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Maple Leafs trade deadline mailbag: Trade targets, prospects, & more

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Photo credit:Mandatory Credit: John E. Sokolowski-USA TODAY Sports
Alex Hobson
1 month ago
Growing up, my Trade Deadline Day experience was like that of many others. I’d come down with a really bad “sickness” on the day of that ensured I stayed home and absorbed seven hours of Bob McKenzie and the rest of the TSN Tradecentre crew. If I didn’t do a good enough job of convincing my parents I was sick, I’d go in for a couple of classes in the morning and sneak home when I knew nobody was there.
My trade deadline plans haven’t really changed, except now, I don’t have to skip school or work to take it in. It usually makes for a couple of entertaining weeks of online discourse leading up to it, and with Brad Treliving at the helm for his first deadline as Leafs GM, I figured there would be no better time to try and hash out some of these questions we have. I sent out a tweet looking for deadline-related questions from followers of mine, and I’ve compiled enough to put together an article looking at some of the biggest burning questions as we head toward March 8th.
Hi Paul, pleasure to have you.
If I’m Treliving in this situation, I’ve been given lots to think about, and I probably do it. If Cowan is off the table, which he should be, I’d try to sway Ron Francis with Topi Niemela. If not Niemela, I’d probably consider sending Fraser Minten back the other way, but even that would have me wary considering the Leafs don’t really have a centre in the system to step up once John Tavares’ contract expires. Larsson having the extra year on his deal after this season is key, and Tanev despite an off-year offensively could probably be rejuvenated on his hometown team pushing for a Cup. It’s a trade that would instantly fill the two most documented holes in their lineup, and as much as I think Minten’s future on this team is important, legitimate postseason success in the short term is more important.
You’re going to find out very quickly that there was a theme to many of the questions I got, so I’m going to stay on topic. The more I think about it, the more I think the Kraken are the perfect trade partner. Ron Francis has a history with both Treliving and the Leafs’ organization as a whole, and they have a number of targets that meet different types. The aforementioned Larsson and Tanev for term options, and guys like Jordan Eberle and Alex Wennberg for pure rental options. There are rentals available on every team, so I do believe the Leafs will pivot back to the Kraken more than once to explore their term options.
It’s hard to say who “won’t cost a first” because teams always value their own players more than other teams will, and that usually results in teams setting their starting point as a first-round pick. Still, that could and usually does end up changing depending on how much of a bidding war there is. Now, if we ignore this factor and go off of players who probably aren’t worth a first at face value, I’d be calling the Columbus Blue Jackets about Andrew Peeke. He’s the same age as Simon Benoit and has two more years at $2.75 million. If he fills a similar role to the one Luke Schenn did last season, there could be some value there.
In terms of checking off all the boxes in this tweet, it’s hard to think of a better match than Will Borgen of the Kraken. He’s right-handed (check), has good size at 6-foot-3 and 204 pounds (check), leads all Kraken defencemen in hits with 146 (check), kills penalties (check), and sits in the NHL’s 91st percentile in the category of top skating speed according to NHL Edge (check). He also makes $2.7 million this year and next (check and check). I think Larsson would be just as good if not a better fit, but Sportsnet’s Elliotte Friedman doesn’t believe the Kraken are interested in moving him. Take that how you will.
Nevertheless, either of these players would be the perfect acquisition on the back end, specifically to play with Morgan Rielly and allow the Leafs to keep running with their newfound bottom-4 in T.J Brodie – Timothy Liljegren and Simon Benoit – Jake McCabe. In Borgen’s case, you could probably tap into the surplus of near-NHL-ready talent in the AHL, guys like Alex Steeves and Nick Abruzzese, and in a perfect world, dodge the first-round pick. Hopefully we were thinking of the same guy.
It’s very tempting. We’ve seen how this Leafs defensive corps has been able to adjust without the services of Rielly, and as the games go by it becomes more and more evident that the addition of a Schenn-type next to Rielly not only gives them a type of player they need, but it has a ripple effect on the rest of the defensive corps. That being said, I don’t see a scenario where Flames’ general manager Craig Conroy wants to trade with Treliving and the Leafs. That said, if there was a cheap two-year extension to follow, it would be hard for me to say no. Tanev is quite literally exactly the type of player they need, and he’s rightfully a hot commodity on the market right now. So, to answer your question, it becomes more acceptable, but it still comes down to how much of a bidding war there is.
As much as I don’t believe this year is the one to go all-in the way they did in acquiring Ryan O’Reilly and Jake McCabe last year, I wouldn’t be satisfied with the Leafs’ deadline if they did nothing. The Leafs have extended their Cup window by five years at least with the extension of Auston Matthews, and to me, you need to at least try to improve the roster whenever you can. No, they probably won’t be after a top-6 centre or a top-2 defenceman, and they probably shouldn’t be. But that right-handed defenceman to play with Rielly is becoming more and more evident of a need for them, and standing pat at this point would be setting them up for another first-round exit. To answer the question simply, as long as they grab that defenceman, I’m fine if they don’t do anything else.
It will all depend on two factors. The cost, and another big one that seems to be flying under the radar – whether said left-handed defenceman can play the right side. If there’s a world where Ferraro will cost less than a first-rounder and can play the right side, I think this deal becomes much more plausible. But, the reality of the Leafs’ situation is that lots of it depends on keeping their non-Rielly pairs together. We’ve seen that Rielly and Brodie as a pair can’t be trusted this season, which takes that option out of the equation, and despite the familiarity there, it’s not worth it to break up the Brodie-Liljegren pair that’s been playing so well lately. I think they have to trade for a defenceman no matter what, even if not a right-handed one, but I think Treliving will do everything in his power to make sure that defenceman can play the right side one way or another.
Need? Probably not. I’m sure that in a perfect world, Treliving gives Sheldon Keefe a reliable, defensively sound centre who can shift one of John Tavares or Max Domi to the wing, but I don’t think that need trumps that of a right-handed defenceman. Especially considering the incoming return of Calle Jarnkrok, I don’t think the Leafs swing a deal like this unless they try to upgrade on someone like Nick Robertson – but even that feels unlikely.
If he was three or four years younger, I’d say the top-six winger potential is there, but at the ripe age of 27, it seems like more of a what-you-see-is-what-you-get situation. That said, he’s definitely proven himself enough to earn a spot in the playoff lineup. He works harder than just about anyone else on the team and can fit on both a scoring line in a power-forward role or on a checking line in the same role. I see him as a bottom-six, third-line guy with placeholder ability in the top-six at most, but crazier things have happened.
I’m going to pivot back to the Kraken one more time here and float Jamie Oleksiak as an option. He leads the team in penalty kill ice time (3:07/g) and blocked shots (134), but he’s left-handed and there would probably need to be some salary retention involved considering he’s owed $4.5 million annually for two more years after this year. If he can play the right side, I’d be taking a long look at him. If not, you’re probably not finding Will Borgen on any trade bait boards, so pivot back to him.
Ah, it wouldn’t be a Leafs mailbag without the never-ending question “What do we do if this team loses in the first round again??”. To put it lightly, I don’t know. It would depend on how they went out, who was to blame, and whether Treliving would feel comfortable enough parting with a core player only one year into his time as GM. That said, he still has a round full of bullets to fire, so I’d imagine it would start with the firing of Keefe along with a big offseason trade to shake the back end. Let’s worry about that when we get there though.

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