Toronto Maple Leafs forward Ryan O’Reilly is a pending unrestricted free agent, who is very likely heading to the open market on July 1. O’Reilly would be wise to hold off on signing a contract extension until free agency begins. Besides Jonathan Toews, the Leafs center is head and shoulders above the rest of the free agents available to help down the middle.
O’Reilly enjoyed his time immensely as a Maple Leaf, and while there’s still a very outside chance he agrees to a new deal with Toronto’s general manager (GM) Brad Treliving, I’d expect to see the former Conn Smythe trophy winner sign with one of these three teams this summer:
Colorado Avalanche
With Gabriel Landeskog out for next season, the Colorado Avalanche are in need of some help up front, and specifically in the number two center hole. O’Reilly fits in perfectly and there’s certainly a chance of a reunion this summer.
O’Reilly was originally drafted in the second round by the Avalanche back in 2009, and now at 32 years old, could find himself back in mile high. Full circle indeed; he spent six seasons with the franchise from 2009-15 before being dealt to the Buffalo Sabres in a summer blockbuster.
This offseason, Colorado has some money to spend and are going to check in on O’Reilly’s price tag. While he won’t be pulling in $7.5 million per season anymore, I’d expect to see something north of $6 million as an average annual value. "The Factor" impacts the game in so many ways, and you can’t always check a score sheet to find the evidence.
At this point, I see the Avalanche as the favorite to land the veteran center.
St Louis Blues
He’d have to take quite the pay cut or "old-team discount" if you will, but if O’Reilly wants to return to the St Louis Blues, it does feel like there’s still room. The amount of mutual respect between the organization and player is unmatched. Blues GM Doug Armstrong kept O’Reilly very informed throughout the trade process which landed him in Toronto. Because of the strength of this relationship, I could see St Louis being very much considered.
Armstrong doesn’t have a ton of cap space to work with, so the contract will have to be creative. The Blues are also trying to trade a defenseman, according to hockey insider Frank Seravalli, so this could help free up some more cap space to comfortable fit O’Reilly back in.
While in Toronto, O’Reilly wasn’t happy with the amount of chances he was creating and felt his offensive game wasn’t on full display. Defensively, he was solid as ever, but yes, he was inconsistent at times. Overall, the 2022-23 season was a grind for the veteran forward. He dealt with a slow start offensively, some bad breaks on the injury front and inconsistent production throughout the season. One to forget, no doubt, but don’t bet against him. O’Reilly will bounce back and expect to see him hover around the 55-point mark in 2023-24.
St Louis is retooling on the fly and they are trying to stay competitive while also getting a bit younger and more versatile. If the Blues have a chance to bring back their old captain, it may be a wise move.
Pittsburgh Penguins
I consider the Pittsburgh Penguins a wild card in the O’Reilly sweepstakes based on a couple of things. I don’t believe he’s a fan of head coach Mike Babcock, so even though the fit with the Columbus Blue Jackets could have made sense, I don’t see it happening. Enter Kyle Dubas and the Penguins, which have a gaping hole at their third-line center position.
O’Reilly and Dubas had a great relationship while together with the Maple Leafs, and depending on the sales pitch, there’s some potential. Pittsburgh has some money to spend but will prioritize their crease first. Starting goaltender Tristan Jarry is a pending free agent, and Dubas has begun evaluating his game to decide whether or not to re-sign Jarry or move on. Once this order of business is complete, the focus will shift up front.
The only thing working against O’Reilly is his footspeed, as the Penguins are prioritizing increasing team speed this summer. Depending who they are able to land to play wing among their bottom six, could have a huge impact on their interest in bringing in O’Reilly. The Dubas/Penguins dynamic is something to watch for though, as I do see some ex-Maple Leafs heading down to Pittsburgh to join forces with their old GM.
The O’Reilly sweepstakes are going to be fun to watch as "The Factor" — or "Snooks" to some — has a big decision to make this summer. He’s not getting any younger, and this may be his last chance to land a lucrative multi-year contract. To me, Colorado makes a ton of sense. Regardless of where he winds up, it sounds like a reunion of sorts is coming his way.
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