NHL free agency begins on July 1, so to get you fully prepared, we offer our insights on all the big questions leading up to the frenzy:

Greg Wyshynski, senior writer: My heart still says he remains with the New York Islanders, because I’m a sucker for all of his declarations of wanting to bring glory back to that organization. And, well, because I always believe a player will want to stay with their stuff, and his stuff is on the Island. But my head tells me that he spent two days getting overwhelmed by pitches from teams a heck of a lot closer to winning a Stanley Cup, from San Jose to Boston to Toronto, his hometown team. So my heart says the Islanders. My head says the Sharks.

Emily Kaplan, national reporter: All season, I believed Tavares would opt for loyalty and the Islanders. Over the past few days, my gut tells me the San Jose Sharks. GM Doug Wilson — forever chasing the biggest names — finally gets his man. If Tavares really wants to win a championship, the two suitors best-equipped to win now are the Lightning and Sharks. Only one of those teams has the cap space to make it work on the spot.

Chris Peters, hockey prospects analyst: As much as I think his getting to hear pitches from numerous teams to see if the grass is greener, I haven’t budged from my position that he’s likely to return to the Islanders. New management, new coach, new ideas, a new arena on the horizon and a new path forward all strike me as things Tavares wants to be a part of. Now they just need to find a new goalie.

Ben Arledge, Insider NHL editor: I’m not sure Barry Trotz would have signed on with the Islanders if there wasn’t an overwhelming chance that Tavares was staying put. Tack on an outstanding draft in which the Islanders added a potential future winger for JT in Oliver Wahlstrom, and the case for going nowhere gets stronger. There’s plenty of talent there, none better than Mathew Barzal, and if the Islanders figure out the goaltending situation — and defense, to a lesser degree — then I think it’s the final landing spot come July 1. If he does decide to venture off the island, look for Tampa Bay (no state income tax, and his buddy Steven Stamkos) or Toronto (the 1-2 punch of Auston Matthews and Tavares isn’t too shabby) to be in focus. After all, the Lightning do offer him, without a doubt, the best opportunity to hoist the Cup.


Which team is going to “win” free agency?

Wyshynski: The real answer is “the team that dabbles the least in unrestricted free agency because not good can come from it,” but I’ll go ahead and predict that Ray Shero and the New Jersey Devils do well for themselves. They have over $24 million in cap space and only nine forwards under contract, so one assumes they’ll dabble for players like James van Riemsdyk and potentially re-sign deadline pickup Patrick Maroon. Of course, trades are always a possibility, and after Shero’s masterstroke waiting out the Capitals’ cap crisis to snag Marcus Johansson, expect more of the same.

Kaplan: Honestly, I believe the defending champion Washington Capitals already won it. Think about it: the point of free agency is to augment your team by taking calculated risks without overspending, while opting for known commodities when possible. The Capitals found a way to make it work with the No. 1 defenseman on the market, John Carlson. They are also welcoming two of their ascending playoff performers back — Devante Smith-Pelly and Michal Kempny — while fending off suitors who were willing to offer more in money and term. Washington returns essentially the same exact roster next season; in the salary cap era, this is something that has proved incredibly difficult for Cup winners (see: Pittsburgh Penguins, Chicago Blackhawks).

Peters: I feel like the trade market is going to be more lucrative than free agency and the place where teams can make the biggest impact on their roster, but I’m going to go with the Winnipeg Jets. They have to take care of their own house a bit first with key restricted free agents like Jacob Trouba, Josh Morrissey and Connor Hellebuyck to get signed, but if they could find a way to keep Paul Stastny and maybe add some smaller pieces around what they already have, they’re going to inch that much closer to Stanley Cup contention. The Jets are close enough to taste it now and I think ownership should be ready to go for it without overextending themselves.

Arledge: Well, the answer to this one is no different from the previous one — the team that lands Tavares wins, period. That said, the Boston Bruins are also in a good position. Even if they miss on Tavares, van Riemsdyk would offer them a power winger to fill the Rick Nash role in front of the net and solidify a second scoring line. He potted 36 goals last season, and would do well on a line with David Krejci and Jake DeBrusk. Maybe it’s Michael Grabner who the B’s add. Nail Yakupov is an interesting option, too. They have some cap space to toy with to further shore up the offense, and they don’t even need to make a splash to do it.


What should the Islanders do in goal?

Wyshynski: It’s been indicated that the Islanders don’t have much interest in Robin Lehner, which is confusing because he’s arguably the best goalie available on the UFA market. If I were Lou Lamoriello? I’d sign Jonathan Bernier, who had a career reawakening with the Avalanche, to a one-year deal. I’d hope that Thomas Greiss can figure himself out. And then a pray that either Ilya Sorokin or Linus Soderstrom is ready to make the jump in the next two seasons.

