Winners and losers of Day 1 of NHL Free Agency

Day 1 of free agency is in the books! Which means, depending on who you happen to cheer for, you either woke up this morning uproariously happy or outrageously mad. 

Regardless, a lot went down on Friday. And despite the odd timing and technical challenges brought forth by these uncertain times, free agency nonetheless produced its usual certainties, leaving some teams as winners and some teams, well, losers. 

So in the spirit of this, the Halloween season, let’s figure out which of yesterday’s participants ended up getting tricked, and which went home with a treat. 

Loser: Vancouver Canucks

Before Andy Reid won a Super Bowl last season, the single flaw which held him back from coaching greatness was his struggle with clock management. So bad was this achilles heel of Reid’s that Chiefs fans soon developed a running joke that, if the team would only hire someone solely to stand next to Reid and tell him how much time was left in the game, their loveable walrus would be unbeatable. 

Jim Benning is no Andy Reid, of course — Andy Reid is actually very good at his job — but the Canucks GM desperately needs his own specialty coach. Namely, someone employed to show up whenever free agency begins and lock Benning’s phone in the world’s most uncrackable safe. 

Or, at the very least, just keep him away from a microphone. Because the Canucks spent the entire offseason to this point crying poor. And, you know what? They actually backed up their words when the doors opened on Friday, declining to issue Troy Stecher a qualifying offer while allowing both Tyler Toffoli and Jacob Markstrom to test the market for themselves, as well. 

This was done, apparently, due to the team’s lack of cap room. And for the most part, it made sense. The Canucks were already close to the ceiling as it was and lucrative extensions for Elias Pettersson and Quinn Hughes are on the horizon at season’s end, with both deals needing to be squeezed under an expectedly flat cap. 

So why, then, would Benning eagerly usher those key pieces out the door before turning around to give a clearly washed Braden Holtby $4.3 million for two years? 

Can someone good at the economy please answer this? My family is dying. 

The Canucks’ contention window is open now, by the way. As in, right now. Yes, this is a team loaded with young talent, and that’s all well and good. But the tight cap calamity Vancouver has locked themselves into — one currently being alleviated by the value of Pettersson and Hughes’s ELCs that are set to expire — has sped up their timeline expeditiously. 

Benning needs his group to win now. And losing your starting goaltender, along with a winger who fit splendidly into your lineup whose services cost a second-round pick in the deepest draft in years (among other assets) and a young, effective right-shot defenceman doesn’t exactly help that case. 

Those losses would be bad enough on their own. But allowing them to happen just to sign a steeply declining goaltender who also happens to be both worse and older than the one you let walk, though? That’s blasphemous. 

Winner: Toronto Maple Leafs

It wasn’t the sexy, Alex Pietrangelo-themed splash some Leafs fans were hoping for, but Kyle Dubas nonetheless exited day one of free agency having addressed the two biggest flaws on his roster. 

Signing TJ Brodie for four years at $5 million per was the highlight of the day, as it should be. Brodie is a legitimate top-four defenceman, someone who can munch minutes on the right side, put up a few points while at it and, most importantly, be trusted in the dying minutes to defend a lead. 

Frankly, his value is pretty cut-and-dry. It’s the Leafs’ other signing that warrants more attention.

Wayne Simmonds for one year at $1.5 million is tidy business. Now, on the surface, Simmonds looks like a player in decline. And he is, don’t get me wrong. The Scarborough native’s point totals have dipped consistently year-to-year ever since 2015-16, and ultimately culminated in a 2019-20 campaign featuring a mere eight goals and 24 points. 

Do you want to know what else Simmonds looked like, though? This guy. 

If you were too lazy to click that link, Simmonds has been playing the past few season remarkably, profoundly banged. In 2017-18, for example, Simmonds missed only seven games despite playing with a torn pelvis, which then led to a pulled groin, which was then followed up by a fractured ankle and, finally, neatly rounded out by a torn ligament in his hand. 

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Add three more years of wear and tear on top of that, and I’m surprised the guy could get out of bed. 

