It feels like talking about Morgan Rielly trades is like beating a dead horse. The topic has been so widely covered that there doesn’t seem to be really anything left to say.
Interestingly, insider Jeff Marek made a comment on the matter, pointing towards an opportunity that the Maple Leafs had to trade Rielly years ago, and blew it.
During a recent appearance on Toronto Sports Rush, Marek referenced the juncture in which the San Jose Sharks were looking to trade Erik Karlsson. At that time, the Leafs were considered one of the most interested parties in making the deal happen.
As we all know, the Pittsburgh Penguins stepped up and grabbed Karlsson, and pretty much all of his substantial cap hit.
The Leafs, meanwhile, came away with nothing. As Marek noted, the Karlsson-for-Rielly deal (plus other pieces, presumably) wasn’t about the Leafs putting together a package that made sense. It was about the retention that Toronto wanted from San Jose.
“For a while there I think we all thought there was gonna be something between San Jose and Toronto around Erik Karlsson, and Rielly would've been part of it; retention I believe was a major issue there.”
The Penguins got Karlsson at $10 million against the cap, with the Sharks retaining $1.5 million.
That’s something the Leafs could have done but didn’t. So, it begs the question, why?
Rielly missed trade another part of Brad Treliving’s Maple Leafs legacy
The Penguins-Sharks trade happened in August 2023. Karlsson was coming off a 100-point season, with his value higher than ever.
Former Leafs GM Kyle Dubas wasn’t afraid to figure out a way to make the cap hit work. Another former Leafs GM, Brad Treliving, was too shy to pull off the deal.
Rielly and his cap hit remain in Toronto, while Karlsson moved on to Pittsburgh. In all fairness, Karlsson hasn’t been the same player since leaving San Jose. But had the deal happened, we wouldn’t be having the endless conversations about trading Rielly. The deal would have settled the matter, at least as it pertained to Rielly.
In August 2026, it seems that Karlsson is once again available. And the Leafs are still looking to move Rielly. It might just be that a Karlsson-for-Rielly trade could finally happen. If the numbers work out, there’s no doubt that John Chayka won’t hesitate the way Treliving did.
If it makes sense for the Leafs, we may see a late-summer stunner still.
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