Weekend FTB: Raddysh is nice, now what?

If you missed it late yesterday the details of the Darren Raddysh deal are now known:

Raddysh 8 year $8.5M Cap Hit Deal:

Year 1 $1M Base & $10M Signing Bonus
Year 2 5M & 6M SB
Year 3 4.5M & 6M SB
Year 4 4.25M & 4M SB
Year 5 3.45M & 4M SB
Year 6/7/8 3.3M & 3.3M SB

No Move throughout, 16 team No Trade Years 7/8

Rep'd by Craig Oster @TheHockeyAgency…
— PuckPedia (@PuckPedia) June 19, 2026

Darren Raddysh: Been Toronto Down 🦖@Raptors pic.twitter.com/28EO5WAEmE
— Toronto Maple Leafs (@MapleLeafs) June 19, 2026

John Chayka mentions that he was interested in Raddysh back when he was in junior playing with then Coyotes prospect Dylan Strome. He tried to sign him out of junior, but Raddysh (undrafted) signed an AHL contract and eventually ended up in Tampa.

He calls the move aggressive and admits it's not without risk. He also calls this move an organizational win.

Terry Koshan asks outright about Matthew Knies. Chayka goes back to his opening press conference comments about it being his job to evaluate everyone. But he downplays the idea that they can improve the roster by trading a good young player. He says it "makes for good writing" and is something that interests people. He calls the idea not probable.

On Ben Danford, Chayka had a lot of praise, but sounded a note of caution that this will be a process and they have a lot of options on the right side right now.

The whole presser is worth a listen. His answers are very "designed for PPP" in a sense. When asked about Raddysh and the PP, he talks up his five-on-five game. He is himself, that's for sure, and he's not going to put on the mantle of a standard NHL GM and talk about the game the way the TV men do. Listen to him deal with the question about the Leafs "handing out NMCs". Unlike me he didn't sarcastically say "like candy".

About Matt Knies – remember that the rule at this time of the year is that GMs lie. And Chayka himself discussed that very idea in answer to a question about their stealthy deals. He said things about being forthright with the fans at the right time. So when he says about Knies that he's evaluating, but trading a player like him won't make you better... well... okay.

This reporting and speculation started below the surface long before Nick Kypreos came up with a fully fleshed out theory of how a trade could work for the Leafs. And Kypreos never pretended he wasn't just advancing a theory. But since then several other reporters have stated plainly that conversations are happening between other teams and the Leafs.

This is Chris Johnston on the topic (from before the Chayka presser):

Johnston describes the past on this file a little differently to how it often is told. He describes the Leafs under Treliving as actively shopping Knies last spring. And that three or four teams got somewhere down the road towards a deal but that it didn't happen.

We've all heard the stories about Montréal and gossip about Kent Hughes being angry and the trade being filed late. This has all become truthy now, but it's unlikely anyone who was there is going to speak on the record.

As for now, Johnston says the Leafs are "at least keeping their ears open to the possibility that Matthew Knies could bring them back multiple pieces." He also refers to what the Leafs are doing as a "refresh or retool" and that's a good way of looking at it. Step out of the dichotomy of contending or losing on purpose, and see that there is a lot of unexamined middle there.

Johnston then lays out why Knies' name is out there. He is under contract for term with no trade protection. He says that what the Leafs are doing is conducting an auction because they can trade him to any of 31 teams.

This all makes sense. Now if you've never bought anything at an auction – I have way too many times – you need to know that a seller can put a reserve price on something. And that's also clearly what's going on here, the reserve price on Knies is very high. The other thing about auctions is that when someone outbids you, the urge to win is really powerful and it takes a strong will to resist.

Someone might (improbably or not) best that reserve price.

This is not "shopping the player" or wanting to trade him for a specific return, but a willingness to be wowed by a return that can help now and in the future on multiple fronts.