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Insider Says Ryan O’Reilly Won’t Re-sign with Maple Leafs

Ryan O’Reilly was a solid rental for the Toronto Maple Leafs. However, he won’t resign with the team. Why not? Where might he land?

On Monday, the Toronto Maple Leafs held their exit interviews. A number of players spoke with the media and were asked questions about how they felt about staying with the organization. 

For what it’s worth, both Auston Matthews and Mitch Marner answered in the affirmative. They want to stay in Toronto. This is where they want to play. They “love” their teammates and want to keep the group together. 

One player who was interviewed wasn’t – at least in my hearing – asked if he wanted to stay with the Maple Leafs. That player was Ryan O’Reilly. 

Related: Assessing Keefe’s Tenure as Maple Leafs’ Head Coach

When Ryan O’Reilly Hit the Ice in Toronto, He Fitted In Quickly

From everything I’ve seen, Ryan O’Reilly is a class act. He fits in easily; he makes himself part of the group; he’s almost like a second coach on the bench. He talks – lots, from what I read. And other players listen. 

But there seems no sense that he will stay with the Maple Leafs. He was a rental only. With his contract ready to expire, it seems he will be skating away into the sunset. 

In this post, I will share the news – at least from one hockey insider – that suggests O’Reilly will be moving on and where he might land. What factors could influence his decision?

O’Reilly Was a Solid Rental Option, But He Likely Won’t Return to St. Louis

During the 2022-23 season, at the trade deadline, O’Reilly became a rental player for the Maple Leafs. St. Louis parted ways with the former Conn Smythe winner because they were not going to make the postseason and they had taken this opportunity to trade away expiring contracts as a way to focus on bringing younger talent onto the roster. 

Two of these key acquisitions, former Maple Leafs’ forward Kasperi Kapanen and former Detroit Red Wings player Jacob Vrana, significantly changed the landscape, making it less likely that O’Reilly to return to St. Louis. These new additions have combined salaries high enough to limit any financial room for O’Reilly to pull on a Blues’ jersey.

In the video below, Jeff Marek Show discusses the future of UFA Ryan O’Reilly. He discusses whether it would be possible for the Maple Leafs to fit him within their cap. If not, where else might O’Reilly land?

Toronto’s Salary Cap Constraints Are Prohibitive

O’Reilly is now 32 years old and he’s on an expiring contract. He has a high hockey IQ; and, given his resume, he’ll be attractive for another organization looking for experienced leadership and secondary scoring. It’s likely that this next contract will be O’Reilly’s last big one.

That puts him out of touch with Toronto’s salary cap situation. O’Reilly will be looking for a team that has salary cap space enough to pay him the larger contract he desires. Who might that be?

For sure, as Marek notes, it won’t be the Maple Leafs. O’Reilly’s contract ask is above what the Maple Leafs can pay. While he would be an excellent fit on the Maple Leafs’ roster, financial constraints won’t allow the Maple Leafs to clean off a landing spot for the skilled forward.

Related: What 3 Steps Should the Maple Leafs Take Next to Fix The Team?

So, for Those Who Care, Where Might O’Reilly Find a Landing Spot? 

Because O’Reilly won’t re-sign with the Blues or find a suitable agreement with the Maple Leafs, other teams could emerge as potential destinations. For example, for Marek, the New York Islanders are always close to the playoff picture and might desire to bolster their roster. O’Reilly could be an appealing addition to their lineup. 

Ryan O'Reilly Maple Leafs injury
Ryan O’Reilly was a good addition for the Maple Leafs

However, Marek notes that the Chicago Blackhawks might also be a factor. The Blackhawks’ fortunes changed dramatically with their draft lottery win and the upcoming acquisition of top prospect Connor Bedard. Surrounding Bedard with experienced veterans like O’Reilly would be crucial. And, O’Reilly’s professionalism and skillset could make him an ideal candidate in Chicago. 

Although questions remain about O’Reilly’s contract and its length and numbers, suddenly fitting in with the Blackhawks makes sense.

The Bottom Line

Although Ryan O’Reilly was a great addition to the Maple Leafs’ roster, he’ll likely move somewhere else as a free agent. Obviously, a lot of fans – including myself – would love to see him take a team-friendly contract and sign here. However, he isn’t at Mark Giordano’s final go-round in his career.

Thus,  the possibility of him re-signing with the Maple Leafs slams into the team’s salary cap limitations.

Of the other potential destinations, the Chicago Blackhawks seem to be a leading candidate – at least logically. For those who have become O’Reilly fans, it will be fascinating to see where he chooses to play and who might offer him the best contract.

Related: The Frustrations of Maple Leafs’ Fans: What Do They Say?



  1. Jon Harding

    May 16, 2023 at 1:43 am

    I’ve never seen a more chaotic ending to a Maple Leafs season. Zero accountability. Everyone acting as if they were indeed good enough to have won the Cup had it not been for a few bad breaks. Shanahan assumably going to ride in and restore order in a day or two after he collects his thoughts. Rubbish. They lost. They weren’t good enough. The team has a million flaws and the GM’s approach was flawed. A city and team swept up in delusion.

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  3. Roy Peters

    May 16, 2023 at 2:07 pm

    The problem with Marek and all the talking heads, they don’t know anything about how a person thinks and what he wants in the future. The money to someone who has made millions is not necessarily the most important thing. The most important can be winning a cup with his favorite chidhood team.

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