Ryan O'Reilly has established himself as one of the best leaders in the NHL. That standard was confirmed during the 2019 Stanley Cup playoffs, when he led the St. Louis Blues to the only Stanley Cup title they have won in their team history.

O'Reilly scored the opening goal in their 7th game triumph on the road over the Boston Bruins with a deft deflection that allowed a point shot from Jay Bouwmeester to slip past Boston goaltender Tuukka Rask. The Blues never looked back after that and earned a 4-1 triumph. A couple of hours after that O'Reilly goal, he lifted the Stanley Cup in Boston.

The Blues had a miserable 2022-23 season, and with O'Reilly looking at free agency in the offseason, the team decided to move O'Reilly to the Toronto Maple Leafs. No team has had more difficulty in its recent playoff appearances than the Maple Leafs, and adding O'Reilly seemed to be just what Toronto needed.

The Toronto experience

The Leafs finally earned the first-round victory when they dispatched the Tampa Bay Lightning, but their playoff season came to an end the next round when they fell in 5 games to the Florida Panthers.

The 32-year-old will be a free agent July 1, and O'Reilly should have options open to him. However, he knows the joy of playing with a Stanley Cup winner, and his best options may be with teams have realistic chances of at at least contending for another Cup crown.

The belief here is that he should not return to the Leafs, even though there have been rumors that they are interested in bringing him back.

If he wanted to return to Toronto, it seems quite likely that he would have to accept a deal that would pay him less than $5 million per year. Since he has had cap hits of $7.5 million in each of the last 7 seasons, he could probably do better elsewhere.

Back from where he came

The Blues had an awful season as they finished in 6th place in the Central Division and out of the playoffs.

They were never able to turn their season in a positive direction, but that doesn't mean that the Blues won't be able to return to the playoffs in the upcoming season.

They have had success with a similar cast in the past, and head coach Craig Berube is a strong leader. With just a bit more goaltending than they received last season, the Blues can return to the playoffs and possibly make an impressive run.

Most free agents who are traded in the late stages of their walk season do not return to their old teams. But O'Reilly has never had anything but good things to stay about the Blues and St. Louis, and he is still a good fit for a No. 2 center.

If the Blues were willing to offer him a contract in the $5-6 million range per season, it might be enough to get him back to that organization.

O'Reilly appears to be the best fit of any of the veteran free agent centers for the Blues, and he is likely to give his old team strong consideration

A solid fit for the Avs

Colorado was not able to put together the same kind of run in 2023 than they did in 2022 when they won the Stanley Cup in impressive fashion.

During the Avs' Stanley Cup run, they won 16 of their 20 Stanley Cup playoff games. They only teams to push them were the Blues and Tampa Bay Lightning, as each of those teams won 2 games in the series.

Why were the Blues able to push the Avs? Largely because of the leadership of O'Reilly. He scored 2 goals and 2 assists in the first 3 games of the series, providing his team with a road map of how to compete with the explosive Avs.

O'Reilly could provide the Avs with the kind of resourcefulness and know-how to succeed in the playoffs. Since Gabriel Landeskog's status is still in the air, O'Reilly might be the best fit for a team that wants to return to Stanley Cup glory.

Conclusion

O'Reilly has the track record of playing his best when the money is on the table. He excels at winning faceoffs, making plays in the clutch and helping his teammates perform their best in the most challenging situations.

Ryan O'Reilly is no longer at his physical peak, but his dynamic leadership skills will make him a great fit for any team that signs him. He would pay the biggest dividend for the Avs.