Winners, Losers and the Toronto Maple Leafs: Evaluating the NHL Off-Season

For the Toronto Maple Leafs, the NHL off-season has been going on for over two months.

Despite that, the real off-season didn't really begin until the Edmonton Oilers (much to the Toronto Maple Leafs delight) failed to fully comeback and defeat the Florida Panthers.

There was a busy week leading up to the draft, the draft itself and then free-agency shortly after. Though perhaps not as busy as we would have liked, being fans of the Leafs.

Now that we have seen the dust settle, it's time to evaluate what happened.

Teams like Tampa, Nashville and Washington made big moves, while some teams - the Calgary Flames, the Anaheim Ducks - barely seemed to do anything.

Other teams, like Seattle, were just confusing.

As we know, the Leafs tried and failed to upgrade their goalie situation then took a huge swing on Chris Tanev and a couple other baffling decisions we will get to - but how did they do comparatively?

Do the Leafs end up in the winners or the loser when compared to the rest of the NHL?

Let's find out.

The Kings and Clear-Cut Winners of the Off-Season

The Edmonton Oilers celebrated their appearance in the Stanley Cup Final (which was awesome and hopefully no one has been spinning being the runner up as a negative) by making the best move possible for their franchise:

Moving on from Ken Holland.

Ken Holland is one of the NHL's worst GMs but he always falls backwards into success, which must be frustrating for less lucky general managers, but whoever they've got running their team in the interim should really have the job full time.

Most teams who are good enough to make the Finals in a cap-league get ravished in the off-season but the Oilers managed to retain everyone and get better somehow.

They re-signed Corey Perry, Adam Henrique and Mattias Janmark all on very reasonable extensions.

Then they signed Victor Arvidsson, and Jeff Skinner to value-deals that make them better.

The trade with Buffalo which landed then a top-prospect for a mid-range non-star player in Ryan McLeod was a perfect cherry on top of a near perfect off-season.

The Oilers will once again be one of the best teams in the NHL - probably the very best - and should have no trouble repeating as Western Conference Champions.

To be honest, no NHL team came close the Oilers who won the NHL off-season by a country mile.

Another Misguided Team

The Washington Capitals were incredibly lucky to make the playoffs despite being a terrible team, and like the Predators, they have a misguided and romantic idea of remaining competitive while the best player in their franchise history, in this case, Alex Ovechkin, is still around.

Can't blame em, but it won't work.

I like Pierre-Luc Dubois as a high-risk high-reward play, but overall all they did was add expensive, mid-range pieces that won't really do anything.

Andrew Mangiapane is a decent middle-six guy but you shouldn't pay for mid-range players in the NHL because they have, by far, the lowest chance of returning value on their contracts.

$6 million on an expiring contract isn't the worst, but that 35 goal season was clearly a mirage.

Logan Thompson is a name, but that's about it.

Jacob Chychrun was acquired on the cheap, and Matt Roy will make any team better, but these aren't likely to be high-impact additions.

The Capitals got a lot more name-brand recognition but zero sure-fire stars. They could hit the lotto and get a star season out of Chychrun, Roy, Mangiapane and Dubois and have a very competitive season, which I guess is the goal, but there is almost no chance of this team wining a Cup.

As for even making the Playoffs, that's going to be a long-shot in itself.

The Leafs, Panthers, Rangers, Devils and Hurricanes are all but absolute locks to make the playoffs.

That leaves just three spots for Washington to sneak in, and the Sabres and Senators are both up and coming fast. The Bruins and Lightning have better rosters than Washington does, even with their improvements and so, too, do the Penguins.

The Capitals have no choice to try and win with the aging Ovechkin but it's not gonna work. Like the Predators they are extremely misguided.

General Winners

The Oilers, obviously, but other teams have had good summers too.

The Winnipeg Jets, I mean the Phoenix, excuse me, Arizona Coyotes....er Utah Coyotes had a very nice summer adding arguably the single best player who changed teams in Mikhail Sergachev.

It's a loser move to call them the Utah HC but you can't go wrong whenever you add a top pairing, number-one defenseman to your team. Adding John Marino doesn't hurt either.

