Going into the offseason, the Toronto Maple Leafs have many fixed pieces on their roster. They would have very little trouble icing almost exactly the same group of players, if that were what they wanted to do, and most of their core pieces are under contract. However, the Leafs probably do not want to tread water. They want to improve, and make a leap into the league’s top tier.

Let’s look at the key decisions the Leafs’ FO will make.

Do the Leafs acquire a top-four defenceman? Do the Leafs trade James van Riemsdyk? Do the Leafs trade Tyler Bozak Do the Leafs re-sign Brian Boyle? Do the Leafs attempt to replace Zach Hyman? Do the Leafs re-sign Curtis McElhinney?

I am assuming the Leafs will re-sign RFAs Connor Brown, Zach Hyman, and Nikita Zaitsev; it is extremely rare for a team that is not capped out to lose RFAs it wants to keep, and the Leafs clearly value all three players greatly. I have also assumed that the Leafs will not lose any of their top-nine forwards or top-four defenders in the expansion draft, because there’s no reason they’d have to do that unless they wanted to. Finally, I have assumed that Matt Martin will remain in his role as 4LW, because all the evidence is that this is what will happen.

1. A Top-Four Defenceman

The most glaring need the Leafs have is to upgrade their defence group. Jake Gardiner, Morgan Rielly, and Nikita Zaitsev appear to be a clear top three, while Connor Carrick, Martin Marincin, and Matt Hunwick have all floated in and out. Gardiner and Rielly both usually play on the left side, and both have played with the right-shooting Zaitsev. Earlier in the season Morgan Rielly was taking the toughest competition, while Gardiner has taken over in recent weeks. At any rate, the ideal would be a right-shooting defender who can cut down substantially on shots and chances against, which are a bleeding weakness for this team. (But heads up: no one player is going to be able to fix that problem entirely, because it’s a collective problem.)

I surveyed several candidates for this upgrade in the middle of the year, and the same list of names is still applicable. Capitals rental Kevin Shattenkirk seems very unlikely to re-sign in Washington, both because they would struggle to afford his cap hit and because he’s currently playing on their third pair. He’s the only major upgrade who would interest me as a free-agent defender this summer; while he would be expensive, it’s also noteworthy that he wouldn’t cost assets—something people seem to overlook when accounting for price. The Leafs have the money to make this signing, if they want to.

Beyond that, you have the trade options: a quality defensive RHD like Anaheim’s Josh Manson or Vancouver’s Chris Tanev would make sense, or Toronto could try to make a very expensive play for Winnipeg’s Jacob Trouba. All of these three, or Shattenkirk, would immediately upgrade Toronto’s defence, and could form a plausible first pairing with Gardiner or Rielly.

Of course, you never know who might or might not be available—and knowing Toronto GM Lou Lamoriello, if there’s a big deal being made, we won’t know until it’s done.

2. James van Riemsdyk

Left-winger James van Riemsdyk, who will turn 28 in a couple of weeks, is entering the final year of a contract that will pay him $4.25M, after which he will be an unrestricted free agent. Before we get going on this, it’s worth noting that JVR has a limited NTC—he has a list of ten teams to whom he will not accept a trade. This may complicate any effort to trade him, but we don’t know who’s on that list or JVR’s willingness to waive the clause, so we can’t do more than note it’s there.

JVR scored 29 goals this season, his fifth consecutive year producing in the 25-31 range for goals per game. He’s a big power forward with excellent hands in close, and that kind of net-front and finishing ability makes him a credible fit for almost any playmaker you want to name. His defence is less than impressive, but goals are goals. JVR is almost certainly going to get a pricey, and lengthy, deal.

Toronto has a tough decision to make with van Riemsdyk, who is one of the longest-serving Leafs on a young roster, and who helps provide that incredible offensive depth they’ve enjoyed this year. With three star rookies soon to be requiring big raises, though, a JVR extension may be a luxury the Leafs cannot afford, although JVR has said he’s interesting in staying. If the Leafs can’t re-sign him—van Riemsdyk would be in a position to sign an extension as of July 1st—should the Leafs keep him around to run their best possible lineup next year? Or should they flip him for assets while they can?

It’s easy to combine this question with the first one, and many proposals along the lines of JVR-to-Anaheim have been thrown around. It’s hard to say how credible any one of these is, but JVR would certainly have value to many teams. If the Leafs were to use a retained salary slot on the final season of JVR’s deal, they could offer a 30-goal scorer for a year at $2.2M—an incredible bargain for a team trying to make a Cup run with limited cap room. It’s worth noting that any team acquiring JVR before the expansion draft would have to protect him, though.

