By Daniel Friedman

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It’s an important week for the New York Islanders. The NHL Entry Draft is on Friday and teams can begin communicating with impending free agents on Wednesday.

The Isles are at a crossroads and have a lot of questions to answer. I figured I’d sit down with Pro Hockey Talk’s James O’Brien and ask him a few of those questions. Here’s how the conversation went down:

The Islanders made a big move by going out and getting Jaroslav Halak. What did you think of the move, and what effect do you think it might have on the Islanders’ outlook for next season?

O’Brien: “Love it. After making what seemed like at-best a lateral move by re-signing Evgeni Nabokov last summer, the Islanders actually decided to roll the dice in aggressively pursuing and signing Jaroslav Halak. And by rolling the dice I mean taking less of a risk, as he’s been a dependably useful goalie who didn’t cost them an arm and a leg. At 29, Halak is still at or near his prime. His career save percentage is sterling (.918) and he was even better in his season split between Washington and St. Louis (.921 in 52 games). The Islanders’ team average of a .910 save percentage was the third-worst in the league, so they had plenty of room to improve … and did. That being said, Halak doesn’t have a great track record of staying healthy. If any GM should appreciate the value of a backup, it’s a former journeyman like Garth Snow. The Islanders need to think long and hard about whether or not they’d trust someone in their system to carry the ball for a decent amount of time, as that’s a distinct possibility with Halak. In the grand scheme of things, it’s a great move in the right direction. Goalies are odd beasts, though, so you never know.”

The Islanders made a lot of noise a year ago by taking Pittsburgh to six games, then followed that up with a dud. Which do you think was the fluke — the playoff year or this past season?

O’Brien: “When PHT asked which 2013 playoff team I expected to miss the 2014 postseason, I tabbed the Islanders, so I guess I’d pick the playoff year. Really, the truth is somewhere in between, though. I think that the Islanders should have bulked up quite a bit more for 2013-14, as they didn’t exactly make the playoffs that comfortably. Luck didn’t bounce their way a whole lot this time around, yet you don’t see good teams essentially blaming their misfortunes one or two injuries, even if it’s to a star. The Penguins seem to lose one or more of Sidney Crosby, Evgeni Malkin and Kris Letang for extended chunks of every season and yet they keep making the playoffs. I imagine the natural response will be ‘The Islanders are clearly not the Penguins,’ but eventually that can’t be OK anymore. If you’re not aiming to be a power in your league/division/conference, then what’s the point?”

If you’re Garth Snow, are you drafting at No. 5 or trading the pick? If you’re drafting, who are you looking to pick and if you’re trading it, who are some possible targets?

O’Brien: “How much longer can the Isles be satisfied with landing lottery picks? It’s really all about what’s out there, though; the New Jersey Devils turned the No. 9 pick into an affordable, quality starting goalie in Cory Schneider last summer. In my mind, the Islanders need just about everything — more scoring depth, more defensive options — so combining the No. 5 pick with another asset or two could provide some nice rewards.”

What is this team missing in order to get back into the playoffs, and are there any particular free agents you think could sign with the Islanders and fill those holes?

O’Brien: “As I touched on earlier, the Islanders could use a little bit of everything. Oddly enough, a Matt Moulson reunion tour makes sense to me, but I’m not in the organization that seemed to sour on him. With that likely out of the question, players like Radim Vrbata, Mikhail Grabovski and Steve Downie — maybe even two of them — could help tilt the ice in the right direction. A cheap deal for Dustin Penner seems sensible as well, especially if you let him clean up Tavares and Okposo’s garbage. One player I’d recommend for just about any defense-lacking team is Ron Hainsey. He enjoyed nice possession stats last season and comes with a possible ‘blackballed by his union involvement’ discount, though that likely wears off compared to 2013. Tom Gilbert is another guy who could be cheap and competent, a combination the Isles badly need on D. Snow has a knack for finding bargains, so why not add a few this summer?”

Jack Capuano has received mixed reviews. What’s your take on the Isles’ head coach, and do you think he should’ve been fired? How much longer do you give him in NY?

