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The Wraparound: If It's About Winning, This Decision Shouldn't Be Hard

By Ty Anderson, 985TheSportsHub.com

(Welcome to 98.5 The Sports Hub's The Weekend Wraparound -- or just The Wraparound, WW, Wrap, or whatever you care to call it. I'm not big on names. But here's what you should know about it: It's a new weekly column that will run every Saturday in addition to our complete coverage of the Boston Bruins, with or without ice available.)

We're less than 24 hours away from the start of NHL free agency and we're not any closer to a decision from John Tavares.

And apparently all six teams that the 27-year-old superstar met with -- the Boston Bruins, Dallas Stars, New York Islanders, San Jose Sharks, Tampa Bay Lightning, and Toronto MapleLeafs -- are still in the hunt. You can understand why it's taken Tavares some time to make his decision, too. From potentially spurning the team that drafted him No. 1 overall in 2009 to figuring out where he's going to live, if the team he chooses has the long-term stability he's lacked during his time with the Islanders, and if the allure of his hometown is enough to sign on the dotted line in Toronto, there's a lot to consider.

But if this decision is about winning, it's an easy one: It's the Bruins. Every. Single Time.

With all due respect to the other teams involved, I'm not sure any of them can really match what the Bruins have right now.

The fact that we've come this far and Tavares has not re-upped with the Islanders -- and this is just a feeling, mind you -- feels like that's bad news for the Isles. Of course, that can change before midnight. But if it does not, you have to feel as if they would be out of the running. Rightfully so, as the organizational dysfunction around that team has failed to put much of anything around their superstar talent. They have some promising now in town or on the way shortly, but how many more years of his prime can they honestly expect Tavares to throw away as they try to build a contender in New York?

If we are to consider the Maple Leafs the next favorite, that's great, but have we read into their numbers issues? Or the fact that the Maple Leafs have yet to re-sign any of the youthful pieces of the core that will make them a legitimate Stanley Cup threat. William Nylander is this year's piece to be re-signed. Now, if the Leafs are smart and ink Nylander to a long-term deal, you're probably talking about anywhere from $6.5 million to over $7 million per season. Next summer, meanwhile, needs to come with new contracts for Auston Matthews and Mitch Marner. That should run the Leafs at least $20 million combined. You're up to $27 million for three players now, and then you're adding Tavares in at say $11 million per season. That's $38 million of 2019-20 cap devoted to four players, leaving the Maple Leafs with around $2 million in projected space. The Leafs also remain on the hunt for a No. 1 defenseman, which never comes in at less than $8 million in today's league.

In other words, Tavares would be signing on for a ridiculously top-heavy grouping that makes the Leafs more Chicago Blackhawks Jr. than anything else. The biggest difference there is that the Blackhawks have actually, y'know, won a Cup. The Leafs would be paying Cup-winning premiums on a core that still may not be enough to end Toronto's drought.

The Lightning are an interesting one, and would essentially confirm Tavares' status as hockey's Kevin Durant. But it would also have to come with serious cap-maneuvering on the part of the Lightning. That's easier said than done for the Bolts, too, considering the masterful job done by Steve Yzerman, as the Lightning do not have many contracts you look at and go, "Oh, that's the one that has to go." In essence, the Bolts would have to move multiple contracts off their books, and deal significant blows to their middle-six in the process. Oh, and they have to re-sign Nikita Kucherov next year. It's a Danny Ainge summer.

The Stars? Cool. Have fun going to the Stars. That's basically become Hockey Siberia. You could put up gaudy numbers galore, but you'd basically be hockey's version of Mike Trout with the Los Angeles Angels of Anaheim of California on Planet Earth. Nobody would notice a thing you did, you probably wouldn't win anything, but we'd all be subjected to hype every year. (If I sound bitter towards the Stars, I swear it's only because I've been suckered into this hype more times than I can count.)

