A decision on Ryan O'Reilly's future with the Maple Leafs will trickle down to the rest of the lineup and the many holes to fill.
theathletic.com
I surveyed a few agents this week, and they all explained that term would be a big part of any O’Reilly extension, given his age and tough season in St. Louis. But you’re likely looking at somewhere between three and five years, with the cap hit lower the longer you decide to go.
I also think O’Reilly might be willing to offer a little bit of a discount to either the Blues or Leafs, assuming his time in Toronto the rest of this season goes well. So perhaps that number shaves down a little bit.
But this isn’t going to be a Giordano/Spezza-like hometown discount.
Regardless, I think these numbers are in the right ballpark, based on comparables and talking to people around the league about what would make sense here, assuming this turns into a longer-term marriage.
If O’Reilly stays, what then?
If O’Reilly signs for around $4.5 million or so, it would leave the Leafs with roughly $9 million in cap space and potentially (likely?) out on bringing back Bunting. It would leave a roster badly in need of another winger for Auston Matthews and replacements for Kerfoot, Engvall, Kampf, etc., down the lineup.
This is where things devolve into even murkier hypotheticals that we can’t really answer at the moment. Because if the Leafs lose in the first round, the front office may well be deconstructed. With a new GM in place, the first order of business would be deciding how to handle the fact both Matthews and William Nylander will be entering the final year of their contracts.
If they’re not going to be extended, there’s a world where moving a major piece or two out becomes a very real probability. This makes all the above cap gymnastics kind of irrelevant.
This is frankly a likely scenario if this group doesn’t have playoff success, and there’s new management in place.
If we set aside the mass upheaval timeline, however, keeping O’Reilly makes a lot of sense, especially at that number. For one, it allows Tavares to settle in on the wing, which extends his effectiveness through the end of his contract.
The Leafs’ contention window is also such that any age-related decline from O’Reilly towards the end of a contract like this shouldn’t be the guiding concern.
To keep O’Reilly, however, the Leafs would have to get creative in filling out their roster. Heck, they’re going to have to be creative no matter what this summer.
Moving on from Bunting would mean they would have to go bargain-hunting for another top-six forward. They would also have to think long and hard about if they felt their blue line, as constructed, is good enough, and whether they wanted to go into another season with Samsonov and Murray as the goalie tandem. Especially with how many games Murray has missed due to injury the past two years.
Without many high-end prospects coming, save for perhaps Matthew Knies, restocking the forward group on the cheap is also going to be a challenge.
All that said, there’s a path here that makes a lot of sense to make the O’Reilly trade a longer-term arrangement than a deadline rental.
Especially so if these promising early returns last deep into the spring.