Down Goes Brown: Winners and losers from NHL free agency

Maple Leafs GM Kyle Dubas details the process of signing John Tavares, and why he feels the star centreman chose Toronto as his next destination.

Another July 1 has come and gone in the NHL, meaning we’re now a day into the free-agency market. And for once, we had some Canada Day fireworks to enjoy. An actual, honest-to-goodness NHL star in his prime actually made it to the market. Not only that, he changed teams. You probably heard about it.

John Tavares wasn’t the only name on the move. But he’s the one we have to start with, because this is a winners and losers column. And for one of the only times in the last half-decade or so, the big winners in the NHL were the Toronto Maple Leafs. That’s confusing, and a little scary, but here we are. So while we’re all trying to sort through this strange new world we’re living in, let’s start our July 1 rundown in the only place we can.

Winner: The Maple Leafs

They actually pulled it off. They lured a local hero back home, and even got a bit of discount in the process. For all the fun you can have with Leafs fans and their constant belief that every superstar secretly wants to come to Toronto, this time it really happened. As Tavares himself put it, the Leafs won this sweepstakes because they could offer a chance to live a childhood dream.

So now what? This is where the contrarian reflex is supposed to kick in. But at least in the short term, it’s honestly hard to find any kind of downside here for the Leafs. They’ll pay Tavares the league max this year, almost all of it in bonuses, but they have more than enough cash flow and cap room to afford it. Things will get trickier in 2019-20, once the Auston Matthews and Mitchell Marner extensions kick in, but even that crunch could be manageable. (And seeing Tavares leave a little money on the table could encourage the younger players to do the same.)

For now, the Leafs are as strong down the middle as pretty much anyone, and the idea of either Tavares or Matthews getting easy matchups is scary. The blue line still needs work Frederik Andersen isn’t a sure thing, and the Leafs still have to get through Tampa and Boston to get out of the Atlantic, so there’s work left to do. But even for a lifelong Maple Leafs cynic, there’s really no way to spin this: It’s a huge win for Toronto.

Loser: New York Islanders fans

Honestly, we don’t even have a joke here. This is a brutal, brutal moment for Islanders fans.

For some teams, watching your franchise player walk away for nothing would be a wakeup call. Not for Islanders fans. They’re already wide awake. They’ve had plenty of time to worry that the team was adrift; that Charles Wang and Garth Snow and the arena mess and one playoff series win in 25 years had dug a hole so deep that even new ownership and Lou Lamoriello and Barry Trotz couldn’t dig out of it. They’ve had years to think the worst. They’re used to it.

But it’s one thing to think the worst. It’s another to have a once-in-a-generation player look you dead in the eye and tell you that you’re right. Tavares can soften this with talk of childhood dreams and coming home, and there’s no doubt something to that. But the brutal truth remains: In a league where star players always choose to stay put, the Islanders were the one team who couldn’t convince theirs to stay.

That stings. And it has some Islanders supporters lashing out, with the predictable stream of YouTube clips of outraged fans and burning jerseys. But once the initial bitterness clears, the question will be where this team goes next. It’s upgraded the front office and behind the bench, even if it turned out not to be enough for Tavares. A goalie is needed, and now a top-line forward. There’s plenty of cap space, which is good news if it’s used wisely and bad news if there’s a knee-jerk panic move. So far, the early indications aren’t good.

That’s… I mean… yikes.

Whichever way the Islanders go next, there are going to be a lot of tough questions for a team that chose not to trade Tavares for a windfall at the deadline. Eventually, there will be answers, and in the long term some of them may even be positive ones. Just not right now. Right now, it’s nothing but brutal.

Winner: Kyle Dubas

The Leafs roster is the big winner, but let’s not forget about their new GM. Kyle Dubas’s first major moment in the Toronto spotlight saw him face down his old mentor, and walk away with Lamoriello’s franchise player. That’s not a bad start, and it will no doubt buy Dubas some goodwill with the Toronto market. At this rate, nobody’s going to call for him to be fired until next week at the earliest.

Winner: The Tavares suspense

As painful as it may have been at times, the Tavares roller-coaster delivered. A few weeks ago, it seemed like he may re-sign with the Islanders before the sweepstakes ever got off the ground. Even a week ago, it still felt like we were headed to a Steven Stamkos-style anticlimactic ending. At the very least, we all assumed that we’d know something before July 1.

Instead, Tavares didn’t just make it to the open market – he did it with some genuine mystery around where he’d wind up. It all made for a fun ride, and probably the most interesting off-season day since those infamous 23 minutes back in 2016.

Other leagues get to do this every year. In the NHL, it’s a rarity. Here’s hoping that changes, and that Tavares might inspire a few fellow stars to test the waters.

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Loser: The non-Tavares suspense

Oh right, everyone who wasn’t John Tavares. Almost forgot about those guys.

