Real Kyper vs. Bourne: How should Maple Leafs approach the trade market?

New this season, Nick Kypreos and Justin Bourne from Sportsnet 590 The FAN's Real Kyper and Bourne will debate two questions around the Maple Leafs or the league at large once a month. Their passionate producer, Sam McKee, will round it out by giving his take as the certified Leafs fan of the bunch.

Today's questions both focus on the Leafs, specifically what their outlook should be on the trade market, and what the guys are thinking about Auston Matthews' play so far.

What should Toronto’s trade philosophy be this season?

Kyper: The Leafs’ No. 1 priority should be simple. Protect the organization’s scarce draft picks and prospects at all costs.

It should frighten Leafs fans hearing Elliotte Friedman’s report disclosing that Toronto is open to parting with premium assets, including future first-round picks. We have seen this movie before. There has been enough damage done with that philosophy for over 10 years. From trading a second-round pick for Tomas Plekanec, to moving a first-rounder for Nick Foligno, multiple picks for Ryan O'Reilly, or Fraser Minten and a first-rounder for Brandon Carlo, it is clear there are no guarantees for high cost trades. 

Don’t get me wrong, that doesn’t mean the Leafs shouldn’t make another trade this season. What it does mean is that you can’t keep thinking the next trade is the one that will finally get Toronto over the finish line. GM John Chayka has lifted the level of compete out of the dumpster from last season, and for that he should be commended. But he also did it without strengthening his asset pool. 

Saying that, after just 15 games, it’s still unclear what talent they could get in exchange for the cherished few premium assets they have left. 

Now is the time for discipline and self-awareness until the holes that need to be filled are crystal clear. That doesn’t mean I’m against any trading this season, but we can’t forget that as far as future assets go, the next five years matter. Be aware of the temptation to make a quick trade that looks like an opportunity only to find it’s a trap instead. As the saying goes, sometimes the best trade is the one you don’t make.

Bourne: This is all well and good, but of course the problem is that it’s akin to playing poker and betting large before the flop, raising a bunch of your chips after, seeing the turn card…and just folding.

Like it or not, they’ve come this far, and so the Leafs are pot committed here. 

If you don’t play poker, I’m just pointing out that the Leafs have spent real assets to get back to a competitive level, and now that they’re better, they’ve gotta go further and make the playoffs (otherwise what was the point of all that?). To pick just one reason, showing Auston Matthews they’re going to be competitive should encourage him to re-sign, and that would help avoid what could become a long and painstaking rebuild.

Pulling up now is a good way to get lodged in the mushy middle, picking in the middle, and staying in the middle.

The other problem there is that they don’t even have their own pick in the first round at all in the summers of 2027 and 2028 (they do have Colorado's 2027), so falling short of the playoffs today to “conserve assets” just means you’re both failing now, and failing later. There’s pressure to compete now, and the arrival of Easton Cowan and Gavin McKenna makes it more sustainable and worthwhile.

So, I’m not advocating for trading the aforementioned Cowan, they simply can’t do that. But they may have to be willing to trade the likes of Ben Danford, Artur Akhtyamov, Tinus Luc Koblar, second-rounders or even a distant first if it means getting someone on defence with term who solves a problem. They’ve come too far to fold now.

Kyper: JB, I understand the poker comparison, but “pot committed” is often just another way of thinking like a gambler who believes he’s one hand away from beating the house. 

The Leafs still need to pay the price for all their trade misses over the years. This year, next year, the year after, but the fiddler always gets paid.

It’s better to acknowledge today that those assets already spent cannot be recovered “with one winning hand” and the faster fans realize and embrace this, the better. 

If the Leafs continue to try and trade multiple “premium assets” as is being suggested, for a defenceman who merely fills a hole, they run the risk of buying another short-term solution while weakening the organization’s ability to sustain longer-term success.

Outside Cowan and McKenna, many teams think the Leafs do not have “premium assets” anyway. 

That Colorado first acquired in the Nic Roy trade isn’t considered a premium asset. It would need to be a top 10 or 12 pick to be one. The names you mention JB, like Danford, Akhtyamov, and Koblar, may have upside for another club that’s no different than Nikita Grebenkin did for the Flyers when they gave up Scott Laughton to the Leafs. 

Now JB, if the Leafs can steal a good defenceman with contract term and playoff impact for a run without upsetting the apple cart, then go for it.

But if the choice is between making a marginal upgrade and preserving flexibility, walking away isn’t folding. It’s refusing to chase a bad hand simply because you’ve already invested in the game.

Sam McKee: If there’s one thing I’m sure of with the Toronto Maple Leafs’ trade philosophy it’s this: if they trade Cowan I’ll lose my mind. Over the Matthews era, this organization has lost a lot of heart and soul guys: Nazem Kadri, Zach Hyman and Connor Brown, just to name a few. And now it’s looking like Fraser Minten can be added to that group. Why pay someone like Hyman $5.5 million when you can pay Ondrej Kase, Nick Ritchie and Petr Mrazek a combined $7.5 million instead! 

Woof. Do not trade Cowan. He could be this organization’s next captain.  

This Leafs team is incredibly fun right now and feels like a defenceman away from being a sure-fire playoff team, so I think they should be willing to add. The only real piece I’m down to trade is the Colorado first-rounder, which may end up having a touch more value – the Avs are sixth in the West by points percentage. If you can get a decent defenceman for that pick I’d be happy to make that deal. 

I don’t want to trade Danford unless it’s for a more elite piece, but I’m not 100 per cent sure he has the same value around the league that Leafs fans think he does.

