Toronto Maple Leafs Biggest Off-Season Question

TORONTO, ON - APRIL 16: Morgan Rielly
TORONTO, ON - APRIL 16: Morgan Rielly

There is one question that looms over all other for the Toronto Maple Leafs this off-season.

Do the Toronto Maple Leafs pay for a legit #1 pairing partner for Morgan Rielly, or do they settle for acquiring some effective but low-cost right handed players to upgrade the blue line?

This could effect the Leafs for a generation. How they answer this question could be the most important thing the new GM – Dubas or whoever – ever does for the team.

Nylander?

Do the Leafs look to trade William Nylander for help on D?  I have thought about this a million times and there is no way I can see this being anything but an idiotic move.  You just don’t move elite players for question marks.

If there is another Seth Jones out there then maybe.  Jones was only 20 when the Jackets got him from the Predators.  Trading for a guy like that makes sense, but it is also the only example of a 20 year old blue-chip sure to become a superstar defenseman being traded for a forwards I could find.

Who in the current NHL is 20 and a near guarantee to be a superstar?

The only other thing that was even close was when the Lightning got Mikhail Sergachev for Jon Drouin, but I don’t think he’s on the Seth Jones level.  Nyander can only be traded if the return is a player they figure to be as good as Seth Jones.

The corollary here is obviously Hall for Larson, which should scare the Leafs from even considering moving Nylander.

Salary Factors

It’s really easy to think that you’ve got it made with Marner and Matthews and that subsequently Nylander is expendable, but I find that line of thinking extremely questionable.  You can never have too many elite players, and Nylander is going to be elite (if he isn’t already).

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He’s every bit as good as Marner and if that’s a couple notches behind Matthews that’s no shame since everyone other than McDavid basically is.

Moving Nyladner, however, is not the only answer. The Leafs are stocked at the wing position and despite how exciting they are as prospects, Kasperi Kapanen and Andreas Johnson are expendable as trade bait if necessary.

While a one-for-one trade is what everyone seems to be talking about, I feel like the Leafs could minimize the risk inherent in trading Nylander by putting together a package of either Kapanen/Johnson, a B-level prospect and one or two first round picks, depending on the player their targeting.

This would still be risky, but at least Nylander isn’t traded.  Then again, there’s the pesky fact that the Leafs must find a way in which to keep Nylander, Matthews and Marner on reasonable long term cap-hits, which itself may force the trade of Nylander.

Which brings us back to the main question: is it better to go for the big fish, or is it better to target a couple effective yet cheaper options?

Next: Bad Choices for GM

Do the Leafs chase the likes of Erik Karlsson or Oliver Ekman-Larsson?  Or do they settle for someone like Mark Pysyk?

How the next GM chooses to answer this question may define the Toronto Maple Leafs for years to come.