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Originally Posted by You Need a Thneed
Nope, that clause is one of the things that changed in the 2020 CBA extension.
No longer does a player have to have been on the reserve list for the most recent trade deadline.
Or else Seth Jones wouldn’t have been able to (future) sign an 8 year extension before next years trade deadline.
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Hmm it looks like the trade deadline reserve list thing is somewhat different for players still under contract, but in the case of an about to expire contract like Hyman, only Toronto can sign him to an 8 year deal.
From that same article:
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This means that if the Maple Leafs were to trade Morgan Rielly to any team at any time between now and the next trade deadline, the acquiring team could sign him to an eight-year extension right away. The Leafs can, of course, also extend Rielly now for eight-years.
The only way around this requirement that a player getting an eight-year extension cannot be an expired UFA, and they must have been on the signing team at the prior trade deadline (or signed through to the next one) is a sign and trade. The Maple Leafs could sign a valid SPC with Hyman today for eight-years and then make the trade to the team that wanted that deal done. To the best of anyone’s recollection, this has never happened in the NHL.
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It's why the reports are specifically of there needing to be a "sign and trade" to facilitate an 8 year deal with Edmonton:
https://twitter.com/user/status/1418196333782093833
If he reaches free agency, he can only sign 7 years.