round against Tampa Bay, but fell apart when it mattered against the Florida Panthers with the group combining for just two goals along the way.

Tavares and Marner are both signed north of $10 million until 2025, with Tavares boasting a no-movement clause, while Marner’s kicks in next season. Matthews and Nylander both have one more year on their deals, with Nylander ($6.962 million) likely getting the biggest raise. The four players combine for about 42 percent of the team’s salary, which makes things difficult with 10 UFAs and one RFA this summer.

The top priority this summer has to be signing Matthews to a long-term deal. He’s already making $11.64 million, so a new deal won’t be a huge increase. So, really, it’s more about fitting Nylander into the equation if they’re going to end up keeping him past next season that could be difficult before giving Marner an increase the following season.

But does moving any of them really make sense? Can you good enough value for any of them? We’ve seen that the salary cap era makes big hockey moves a huge challenge. Unless they’re getting a deal like Florida got in the Tkachuk/Huberdeau swap, you’re not likely getting fair enough value for a player of their quality.

Goaltending

The Maple Leafs have six goaltenders signed for next season – most notably, Joseph Woll and Matt Murray. Ilya Samsonov, a pending RFA, seems most likely to resume No. 1 duties after a great first season with the club. He was excellent after being a reclamation project from the Washington Capitals, coming over a one-year, inexpensive “prove it” deal that really seemed to pay off for all parties involved.

And then there’s Woll, who was excellent in the AHL and great when called upon by the big club. Woll has another two years signed at $766,667, giving the team some nice cap relief as a backup goaltender. There’s no question about it: he’s ready for full-time duty.

So, the big question: what’s next for Murray? The oft-injured goaltender had his fair share of ups and downs this season and holds the biggest cap hit at $4.687 million. It didn’t take a rocket scientist to know Murray’s acquisition was going to come with some major difficulties, and it reared its ugly head this year. It’s hard to have confidence in a goalie who has missed nearly 70 games since March 2022, and with Woll ready to go, the Leafs need to figure out something here.

UFA’s

Let’s set the stage here: according to CapFriendly, the Leafs have $8,895,217 in projected cap space for 2023-24. That’s with 10 current UFAs and a potential starting goalie to deal with. There will be the full-time graduates within the system, including Matthew Knies and potentially Pontus Holmberg and Bobby McMann. But otherwise, the Leafs will still need to figure out how to clear some cap space to make this all work.

Toronto has easily one of the most interesting UFAs this summer in forward Michael Bunting. At his best, the Scarborough native is a valuable contributor who has proven he can break the 50-point barrier while playing with members of the Core Four. At his worst, he can go on long, difficult stretches of nothing, or get on the wrong side of the NHL’s Department of Player Safety. His value definitely fell after a topsy-turvey season, and keeping him might mean taking a bit of a hometown discount.