By Sunday morning, Tavares was just about the only big-name left whose destination hadn’t leaked. John Carlson, Evander Kane and Mike Green didn’t even make it to Monday. Rick Nash removed himself from the running, at least temporarily. We knew where Ilya Kovalchuk, Paul Stastny, James van Riemsdyk, Jack Johnson and even Ryan Reaves would wind up before the markets officially opened.

That’s the downside of the league’s multi-day window for negotiating with pending UFAs. It removes some of the pressure on teams to make crazy offers on July 1, which probably helps GMs make slightly smaller mistakes than they typically would. But much like the trade deadline has done over the last decade, we’re seeing UFA day morph into a week-long process that doesn’t always leave a lot of drama as the clock ticks down. Tavares provided some, but once he was off the board it was slim pickings.

Winner: The Philadelphia Flyers

They landed van Riemsdyk on a five-year, $35-million deal. That cap hit is a bit higher than most seemed to be expecting, but only a bit. And the five-year term is a year or two less than what the rumour mill had suggested.

Eating a little bit more salary to keep the term manageable on star players is a smart strategy that more teams should be willing to employ. In this case, it landed the Flyers a consistent goal scorer without committing to a big chunk of his mid-30s.

Loser: The Vancouver Canucks

July 1 is generally a disaster for NHL GMs, who repeatedly make the same mistakes year after year. But if there’s one lesson that should be all but impossible to ignore, it’s this: Don’t give term to depth.

Depth is important. You can’t win without it. But it also doesn’t tend to be all that hard to find. And it’s not something you typically should need to commit multiple years to lock down.

Apparently, Jim Benning doesn’t see it that way. He signed 32-year-old Jay Beagle and 28-year-old Antoine Roussel to matching four-year deals that will carry $3-million cap hits. Why go that long for players who figure to slot in on the third or fourth line? As Benning explained it:

That’s probably true. But sometimes the market is wrong, or at least unreasonable. Smart teams walk away from the market when the numbers get silly.

Both Roussel and Beagle will fit in fine in Vancouver, and should contribute at least a little to a team working to turn things around. But in another year or two, when the Canucks may be ready to get back to contending for a playoff spot, those deals are unlikely to look very good. Kicking the salary cap can down the road can sometimes makes sense, but not when “down the road” is where you’re expecting to competitive again.

Winner: The Vegas Golden Knights

For the second time, Stastny went into the UFA market and was willing to come away with a shorter term. Apparently, it’s kind of his thing.

That works for the Knights, who may well have walked away from yesterday with the single best value deal of the day. And they’ve still got plenty of cap space left to do something big – maybe on the trade market, where Erik Karlsson still looms. More on that in a bit.

The Knights’ other big signing was Reaves, who comes back on a deal that carries a $2.775-million cap hit. That’s pricey for what he brings to the table, and will almost certainly be a deal that Vegas regrets. But again, the term was reasonable. Reaves got two years, so even if he’s a bust the Knights can buy him out or trade him without too much trouble. Slowly but surely, NHL teams are figuring out how to manage term, and the Knights seem to be one of the faster learners.

Winner: Drew Doughty

This wasn’t a July 1 signing, but it was the biggest contract of the weekend so it warrants a mention. As expected, Doughty hammered out an extension with the Kings that will keep him in L.A. through 2027. And he got it done without an agent, which will put a few extra dollars back into his pocket.

Is it a good deal for the Kings? That’s a tougher question. In the short term, sure – as the Islanders just demonstrated, letting a key player head into the final year of his contract can be a recipe for disaster. But as for the future, well…

The contract will also make Doughty the highest paid defenceman in the NHL, soaring well past P.K. Subban‘s $9-million hit. Well, at least until Karlsson signs. Speaking of which…

Loser: The Ottawa Senators stay quiet

The Senators didn’t do anything of any significance yesterday, which was to be suspected – this isn’t a team with a ton of money to spend. Still, with plenty of key players to either sign or extend, you could forgive Sens fans if they were hoping against hope for some good news. If not a Karlsson extension, maybe Mark Stone or Matt Duchene. Instead, nothing.

That wasn’t a surprise. But the pressure is on the Senators now. They’ve spent the off-season telling their fans that they’d wait until July 1 to make their case to Karlsson, even as guys like Doughty, Ryan McDonagh and Oliver Ekman-Larsson were agreeing to new deals in advance. If you’re an Ottawa fan, you could at least convince yourself that things were on track. But now July 1 has come and gone, and there’s no more using the calendar as an excuse. Karlsson can sign whenever he wants. Now we find out if he wants to.

For what it’s worth, the Senators say they made their offer yesterday. Maybe they offered enough to get a deal done, or at least to generate a conversation that leads to one. Or maybe it was just the team’s latest attempt at PR spin to a fan base getting tired of it.