In normal circumstances, the NHL’s four-month offseason wouldn’t be nearly enough time to rehab from all that. But as every single commercial will tell you, these are not normal circumstances. Simmonds hasn’t played hockey since mid-March, meaning that the 32-year-old will now report to Leafs training camp (whenever it opens, that is) following a nine-month break. That’s nine months to heal; nine months to train; nine months prepare for the rigours of a full season. It’s going to help. 

Also, it’s only $1.5 million we’re talking about here. Bargain. 

Loser: Tyler Johnson 

Listing someone coming off a Stanley Cup who is set to make $5 million per year until 2023 as a “loser” is tough. But, man. Tyler Johnson did not win on Friday.

Everyone knew the Lightning were trade scouring the market for someone to take Johnson. Johnson himself was even aware that his days in Tampa were numbered, with multiple reports suggesting that the two sides had in fact been working together in the hopes of finding a solution with mutual benefit. 

Johnson’s full no-move clause made that tough, of course, but things seemed headed towards an amicable end. 

Then, this happened. 

Didn’t see that one coming. 

Johnson might not be the player he once was, but that doesn’t change the fact that he has a full NMC negotiated into his contract to explicitly prevent the Lightning from shipping him out of town without his consent. At least, that’s what he thought. Because yesterday Julien BriseBois somehow managed to bypass that and put Johnson up for bid to all 30 other NHL teams. And to bruise the ego even more, none of those 30 teams saw adding Johnson to their roster for free as a worthwhile venture. 

Yeah, he lost. 

Winner: Edmonton Oilers 

The Edmonton Oilers closed the book on some pretty tidy business on Friday. It’s hard to argue with any of their moves. 

Re-signing Tyler Ennis at one-year, $1 million not only allows Ken Holland to retain a sneakily-effective middle-six winger at a reasonable price, but it means he won’t be lighting the draft pick with which he paid to acquire Ennis at this year’s deadline on fire — like he did with Andreas Athanasiou days prior. Coaxing prodigal son Jesse Puljujarvi back to town on a two-year deal at $1.75 million per is a win for the organization on the whole and accomplishes much of the same, albeit with higher stakes and upside given Puljujarvi’s draft pedigree and potential ceiling. Anton Forsberg at one-year, $700,000 gives the Oilers a serviceable third goalie who can be called upon when needed. 

And then there’s the main entree. The piece-de-resistance: Kyle Turris. 

Turris draws a lot of similarities to a guy like Derick Brassard. Both are centres in their early-to-mid 30’s with production once hovering around the 40-to-60-point range whose careers teetered recently on the precipice of oblivion. Brassard looked more or less washed after bouncing around between three different teams in the 2018-19 season and signed a bargain-basement one-year, $1.2 million with the Islanders that summer. Fresh off a trip to the Eastern Conference Finals, Brassard is considered a successful reclamation project. Except, last season, the supposedly useless Turris put up one fewer point than Brassard did in four fewer games — 31 in 62 contests compared to 32 in 66. 

Even if he doesn’t “bounce back” and simply replicates that exact total, nabbing Turris — who is two years younger than Brassard, by the way — for $1.65 million is great value. 

Loser: Ottawa Senators

What a way to spoil the fun. 

Riding high following an exhilarating performance at this week’s draft, the Senators wasted no time in reminding their fans of the misery to which they have become all too accustomed. 

Trading a 2021 fifth-round pick for Erik Gudbranson — one of the worst analytical defensemen in hockey — when Ryan Murray (among the best analytical d-men in the league) was dealt to New Jersey hours later for the exact same price is a case of asset management so putrid it should be punished by law. It happened on Thursday but I’m still going to count it. It’s that bad. 

Allowing noted real-life superhero Mark Borowiecki to walk over to Nashville and sign at half of Gudbranson’s price for only two years should be the midterm. And following that calamity up by handing Matt Murray a four year deal with a $6.25 million AAV in a market littered with better goaltenders at cheaper rates should be the final exam. 

Never stop being you, Ottawa. You’re such good TV. 

Winner: Henrik Lundqvist 

The guy gets to keep his Manhattan apartment, hop over to a divisional rival, cash $5.5 million from his former employer along with $1.5 million from his current one all while spending the twilight year(s) of his career chasing a Cup with Alexander Ovechkin & Co. 

One human should not be allowed to win this much at life. Leave some for the rest of us, Hank.

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