Kaplan: First, I’d hesitate to give any of the goalies on the market a more than a two-year deal. The available crop is damaged goods, and the Islanders have been saddled by too many bad goaltending contracts to be fooled again. That said, I’d look to a known commodity: Craig Anderson. The 37-year-old still has plenty of good hockey in him and the Senators are shopping him. Anderson is under contract for two more seasons — a perfect bridge deal for the Islanders’ transition — and hey, his $4.75 million cap hit is certainly manageable, especially if the team finds itself with extra cap space if a certain center decides to sign elsewhere.

Peters: I don’t think there are a ton of great options available to the Isles right now. Even though they have talented Russian goalie Ilya Sorokin in the system, I’d consider taking a run at a younger goalie via the trade market. What would it take to get Jon Gillies out of Calgary? It sounds like the Toronto Maple Leafs would be willing to listen to offers for recently crowned AHL champion Garret Sparks. It’s hard to say if either of those guys are bona fide starters right now, but they intrigue me more than anything on the free agent market.

Arledge: Lehner is the most intriguing option for me — if and only if Capitals goalie coach Mitch Korn does follow Trotz to the Islanders as has been rumored. There’s no question Lehner has talent, but he needs the right coach and team to reach his potential. Korn could certainly be the guy to get him there. The Islanders just need a filler as they wait for Sorokin and Soderstrom to come into the fold, so why not take a shot with the big Swede?


Suggest one player-team perfect fit:

Wyshynski: While they might not want to hand out the term he’s looking for, I’d love to see “The Real Deal” James Neal reunited with the team that tossed him into the expansion draft pool, the Nashville Predators. They could use a 20- to 25-goal scorer on right wing, with a little playoff truculence. Plus, it’d be nice to see both player and team finish what they started.

Kaplan: Paul Stastny, Winnipeg Jets. How will GM Kevin Cheveldayoff get it done? To that question, I have no answer. It will take serious finagling — especially with the Jets’ eight RFAs to re-sign, including goalie Connor Hellebuyck, as well as a potential extension for Patrik Laine. So maybe Cheveldayoff has to move someone like Jacob Trouba. It’s worth it, considering the glimpse we saw of Stastny last season as an ideal complement to Laine on the second line. Oh and six goals and nine assists in 17 playoff games. Enough said.

Peters: I don’t think this is going to happen, but I’m going to go there anyway. John Tavares is the good ol’ Ontario boy the Maple Leafs have craved. He’d provide an unrivaled 1-2 punch with Auston Matthews, he’d have high-end wings like Mitch Marner or William Nylander (or both) to flank him, and he’d probably be able to pull down every Toronto-area endorsement under the sun. The Maple Leafs would vault to instant contender status, with just a little more help on defense needed.

Arledge: Greg alluded to it earlier, but van Riemsdyk to the Devils just makes sense. An emerging contender with plenty of youth and the reigning MVP, New Jersey was still just 15th in the league in scoring last season. Add in JVR and his 36 goals to the top six and the No. 1 power-play unit, and you suddenly have another serious scoring threat alongside Taylor Hall. And the Devils have the cap space. Making the plunge on the 29-year-old Garden State native would give them a front-of-net presence and a dominant man-advantage group.


On which player would you issue a “buyer beware” warning?

Wyshynski: David Perron didn’t just have a career year in 2017-18 with the Vegas Golden Knights, he obliterated his previous career high in points per game (0.73) with a 0.94 average, scoring 66 points in 70 games. But among the things that might be unrepeatable about the Golden Knights next season, 66 points from David Perron is one of them. Whether he stays in the desert or moves on to greener pastures, I anticipate a re-calibration back down to around 40 points.

Kaplan: There seems to be so much love for Carter Hutton on the open market. In fact, he’s the likeliest free agent goalie to get at least a three-year deal. Indeed, Hutton is coming off a terrific season — pushing Jake Allen in St. Louis and posting a .931 save percentage through 32 games — but let’s be honest about expectations here. Hutton is 32. He’s a career backup who cycled through three organizations in the past six years. He might be a fine starter next season, but don’t expect him to suddenly blossom into Braden Holtby.

Peters: The defense market would scare me quite a bit as a GM. Losing John Carlson from the free agent pool was good news for everyone else on that UFA list. Mike Green seems like a guy that’s ripe for overpayment. As much as I think the 32-year-old can still play, I’d be concerned that the weak market raises his dollar value to a point where it just doesn’t help. He’s still a solid option at the right amount, but I’d have a hard time committing multiple years and anything close to the $6 million average annual value he made on his last contract.

Arledge: I wouldn’t attach myself to any of the free agent goaltenders for more than a season or two. There are a lot of young wild cards and aging veterans on the decline in the group, and no one screams out anything other than a temporary stop-gap to me. I’d also caution against giving big money to Brooks Orpik. A team might be enamored by his strong postseason with the Capitals, but at the end of the day, we’re talking about a defenseman who will be 38 when the season starts, has never offered much offensively and has certainly lost a step or two.

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