San Jose, meanwhile, is probably the closest comparable to the Bruins in terms of what they can offer right now with cash and an immediate chance to win. The Sharks are not loaded with long-term commitments up front -- Evander Kane is making $7 million per for the next seven years and Logan Couture is about to sign an eight-year extension worth $8 million per season -- and their total commitments for the 2019-20 season is currently $36 million below the salary cap (though that's without new deals for restricted free agents Tomas Hertl and Chris Tierney). Adding Tavares to that seems like it would be easy enough.

But what happens after that? Is team captain Joe Pavelski (a free agent next summer) retained and how much does that run you? What about Martin Jones? Can he truly be the guy to lead you back to the Stanley Cup Final after failing in his two postseason runs since? And do the Sharks have the prospects to step up and into the mix when heavy contracts begin to weigh the team down? Ask around and it's hard to get a considerably glowing review of the Sharks' organizational pipeline.

Would Bruins general manager Don Sweeney bring this up in his talks with No. 91? Probably not. It's probably considered dirty pool, and playing the 'This Is Why We're Better, So Please Like Us' card may do more harm than good.

But just boil it down this way: If the Bruins have Tavares on their roster this past postseason, they are in the third round of the Stanley Cup Playoffs, at the very least. And if this is not about the long game -- which, at 27, it really shouldn't be -- it's in Boston that Tavares has the best opportunity for short- and long-term gains as a legitimate Stanley Cup threat.

Brad Marchand and David Pastrnak are in the prime of their careers and signed for less than $7 million per season. In fact, the entire Boston top line (adding Patrice Bergeron to that group) costs less than $20 million in total. Speaking to their strengths up front, the Bruins can legitimately look at Tavares and say, "OK, who do you want as your go-to winger: Pastrnak, Jake DeBrusk, Anders Bjork, Danton Heinen, or Ryan Donato?" There's more high-impact wingers on their way to Boston, too. Moving beyond their forward depth, the Bruins have a No. 1 defenseman of the future in Charlie McAvoy and the 41-year-old Zdeno Chara is still chugging along as a legitimate top-pairing shutdown presence. And I don't care how you feel about Tuukka Rask, but if Tavares comes to Boston, Rask immediately becomes the best goaltender he's ever played with.

And the pieces the Bruins would have to trade in order to add Tavares to the fold -- probably David Backes and/or David Krejci, though the Bruins could probably have one year of a Bergeron-Tavares-Krejci combo -- are players that Sweeney is likely going to have part with at some point in the foreseeable future anyways given their age/contract status.

Quick, Sweeney, get me on the line.

Loose pucks: It does indeed sound like Anton Khudobin will be leaving the Bruins (again) this summer. According to Khudobin, the Bruins and his camp were about $150,000 off in their negotiations. In an attempt to find some middle ground, Khudobin claims he tried getting them to add another $50,000, but that the Bruins said no. I would watch the Islanders and Stars as potential landing spots for Khudobin... My favorite Anton Khudobin story I've never found a way to work into a feature: Khudobin once explained to me in great detail how he tried to be an extra coach when on the bench. He was really proud of the way he helped Brandon Carlo grow in his first year in the National Hockey League. I asked Carlo about it. "I never knew what he saying," Carlo said... Rick Nash is indeed considering retirement. Likely due to his concussion problems, Nash's decision to forego the July 1 signing period will see him leave at least $15 million on the table, as he had no shortage of suitors (including the B's). Sweeney said he 'respects the hell' out of Nash's decision no matter what he decides. If the Bruins still have cap space and an opening come August, the 34-year-old Nash could be a good fit... No matter what happens with Tavares, the Bruins need are a middle-six winger, preferably on the right side, left-side defensive depth, and a backup goalie.

Ty Anderson is a digital producer for 985TheSportsHub.com. Any opinions expressed do not necessarily reflect those of 98.5 The Sports Hub, Beasley Media Group, or any subsidiaries. Have a news tip, question, or comment for Ty? Follow him on Twitter @_TyAnderson.