O’Brien: “People who follow the Islanders on a day-to-day basis can probably answer this question with deeper analysis about the way he deploys his players and how many different ties he owns. As an outsider, my impression is simply that he’s just a ‘guy.’ It’s not totally fair, especially since he hasn’t been outfitted with star-studded rosters. Still, there are some chefs who can make quite the feast out of limited ingredients, but Capuano doesn’t strike me as a guy who really moves the needle. The move to Brooklyn makes the 2014-15 season do-or-die for him, if he even makes it through the whole thing. I’m guessing Snow has more to do with that than Capuano.”

Garth Snow’s had some ups and downs over his tenure. What’s your overall impression of him?

O’Brien: “I cannot help but make parallels between Garth Snow and Joe Nieuwendyk, even if one enjoyed a slightly more impressive career on the ice. To be more specific, each GM seemed to excel in an area or two while having enough flaws to make them endangered executives. Snow impresses with his ability to spot valuable players at bargain prices. For all the credit the new Dallas Stars regime receives, Nieuwendyk left behind an immaculate salary structure that only looks better with Tyler Seguin in the mix. Unfortunately, Snow doesn’t enjoy the highest batting average when it comes to blockbuster moves. The Moulson trade didn’t work out. The Nabokov gamble was a big bust. Many blame Charles Wang for the Rick DiPietro contract, but it’s remains the elephant in the room. He’s made bold moves only to see potential new players balk either initially (Evgeni Nabokov, Lubomir Visnovsky) or altogether (most recently Dan Boyle). I don’t mind the practice of sending picks for negotiating sneak previews especially considering the circumstances, yet it backfires with unsettling frequency. He also tried to give up an entire draft to move up from Griffin Reinhart to Ryan Murray and was denied. I know that was considered a weak year for prospects but good grief that’s just a mind-blowing scenario. Maybe I should stop here because Snow holds some really weird grudges. I think he’s sneaky good at times, yet he needs a great offseason and 2014-15 run to make it to Brooklyn.”

Are there any prospects or players within the Islanders’ organization that you would deem expendable? Who and why?

O’Brien: “At this point, the Islanders should be open-minded to moving anyone except absolute prime prospects and key roster players like Halak, Tavares, Okposo, Nielsen and Travis Hamonic. At some point, you need to make leaps instead of baby steps toward being a contender. That fork in the road is approaching soon.”

What’s your opinion of Josh Bailey? Do you think he’ll ever pan out?

O’Brien: “Josh Bailey’s possession stats were pretty impressive this season, which keeps me from burying him outright. That said, can we get this kid to shoot the stinking puck? He only generated 566 shots on goal in 406 career regular season games, including just 98 SOG in 77 games in 2013-14. You’d need Joe Thorntonian passing skills to be an offensive asset while being so gun shy. Honestly, I wouldn’t be surprised if he ends up like Benoit Pouliot: a punchline because of his high-first-rounder status yet eventually a useful player. The question is: will Bailey need to leave the Islanders to shake those ‘bust’ worries and just reach whatever potential he has? Sometimes it’s hard for a guy labelled a ‘reach’ to just get on with his career without receiving a change of venue.”

The Islanders are moving into a new arena in 2015. What kind of effect do you think this will have on the organization?

O’Brien: “I think it will be enormous. Going from what’s described as one of the worst arenas in professional sports in Long Island to a flashy building in hipster-tastic Brooklyn is a quantum leap in drawing power. Andrew Ference is probably already calling Taylor Hall a donkey and Ryan Nugent-Hopkins a pixie in hopes of getting traded to the Islanders. All weird jokes aside, the Islanders could very well end up in a better venue, in a hipper area and bask in a beefier budget by moving to Brooklyn. Let’s just hope they keep those throwback sweaters in some form, though.”

Can you see John Tavares requesting a trade anytime soon?

O’Brien: “No, and even if he wanted one, the Islanders would be insane to listen. He’s an $8 million guy making $5.5 million through the 2017-18 campaign. At 23, he’s entering that glorious peak period where a player combines still-elite athleticism with the experience of knowing the lay of the land. It’s imperative that the Islanders transfer the money they’re saving on the likes of Tavares and Okposo to players who can make certain that good things are happening even when those two are huffing and puffing on the bench.”

James O’Brien writes for Pro Hockey Talk. You can follow him on Twitter @cyclelikesedins.

Follow Daniel Friedman on Twitter @DFriedmanOnNYI

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