Related Trading JVR Will Not Solve the Leafs Blueline Woes

As for the Leafs, should they ship out a winger and not bring one in, a job opens up. Heavy-shooting winger Josh Leivo showed impressive production in short stretches in a depth role for the Leafs, although Mike Babcock has proven reluctant to play him and he might be claimed in the expansion draft. Nikita Soshnikov always seemed to have more energy than was being well-used in his 4RW job, while LW Brendan Leipsic has put together a great agitating-and-scoring year for the Marlies. The most obvious candidate, though, would be speedster Kasperi Kapanen—if he’s able to play off-wing, he’s been excellent both in the AHL and in an NHL depth role this season, and he’s clearly ready for a promotion.

(Or if you want to go wild, Ilya Kovalchuk is rumoured to want to come back from the KHL...)

JVR seems like such obvious trade bait—on a team with great offence and poor defence, he’s the most obvious way to deal from a surplus—that I feel like I ought to add one thing. A JVR trade might be the right move for this team, but it won’t be painless. When your team loses a 30-goal man—even a team with a lot of good forwards—you’re going to notice the absence.

3. Tyler Bozak

Leafs 3C Tyler Bozak has finally seemed to get his due this year, after being the subject of endless debates through the Dave Nonis era. Bozak is a defensively shakey, but offensively very useful, opportunistic centre with a strength at faceoffs. He finally broke through the 50-point barrier this year, setting a career high of 55 points at the late age of 31.

That age, and his contract status, raise questions. Bozak has shown no signs of decline yet, but he’s in the final year of a deal with a $4.2M cap hit and a modified NTC (Bozak submits a list of 12 teams he will accept a trade to.) Is it time to deal Bozak to a team looking for a productive centre?

If the Leafs deal Bozak, the obvious move will be to move star RW William Nylander to third-line centre, and to move Kasperi Kapanen up to a higher right wing slot. Nylander has been outstanding as a 20-year-old 1RW, and probably has the talent to function very well as a sheltered top-nine centre. On the other hand, Nylander and 1C Auston Matthews have had outstanding chemistry this season, forming one of the deadliest lines in the NHL with Zach Hyman. We can move Bozak, but as our own Arvind has pointed out, this would not be a lossless transition.

If this team is as close to contention as it looked against the Capitals, maybe another year of Bozak isn’t a bad idea—keep the forward lineup intact, accept that the rebuild has gone ahead of pace, and make a serious run in 2017-18 after upgrading on D.

A third option would be to flip Bozak and make a bold UFA signing or trade. It’s not the strongest market, but if the Leafs really want to go for it, veteran Hall of Famer C Joe Thornton is still a very capable playmaker. More exotic options would include KHL star Vadim Shipachyov, who’s alleged to be considering the NHL.

It’s tough to know what the return for Bozak would be in a trade: his numbers are impressive, but he’s usually considered to have been a complementary centre playing with elite wingers in his career (JVR, Phil Kessel, and now Mitch Marner.) Still, 50-point centres are a valuable thing in this league. Somebody would be interested, were Bozie available.

4. Brian Boyle

Toronto’s fourth-line centre job was a source of discontent most of this season. Peter Holland did not fill it to Mike Babcock’s satisfaction, and got traded. Ben Smith was an AHL-calibre centre in an NHL job; so was Frederik Gauthier, though people didn’t want to admit it. Finally, the Leafs traded a second-round pick to Tampa Bay for Brian Boyle at the deadline. While Boyle wasn’t cheap for a rental, old-schoolers, nerds, and Mike Babcock all seem to have been pleased with his work as 4C.

Boyle is such a good 4C, though, that he’s probably going to command somewhat more than a depth salary, and he’s 32 years old. Assuming Boyle does want to stick around in Toronto, rather than return to Tampa Bay—Boyle’s wife Lauren is pregnant with their second child, and the family disruption of moving countries is never small—he might well want term to do so. I would be fine going up a bit financially on AAV to avoid signing Boyle for more than two seasons; what BB and LL would negotiate, I can’t say.

If the Leafs keep Boyle, that makes their fourth-line plans simple for the next couple of years—immovable LW Matt Martin, Boyle, and young player of choice (Nikita Soshnikov?) can work as a fourth line on a competitive team. If they don’t, the Leafs could consider depth veteran Eric Fehr at 4C once his hand recovers, or even moving 3LW Leo Komarov down to 4C. They could also try to make a UFA signing; they had a rumoured interest in KHL centre Vladimir Tkachyov earlier this year.

One popular idea seems misguided to me, though: Bozak as a 4C is a waste of money and talent; putting an offensive opportunist next to defensive basher Matt Martin seems likely to have an oil-and-water result. Whatever the Leafs do, they seem to realize that having Ben Smith as your fourth-line centre is not something a contending team can get away with—and a contending team is now what the Leafs are seeking to become.