A trade out of Ottawa still seems like the most likely scenario, and if there’s good news here for the Sens, it’s that the rest of the blue line class of 2019 signing extensions means Karlsson is head and shoulders above anyone else who could be on the market. In theory, that means the Senators can pump up the asking price, and insist that trade suitors be ready to pay big. Of course, it could also mean that they decide to focus on unloading Bobby Ryan‘s contract instead. Time will tell. But as of yesterday, the time is now.

Loser, but only temporarily: The San Jose Sharks

They lost out on Tavares despite a strong pitch. That’s disappointing, but it leaves GM Doug Wilson with plenty of cap room to work with, even with Logan Couture‘s extension done. That makes the Sharks one of the most fascinating teams to watch over the coming days.

At a high level, the Sharks roster looks a lot like the Kings’ – they’re good, they’re locked up long term, and they’re not quite old but they’re getting there. There aren’t many big names left, so Wilson may have to get creative and turn to the trade market. But one way or another, you’d figure he has to do something, and probably something big.

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Finally, let’s close with a few quick hits.

Winner: The St. Louis Blues The bad news is that they paid Tyler Bozak second-line money. The good news is that he won’t need to be a second-line player for them, thanks to last night’s acquisition of Ryan O’Reilly. The former Sabre didn’t come cheap, but he’s the best asset in the deal by far, and the cap hit balances out fairly well for them.

Loser: The Winnipeg Jets They were a darn good team before Stastny arrived, and they’ll be a good one with him gone. But seeing a top UFA walk away will reinforce the old idea that the Jets are at a disadvantage when it comes to attracting top players. Finding a way to dump Steve Mason‘s contract freed up some space, which is good. But can they find somebody to spend it on?

Winner: The Edmonton Oilers Peter Chiarelli didn’t have much room to work with, and given some of his recent UFA work, maybe that was a good thing. But picking up Kyle Brodziak and Tobias Rieder on cheap-ish deals was a decent day’s work.

Loser: The Detroit Red Wings‘ rebuild – They signed Green, Thomas Vanek and Jonathan Bernier, which doesn’t exactly sound like a youth movement. You can see where Ken Holland is coming from; there’s a playoff spot to be had in the Atlantic, and it’s not like the prospect pipeline is sending a ton of young talent to clog up the lineup. Still, Detroit fans hoping for some long-term vision came away disappointed.

Winner: The Buffalo Sabres Carter Hutton is a gamble, because he’s a goaltender and all goaltenders are gambles. Maybe he’s the next Cam Talbot or Martin Jones; maybe he’s the next Scott Darling. But at $2.75 million for three years, he seems like a decent risk for a team that could use some stability in goal. As for O’Reilly, they got a decent return for a player they probably felt like they had to move – and apparently did it before his bonus kicked in.

Winner: The Montreal Canadiens In the big picture, they lost; they desperately need a top-line centre like Tavares, didn’t get so much as an invitation to even make their case to him, and then watched him land with a division rival. But as far as the weekend goes, they made a smart move to use some cap space to pry Joel Armia out of Winnipeg. That’s not the same as spending money on Tavares or Stastny or O’Reilly, but it’s something, so we’ll be nice and call it a minor win.

Loser: The Jack Johnson signing – Nobody seems to be happy on this one. The Pittsburgh Penguins were widely seen to have overpaid, especially on term, and had to unload a pair of decent assets to make room. Meanwhile, the John Tortorella and the Columbus Blue Jackets are upset over some of the comments made in the fallout.

Loser: The Calgary Flames I’m iffy on this one, so you could probably talk me into a slight nudge into the “winners” column. The Derek Ryan and Austin Czarnik signings were fine. But this morning’s news of a five-year James Neal deal seems like the sort of thing the team will regret. There’s a case to be made that the Flames basically paid a little less money for a little worse version of van Riemsdyk, which is a deal I liked. But Neal is two years older, which shifts the risk equation on those five years. They got their man, and they didn’t do anything crazy to do it, but this still feels like a contract they’ll be thinking of unloading by the midway mark.

Winner: Homecomings – Never let it be said that NHL players and teams don’t appreciate the familiar. Tavares heads home to the team he rooted for as a kid, but plenty of other players are rejoining teams they’ve already played for. That group include van Riemsdyk in Philadelphia, Tomas Plekanec in Montreal, David Perron in St. Louis, Vanek in Detroit, Matt Cullen in Pittsburgh and even Roussel in Vancouver, where he’d had a training camp tryout back in 2011 that everyone had forgot about.

Loser: The trade market – No Karlsson deal, yet. No Max Pacioretty deal, yet. Nothing on Jeff Skinner or Phil Kessel or Milan Lucic. Just the O’Reilly trade on July 1, in fact, and only two minor deals in the immediate lead-up.

All of which is to say: Settle in, because this off-season isn’t done yet.

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