Could the Leafs be eyeing a 3-time Stanley Cup winner in free agency?

The Leafs' decisions at center are likely hinging on whether or not they are able to bring veteran Ryan O'Reilly back this summer. I'm sure that the Leafs would love to have him back if he's open to the idea, but if he does indeed depart on July 1st, there's another veteran center who can provide a wealth of experience and a winning pedigree to the Leafs' locker room. It would be a risky acquisition though.

With former Chicago Blackhawks captain Jonathan Toews on an expiring deal and having already been informed by the Hawks that they would not be bringing him back, retirement is certainly an option for Toews. He has made a lot of money over the course of his career and he has won 3 Stanley Cups as well. Would he fit what the Leafs are looking for? It's hard to imagine that he wouldn't - even if he is 35 years of age.

Toews was long referred to as "captain clutch", during his hay day with the Hawks. He won the Conn Smythe Trophy in 2010, scoring 29 points in 22 games and hoisting his first career Stanley Cup. Obviously, a lot of time has passed between then and now, but there are certainly lessons he can teach to a number of the younger Leafs and after scoring 31 points in 53 games last season, he proved that he can still hang.

A deal for Toews wouldn't come without its risks. His struggles with CIRS have been well-documented and he has missed significant time over the past few years because of it, including a full missed season in 2020-21. However, with the Leafs having such a great medical staff under their employ, it's tough to argue that Toews wouldn't have top tier care and that the Leafs would help him manage his illness with their seemingly endless resources.

The main question here is; would Toews even consider playing in Toronto? After playing his whole career to this point with an original six team, we know Toews can handle the pressure of a volatile market. However, as a Winnipeg, Manitoba native, there is at least some belief that he wouldn't mind playing closer to home.

We know that the Leafs, in the past, have valued bringing in some of these veteran guys to help guide their young core in the right direction. However, now that the core in Toronto is older, Toews' role may be more suited to helping them find that next gear, rather than mentoring them. It's really anyone's guess if he would consider a deal in Toronto - especially given the Leafs' current cap constraints. If Toews did agree to a deal in Toronto, it would likely be a very short-term deal and at a cap hit very close to the league minimum.

Time will tell if there's any appetite for a Toews/Leafs partnership here, but it's certainly fun to think about.