On HNIC, Elliotte Friedman provided a few nuggets on deals that were discussed but didn’t come to fruition at the 2023 trade deadline, including reports of interest from the Maple Leafs in both Mattias Ekholm and Erik Karlsson.

Signed for a $6.25 million AAV, the 32-year-old Ekholm ended up moving to Edmonton in a trade with only $250k in cap retention for the next three years, which would’ve been a tough deal to make work for the Leafs under their cap constraints (and willing third-party brokers for double retentions become much more difficult to find and are more expensive to incentivize on longer-term deals).

In San Jose, Erik Karlsson is enjoying a career resurgence with a Norris Trophy-calibre season with 80 points in 63 games, but he didn’t end up moving due to the complex nature of moving an $11.5 million AAV contract midseason. Based on the quotes coming out of Karlsson after the Timo Meier deal, he doesn’t sound like a player who is content to stay put in San Jose through a rebuild at this stage in his career.

Erik Karlsson: “When you trade a guy like Timo, I don’t think that shows that this is going to be a quick turnaround. It’s unfortunate, but I understand it. I’ve been around the game long enough to understand what needs to be done from an organizational perspective, and it just sucks that it happened to be where I’m at in this stage of my career.

I want to win. When you’re younger, you think you have all the time in the world, you don’t realize how fast time goes.”

As their main addition to the blue line, the Leafs ended up acquiring a much different type of defenseman than Karlsson in Jake McCabe, but they did also add pending UFA Erik Gustafsson from Washington. Gustafsson is a top-15 point-producing defenseman in the league this season and is a power-play specialist, albeit he is limited to secondary man-advantage minutes in Toronto due to Morgan Rielly’s presence on the top unit.

The fact that management identified this as a need and didn’t want to subtract Rasmus Sandin’s skill set— he played the point on the second power play and has some offensive upside at five-on-five as well — without returning a player who could provide value in those areas is noteworthy.

If the Leafs will revisit this in the offseason remains to be seen, but it was interesting to hear Kyle Dubas cite the fact that they kept Boston’s first-round pick acquired in the Washington trade (rather than flipping it for more immediate help) because it either gives them the opportunity to add a higher-end prospect at the draft or allows them to be more seriously involved in the trade market in June.

While new addition Jake McCabe is under contract for two more seasons, it still seems likely the Leafs will remain quite active in the defense market this summer. With Justin Holl not signed beyond the season, the Leafs currently only have one right-handed NHL defenseman under contract for 2023-24, Timothy Liljegren.

Rasmus Sandin is now a member of the Washington Capitals. This offseason, Mark Giordano will be entering the final year of his contract at age 40, and TJ Brodie will be entering the final year of his deal at age 33. Jake Muzzin is signed for one more season, but his ability to continue an NHL career with his cervical spine injury is in serious doubt.

In the system, promising Finnish defense prospect Topi Niemelä could cross the pond and join the Leafs organization (likely with the AHL Marlies to start), but there are no blue-chippers ready to make the jump as soon as next Fall.

That said, while it helps that the cap ceiling isn’t in place for the offseason, the complicated nature of making a trade work on a contract this big in AAV and duration will not necessarily be significantly easier. Whether the Leafs should be pursuing a contract with four years left on it for a 33-year-old Karlsson is definitely debatable. With new contract negotiations upcoming with William Nylander and Auston Matthews as soon as July 1, only in a scenario where significant retention is in place would it seem to make any modicum of sense, which would require San Jose — and any third-party broker if relevant — to retain on Karlsson’s cap hit all the way through the 2026-27 season.