Toronto had a chance to trade Morgan Rielly for Erik Karlsson three years ago but Toronto's desire for heavy salary retention got in the way of finalizing a deal.
Jeff Marek recently discussed the Morgan Rielly trade rumours and revealed that the team could have actually had ideal in place three years prior that would have sent him to the San Jose Sharks in exchange for star defender Erik Karlsson.
Morgan Rielly was easiest to trade when Toronto needed him most
However Marek stated that the reason the deal never went down was because Toronto wanted heavy retention on Karlsson's then-$11.5M contract:
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.
Karlsson ended up going to Pittsburgh while San Jose did retain $1.5M of his salary leading to the Penguins only taking on a $10M cap hit.
Marek did not specify how much retention Toronto wanted. What is known is that San Jose ultimately retained $1.5 million annually when Karlsson was traded to Pittsburgh, leaving the Penguins with a $10-million cap hit.
At the time, Rielly was 28 and still firmly in his prime, but he was coming off an uneven 2022-23 regular season with 39 points in 65 games before producing 12 points in 11 playoff games. That postseason surge helped reinforce his value at a moment when Toronto still viewed him as a central piece of the blue line.
Toronto was banking on Rielly keeping that production or even improving on it, but instead he declined and has now become someone who is a lot harder to deal away. There was a potential San Jose deal this season but they pursed Darnell Nurse instead.
Toronto replaced Rielly after his trade leverage weakened
With Rielly unable to reach those heights he once hit in 2022 and showing a steady decline, the Maple Leafs decided they needed to make a change. Darren Raddysh came in after a 70-point breakout campaign and the team is hoping he can build off that.
He adds a dynamic that Rielly doesn't which is a blazing fast and hard shot, and is able to find himself adding a bit more physicality than Rielly could. That means Rielly is arguably the most expendable he's ever been however there's little room to move him - he's worth $7.5M per season and holds a full no-movement clause.
He did submit a four-team list to the Maple Leafs this past summer but that doesn't guarantee he gets traded there or at all. It's more a list of destinations he would prefer to play if the team were to make a trade.
It also creates a potential cycle, because if Raddysh is unable to replicate his production or improve on it and become that star #1 defender Toronto needs, then they find themselves in a very similar situation to where they are now with Rielly. One good year followed up by regression combined with the same trade protection and even more expensive contract - it's nigh-impossible to move.
Toronto needed to keep Rielly three years ago because they were banking on him improving on an already stellar season and that he would play himself into that star defender after years of progress. Instead, they found themselves with a hard to move contract and their only real mistake - if you can call it that - is not having a hunch that Rielly's production wasn't sustainable long-term.
Should Morgan Rielly be kept or traded by the Maple Leafs?
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