5. Zach Hyman

First-line LW Zach Hyman is a gritty, energetic forechecker, a hard worker, and a regular penalty killer (with some debate as to how good he is at that, exactly.) He has a certain role synchronicity with his star rookie linemates, Auston Matthews and William Nylander—while Matthews is the league’s greatest scoring chance machine and Nylander mixes carry-ins, snipes, and elite playmaking, Hyman is the guy who torpedoes into the corner and fights like a bull terrier for the puck. The problem is that Zach Hyman is also the guy who produced only 28 points this season as an even-strength first liner.

The debate over Zach Hyman has been long, combative, and has points on both sides, so I’ll try to quickly summarize. The best argument in favour of Zach Hyman on the top line is that his line is functioning at extremely high effectiveness—very good possession numbers, and phenomenal scoring chance numbers. Mike Babcock argues that since guys like Matthews (who shoots in heavy volume) and Nylander want the puck so much, it makes sense to give them a linemate who will get the puck for them and give it to them. This prevents a conflict of roles, like you might have with another volume shooter, and lets the Leafs put a more offensive winger on another line (JVR is the obvious example for this.) In short: it ain’t broke, don’t fix it.

Against Hyman-as-1LW is the argument that you cannot have a first-line LW who produces so few goals at even strength (6 in the regular season), no matter what else he might be doing. Matthews is a shoot-first player, and always has been, but he is not at all a bad passer or playmaker, and he would certainly get more assists with a linemate who had more offensive finish. In short: maybe it ain’t broke, but it could work a lot better.

The complicating factor in this is cost. I think almost everyone would agree the ideal lineup would upgrade on Zach Hyman; the question is whether the most effective complete lineup the Leafs are actually capable of putting on the ice uses him there. To take one example, if the Leafs were to trade for Colorado’s Gabe Landeskog and put him at 1LW, they would immediately have one of the best first lines in existence. But Landeskog is going to cost considerable assets in a trade and a sizable cap hit.

Is there a middle ground between a pricey trade and status quo? Is there a better move to be made that gives better bang for the buck across the whole lineup, and replaces Zach Hyman, while still leaving cap to upgrade the defence? Maybe. Especially if the upgrade is internal—Kasperi Kapanen might work very well in Hyman’s role based on his elite speed, and he has more offensive finish than Hyman does. But if the Leafs are moving out another forward, Kapanen might be taking a different winger spot instead. The question isn’t “can you imagine a better option than Hyman”, because we all can. The question is, “is this a high enough priority to spend on, if it’s going to cost us?” And to be honest—aside from giving Kapanen an audition for Hyman’s job in training camp (which I think should be considered), I have no idea.

All of this is a long way of saying I think Zach Hyman may well be back in the same job next year: not because there’s no answer to upgrading on him, but because this isn’t the #1 question.

6. Curtis McElhinney

The Leafs appeared to settle their backup goaltending situation late last summer by signing competent netminder Jhonas Enroth. Enroth then had an absolutely atrocious couple of months and wound up being traded to Anaheim, where all failed Leaf goaltenders go. After a couple of outings for minor-leaguer Antoine Bibeau, the Leafs claimed Columbus backup Curtis McElhinney on waivers in January.

McElhinney had a perfectly nice backup showing in the Leafs’ net, winning almost as much as he lost and putting up a save percentage of .914 behind a less-than-ironclad defence. The problem is that McElhinney’s career average is .905 and that he’s about to turn 34 years old. If his work in 21 games this year is not representative of what we can expect from him—and we have reason to suspect it isn’t—Toronto could be facing Enroth redux next fall. For a team that only made the playoffs by one point, and that had to work Freddie Andersen to the bone to do it, that’s not a comfortable risk.

Goaltenders are, as we all know, voodoo, and virtually anything can happen over the tiny sample of 20-35 games we’d be counting on a backup to play. (Needless to say, if Andersen gets injured, we’re probably dead.) However, the Leafs might be well-advised to make a safer backup bet than McElhinney to improve their chances. Hey, I hear Jonathan Bernier is available...or if that brings back bad memories, there are several other options with steadier track records, like Anders Nilsson. The Leafs could even give Garret Sparks another spin.

This may seem like a minor decision, and it may turn out to be. The difference between a good backup goalie year and a bad one can be as little as five or six goals, and nobody can predict how things will shake out with that much precision. But this decision may go a long way in a tight playoff race next year—we can all think of playoff draws that would have been much easier than Washington, and a few more points from our backups could have attained them for us. Toronto should be careful here.

Conclusion

The Leafs have an extremely strong core to build on, and yet this is a critical offseason to maximize its chances going forward. Lots of big decisions on the table, and lots to watch for on our end. If the Leafs play their cards right, they may be genuine contenders in 2017-18...or they may tread water.