Insider says Ryan O’Reilly won’t re-sign with Maple Leafs

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. 

When Ryan O’Reilly Hit the Ice in Toronto, He Fit 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. 

At least from one hockey insider suggests O’Reilly will be moving on and speculates on 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 will 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 again.

The "Jeff Marek Show" recently discussed the future of UFA Ryan O’Reilly and 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.

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. 

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 skill set 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.