Confirmed with Link: Leafs have acquired Ryan O’Reilly, Noel Acciari & Josh Pillar in a three-team trade with STL and MIN

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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.
Of course not given hes 32 not 36/37+. I would be fine with a a 3-4yr deal at 5.5-6m, followed by one year home discounts until he retires.
 
The issue is choosing Jarnkrok over Acciardi.

It's not necessarily as straight forward as that. Sometimes players in free agents will opt to sign with another team just because they felt like it for some reason or another.

Just beacuse the Leafs potentially had interest in a player doesn't mean he would have been a lock to sign
 
It's not necessarily as straight forward as that. Sometimes players in free agents will opt to sign with another team just because they felt like it for some reason or another.

Just beacuse the Leafs potentially had interest in a player doesn't mean he would have been a lock to sign
It’s always weird that people don’t seem to understand that things aren’t just unilateral. It’s the kind of stuff you pick up on pretty young, no?
 
It's not necessarily as straight forward as that. Sometimes players in free agents will opt to sign with another team just because they felt like it for some reason or another.

Just beacuse the Leafs potentially had interest in a player doesn't mean he would have been a lock to sign

Not only that, but the Leafs needed depth scoring more than a physical 4th line presence. It isn’t absurd to sign Jarnkrok, who has been very good for the Leafs this season, and expect to add to the bottom 6 players mid season knowing they had 2 holes to fill.
 

Beloved by his teammates and trusted by his head coach, Toronto’s ultimate utility forward Alexander Kerfoot has jumped from lines one through four and skated in all three positions up front throughout his four-year run since 2019’s infamous Nazem Kadri blockbuster.

At various points in his Leafs tenure, Kerfoot has been at risk of being moved, largely because his $3.5-million cap hit has complicated matters for a contender so intent on maximizing every penny on the budget.

Many stories get written about what it’s like to get traded. Kerfoot’s story is about what it feels like to avoid a trade.

The 28-year-old is in the final months of an expiring contract, and unless he’s willing to re-sign for a significant discount, his Leafs days are likely numbered.

Faced with a decision to ship out Kerfoot or keep him as an “own rental,” GM Kyle Dubas spent draft capital to do the latter.

When acquiring Ryan O’Reilly and Noel Acciari from the St. Louis Blues, Dubas could have balanced Toronto’s books by moving Kerfoot to Missouri, according to Elliotte Friedman’s reporting.

Instead, Dubas paid the Minnesota Wild a 2025 fourth-round pick to retain 50 per cent of O’Reilly’s salary and keep Kerfoot safe from six weeks of meaningless hockey.
 
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2. Ryan O’Reilly

Age on July 1: 32
Position: Centre
2022-23 salary cap hit: $7.5 million


The latest: The St. Louis Blues prioritized locking up the next wave of Blues forwards (Jordan Kyrou, Robert Thomas) over its veterans during the summer of 2022, and O’Reilly agreed to set extension talks aside until midseason.

By then, it became apparent GM Doug Armstrong — who knows a contender when he sees it — would be selling.

O’Reilly (and Noel Acciari) helped Armstrong recoup useful draft picks, while the forwards felt rejuvenated by a high spot in the playoff race and the potential for a Stanley Cup run.

Toronto Maple Leafs general manager Kyle Dubas, who’s in a contract year himself, did not discuss an extension with any of his rental acquisitions.

The Leafs’ focus is entirely on the present. Contract decisions depend on what happens on the ice.


O’Reilly suffered a broken finger in just his eighth game with the Leafs but is expected to be ready for action before the postseason begins.

.....................

The team and the Ontario returnee have sparked a quick, mutual love.

With Horvat and Larkin signing midseason, O’Reilly may be the most coveted UFA centre this summer — and the Blues have not closed the door on a return to his championship home.

As one of the game’s premier two-way centres, the Selke-winning O’Reilly could point to Nazem Kadri’s $7-million AAV in Calgary as a comparable.

But would he be willing to take a little less to remain a Maple Leaf?
 

2. Ryan O’Reilly

Age on July 1: 32
Position: Centre
2022-23 salary cap hit: $7.5 million


The latest: The St. Louis Blues prioritized locking up the next wave of Blues forwards (Jordan Kyrou, Robert Thomas) over its veterans during the summer of 2022, and O’Reilly agreed to set extension talks aside until midseason.