The Sabres had a quite and solid summer adding Ryan Mcleod and players like Zucker and Lafferty that will make their bottom-six a lot better. I think they are on the verge of competing and would have liked to see a bigger addition, but they have $15 million in cap space and can add in-season, like I advocated the Leafs to do because there are always unexpected star players available at the deadline while waiting allows you to audition your prospects and see what you have.

Ottawa, adding Linus Ullmark on the cheap was a brilliant move that makes up for giving Chychrun away for nothing. You can't help but be a winner when you add a top goalie.

The Devils added Jacob Markstrom (and Brenden Dillon and Tomas Tatar and Brett Pesce) and are obviously a way better team because of it.\

Boston added Nikita Zadorov who was my biggest hope for the Leafs, and I think that's really going to prove to be a genius signing.

Now, on to the losers.

General Losers

I think both Nashville and Washington are losers for their misguided approaches to roster building around old star players.

I think Chicago is a loser for not realizing the advantage of having Connor Bedard on an entry-level deal providing probably 10-15 million in value this year. You have to try to win while your franchise players is so cheap and they aren't.

The Kraken sound like they were smoking Kraken when they signed Chandler Stepheson to that insane contract that is like $2 million annually too high.

The Vancouver Canucks inexplicably re-signed Tyler Myers and then made the exact moves that you would expect a team that would do that would make.

Jake DeBrusk and Danton Heinen are the kind of mid-range additions that are expensive and tend to hurt more than they help. Both are nice players, but I'm better their combined salaries prove to be a huge mistake. The defense after Quinn Hughes and Filip Hronek is pretty suspect and when half of your blue-line is Myers, Deharnais and Forbert, well good luck with that.

Vancouver also lost Nikita Zadorov which will prove regrettable.

The Colorado Avalanche have a huge wide-open window to win another Stanley Cup, but they aren't helping themselves much with such a bad off-season. They lost Sean Walker and on one they brought in is replacing him.

But the biggest loser? The NHL team that had the worst summer?

Do you even have to ask?

The Worst Summer of Any Team In the NHL

It's not that the Toronto Maple Leafs made bad moves, it's that they do not understand the concept of risk vs reward.

Want to give Timothy Liljegren $3 million? Fine, but get some cheap years out of him. Only 2 years? What are they thinking? If they gave him $4 million but got some extra years that would clearly at least give them the chance of getting some team-friendly years.

If Liljegren ends up being worth the $3 million, they will just have to immediately extend or trade him, which means it's a bad contract.

Same exact thing with Joseph Woll. They are betting that a tandem of "maybes" is worth risking Auston Matthews prime over, but if it actually works out they won't get much value because Woll's deal is only for three years.

Woll has combined to play about a full season over the last four years and is an extreme injury risk, so giving him a guaranteed contract that doesn't the team a chance to cash in if they bet right just makes no sense.

Also, Nick Robertson, their top prospect, more or less, has asked for a trade.

The Leafs entered the off-season with a clear need to finally pair Auston Matthews and Mitch Marner with one of the NHL's best goalies. They failed.

They needed to upgrade on Pontus Holmber at 3C. They failed.

In fact, they lost Tyler Bertuzzi and their forward lines took a huge hit. If Robertson is also gone, that's two impact players lost and zero incoming.

They gave an objectively bad contract to Max Domi that was insanely long and which no other team would likely have even considered. Like all Leafs contracts, it begs the question "who were they negotiating against?"

The Leafs also needed to clear cap space by moving out the dead-weight on their roster but they also failed, as of now anyways, to do that.

The only thing they accomplished was improving their blue-line which they did by giving an injury prone 34 year-old a six-year contract, and doubling the salary of a 33 year-old third pairing vet they hope can now play in the top four. Apparently the Leafs are not interested in things like "up-side" and "value."

But their biggest problem is that they have no appetite for risk. The entire Toronto Maple Leafs front-office needs to sign up for a course in risk vs reward management.

Weirdly, this could all work out because, like Edmonton, the pieces already in place are so good even a brutally unqualified GM can't screw it up too badly.