Ultimately if you can add a good defenceman with that Colorado pick then do it, but outside of that let these guys develop a bit before you send out the next Fraser Minten.

Is Auston Matthews all the way back?

Bourne: I don't think there's any question that the answer is a definitive yes. 

Now, people are going to have plenty of other questions: can he stay healthy after a few years of looking hampered, that's going to matter. Is he going to be with the team long-term, sure, that's in the back of people's minds too.

But after the past couple seasons, this question became legitimate, as he fell below a point-per-game pace and didn't seem to have pop in his step or his usual physical dynamism. Even his unique release and dangerous shot seemed off. 

We may have only played less than 20 per cent of the season, but everything that Matthews was doing during his Hart Trophy year is back to elite levels. He's scoring goals at a clip that would threaten 60 (and his expected goals are even higher), he's skating faster and shooting it harder, but the biggest tell that he's all the way back is that he's top-five in the league in puck battles won. He's dominating possession low and earning offensive zone time and chances for his linemates. He's passing the puck and defending well too. He's a force.

So while I don't think players at 29 years old suddenly regain the physical abilities they had at 24, they can find new ways to impose their will on the game, and so far Matthews has not just done that, he's eased fears that he wouldn't physically be able to do it ever again. So simple conclusion for me is that yes, he's back-back.

Kyper: No he is not, yet.  

There is no question Matthews looks much better. He is skating with more purpose, shooting with greater confidence, and finding ways to influence games beyond simply scoring goals. 

Those are very encouraging signs for the Leafs and for a player who has spent much of the past season and a half looking like a diminished version of himself.

But “better” is not the same as “all the way back” for me. 

That distinction matters. Matthews had a quiet night in Calgary on Monday, and those types of performances have been far too common over the past two seasons. One shot on goal in a very uninspiring loss. 

Even his impressive early-season numbers do not instantly erase a very lengthy stretch in which his impact has faded for entire games and sometimes entire weeks.

Do his past injuries explain part of what happened to him the past couple years? Absolutely. 

Matthews has clearly dealt with physical issues, and it would be unfair to ignore that. But explanations are not the same as proof that his previous issues are all behind him this early in a season. 

Until he stays healthy for a prolonged period and consistently drives play over meaningful stretches, this question remains open for me. Fifteen games isn’t enough time to declare a complete return to his Hart Trophy form any more than a slow start would proclaim him washed up. 

A strong start can be promising, but it’s still incomplete. Matthews’ next challenge is to show that his intensity, skating, puck battles, defensive commitment and offensive dominance can hold up night after night and not just appear in short bursts.  

For me, Matthews will be “all the way back” and returned to his prior dominance when his performance consistently leads the Maple Leafs against the best teams in the Atlantic Division and once again puts the team on solid playoff footing like his prior scoring numbers did. 

That is the standard set during his prime years and the one he must attain again.

Matthews is now at a place in his career where he does not need to run toe-to-toe with Connor McDavid in production, but he does need to re-establish himself as the irrefutable force of the Maple Leafs. And not just sometimes…all times.      

Matthews’ improvement so far this season is real, as JB suggests. But the verdict on being all the way back is far from final.

Bourne: I think you make a couple good points in there Kyp, particularly the question about Matthews’ ability to sustain this output, which takes a healthy body to do. He used to be able to do that. Can he this year? Well, we'll see. It's at least nice that he can get to a level that, if sustained, would feel like "back."

But what aren't fair points: that off-nights somehow void the idea that he's "back" (let alone that these nights have happened for a "very lengthy stretch," as we're 15 games into the year), or that the team being down the standings somehow takes away from his form. 

Kyp I did the radio show with you during Matthews’ Hart Trophy season, and I know for sure you felt there were plenty of nights he wasn't impactful. And I also think that when anyone watches a star play 82 (or 84) times, you feel like they're unique in that their performance can be up and down, but watch just about any star in the league. You'll find quiet nights from David Pastrnak, from Kirill Kaprizov, even that absolute terror that is Connor McDavid has quieter nights (though this year he only gets two points on those nights).

But as for the team stuff, the Leafs are near elite when Matthews is on the ice, and near a bottom-feeder when he isn't. This isn't basketball where he can play 48 minutes and they can get him the ball in the big moments. And you know as well as anyone there's only so much any one player can do for a flawed roster. The question is whether he's "back," not whether he's perfect. 

I'd say we're right back to where we were a few years ago, arguing if his dominance is dominant in the right ways, if he can keep it up, if his individual success is good for the team, etc. By that vibe alone, to me it sure feels an awful lot like we -- and he -- are fully back here.

Sam McKee: I am absolutely stunned to see Kyper say Matthews is not all the way back (not stunned). I not only think he’s back, I think there’s an argument for him being better all-around then he’s ever been.

What's jumped out to me this year isn’t even an on-ice thing. He seems to have taken a massive leap as a captain. I’m not sure what to attribute this to. Maybe it’s former captain Mats Sundin entering the fray, but Matthews’ change in tone has been stark. When Cowan was hard on himself after the Calgary loss, Matthews went out of his way to shift the blame to himself and talk about winning and losing as a team. I’m not sure we would have seen that in years past and that stuff matters to fans. The post-game tone for the past decade has been a huge sticking point with Leafs Nation. Accountability goes a long way with this fanbase.

As far as his on-ice stuff goes — puck pursuit, weight on pucks, using his body — he’s looking to setup his linemates more and he’s shooting it in the net at an elite level again. His defence has never been a question mark and the job he did against McDavid was spectacular. It’s been a delight to watch.

I have to be totally honest: I’m not sure I’d ever say that Auston is back, but I am willing to say he’s back and maybe better than ever.