By then, it became apparent GM Doug Armstrong — who knows a contender when he sees it — would be selling.

O’Reilly (and Noel Acciari) helped Armstrong recoup useful draft picks, while the forwards felt rejuvenated by a high spot in the playoff race and the potential for a Stanley Cup run.

Toronto Maple Leafs general manager Kyle Dubas, who’s in a contract year himself, did not discuss an extension with any of his rental acquisitions.

The Leafs’ focus is entirely on the present. Contract decisions depend on what happens on the ice.


O’Reilly suffered a broken finger in just his eighth game with the Leafs but is expected to be ready for action before the postseason begins.

.....................

The team and the Ontario returnee have sparked a quick, mutual love.

With Horvat and Larkin signing midseason, O’Reilly may be the most coveted UFA centre this summer — and the Blues have not closed the door on a return to his championship home.

As one of the game’s premier two-way centres, the Selke-winning O’Reilly could point to Nazem Kadri’s $7-million AAV in Calgary as a comparable.

But would he be willing to take a little less to remain a Maple Leaf?
I realize that O'Rielly is a UFA and former cup and conn Smythe winner but I really don't see how he can command 7M in a year where he was really declining and on pace for 41 pts. Not comparable to Kadri's career year at all.

I can't see him getting any more than 5.5M
 

1. We’ve reached the stage where the actual hockey will rightfully seize centre stage.

Still, lurking in the shadows of the Toronto Maple Leafs’ playoff experience — and, presumably, the minds of their many players and staff members with uncertain futures — will be what happens when the hockey is over, for good or sad.

Ryan O’Reilly — the grand deadline swing and passionate breath of wisdom on the Leafs’ bench — is doubling as both Toronto’s latest difference-maker and one of the NHL’s most compelling UFAs-to-be.

So many factors come into play when an in-demand player can select his own landing spot: a chance to win, long-term security, and money of course.

But when it comes to an emotional and familial connection, the Maple Leafs should have a leg up on some of the Ontario native's other options this summer.

Another factor that could sway him to stay, with the franchise that paid a handsome sum to rent him for one run, is culture.


Since his arrival, the exacting O’Reilly has been speaking glowingly about the level of detail in Leafland, be it from coaches in meetings, teammates offering opinions, or the development staff that helped him stay in shape and rehab from his finger surgery.

“It’s impressive,” says O’Reilly, now on his fourth NHL stop.

“I always knew there was lots of staff here and resources. Getting here and seeing it firsthand, it’s at first a little overwhelming. Once you kind of get a handle and get to know everyone, it’s pretty amazing, the help that you have to assist your play,” O’Reilly raves.

“Like myself coming back from injury and just every facet of your meals to… everything. It's just so elite and above everything I’ve seen before.”

At the risk of putting the cart before the horse, I ask O’Reilly if all these extras — doctors, development staff, nutritionists, resources — can make a difference when it comes time for him to sign a new contract.

“Yeah,” he replies, without skipping a beat. “Obviously, yeah, that's for sure. We got playoffs still to come, but, yeah, there’s not a bad thing I can say for this organization. They do everything the right way.”

“And if something doesn't work here, they’re changing, right? They’re always looking at ways to get better. And that's the reason why it is such an amazing franchise.”
 
Re-sign him. No excuses.
They'd be crazy not to.

Bury/buy out guys until you can make it happen. We're a completely different group with him in there. And my opinion will be the same even if we lose the series.

O'Reilly has come out and said how he has been blown away at how great the Leafs organization is, the resources they have. Add the fact that I'm pretty sure his wife is from Scarborough, and his parents live not too far from me, about 2.5 hrs west of Toronto, I'd find it very hard to believe he isn't coming back.
 
If ROR signs here it will NOT be about $$$ .. it will be where he thinks he can get another Cup ie Blues are dead .. my bet if we get through a round or two then he resigns here .. if we win a Cup then it is a jump ball but I would still bet he signs here
 
When did Pillar start playing hockey?

IMG_2937.jpeg
 

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