It is reasonable to assume that whenever a former Conn Smythe Trophy winner hits the open market, a bidding war for their services should ensue. That could once again be true in the case of upcoming free agent Ryan O’Reilly. The 2019 recipient of the aforementioned playoff MVP award was dealt from the St. Louis Blues back in february to his hometown team, the Toronto Maple Leafs. It was a tumultuous season for the 32-year-old, as he dealt with a broken foot prior to the trade and a broken finger in the lead-up to the playoffs. In total, O’Reilly missed 29 games due to injury and only managed to record 16 goals and 30 points during the regular season, his lowest marks in each category since the 2012-13 lockout shortened season.

While O’Reilly’s offensive output appeared to vanish out of thin air, there are caveats worth pointing out. Once he arrived in Toronto, O’Reilly piled up 4 goals and 11 points in 13 regular season contests. He then added another 3 goals and 9 points in 11 postseason games. In the playoffs specifically, O’Reilly provide not just steady, but timely production. He also averaged 19:49 time-on-ice (TOI) which ranked third among Toronto forwards behind only Mitch Marner (24:08) and Auston Matthews (22:52).

The veteran centre is coming off a contract originally signed with the Buffalo Sabres which paid him $7.5 million annually for 7 seasons. O’Reilly’s next contract is expected to feature a lower cap-hit on medium term, some contract comparables include Joe Pavelski ($7 million x 3 years in 2019), Claude Giroux ($6.5 million x 3 years in 2022), and Ondrej Palat ($6 million x 5 years in 2022). A fair contract projection for O’Reilly would be something in the $6 million range for 3 to 5 years. He should be viewed as an attractive commodity for several contending teams looking to bolster their center depth.

“It’s more than just a game here. It’s something really above and beyond.”

Ryan O’Reilly discusses being traded to Toronto and what it meant don the Maple Leafs jersey #LeafsForever pic.twitter.com/9HGNlld6Iu

— OverDrive (@OverDrive1050) June 7, 2023

Toronto Maple Leafs

O’Reilly’s brief tenure as a Maple Leaf saw him start at second-line centre allowing John Tavares to shift over to left wing. However, come playoff time O’Reilly found himself centering a third-line featuring rookie Matthews Knies and former Blues teammate Noel Acciari. O’Reilly’s versatility is part of the appeal for any team vying for his services, and Maple Leafs fans came to appreciate that aspect of his game rather quickly. Extending his stay in Toronto would likely require O’Reilly to take a hometown discount, considering the long-term extensions that loom large for Maple Leafs forwards Auston Matthews and William Nylander.

Pittsburgh Penguins

Kyle Dubas traded for Ryan O’Reilly less than 4 months ago, so would it really be a shock if the new President of Hockey Operations found a way to make O’Reilly a Penguin this July? Dubas spoke about wanting to improve the top-six in Pittsburgh this summer, and O’Reilly fits the timeline of a nucleus that includes Sidney Crosby, Evgeni Malkin and Kris Letang. The Penguins have just over $20 million in cap space to work with, allowing them to sign O’Reilly while also addressing the vacancies left by free agents such as forward Jason Zucker and goalie Tristan Jarry.

Detroit Red Wings

Red Wings General Manager Steve Yzerman is no stranger to acquiring former Blues, look no further than forwards David Perron, Robby Fabbri, defenceman Jake Walman and netminder Ville Husso. It’s worth noting that Detroit attempted to address the centre position last summer by signing Andrew Copp to a 5 year deal but the Michigan native is perhaps better suited as a winger or third-line checking center opposed to being a second-line mainstay. O’Reilly would provide great insulation for captain Dylan Larkin, allowing the first-line to feast on opposing depth. Yzerman and the Red Wings have an impressive $30 million in cap space, allowing them to be flexible and creative this offseason. There are reports of Detroit’s interest in Senators winger Alex DeBrincat, who is available through trade. Acquiring both O’Reilly and DeBrincat could bring the Red Wings contention window into immediate focus.