Confirmed Trade: [TOR/TBL] Darren Raddysh (signs 8 years, $8.5M AAV) for 2026 5th round pick (MOD WARNING 253)

[Oleksiak]

Don't disagree on the risk of aging poorly, but there was never in a million years a way the Leaf's were signing DR to a 4 year deal. This is like the people saying "Don't like trade protection, just don't give it out!" ignoring the fact that situation would 100% guarantee that you're never getting a UFA to sign/extend with your team long term.

IMO - this was a gamble, and Chayka was left some pretty crappy cards from Treliving. This is doing the best he could with what he had. If this goes poorly, so did probably everything else and the Leafs are no worse off.

Comparison of a TERRIBLE deal would be to when Bowman was the Hawks MG and traded a boatload of assets to CLM for Seth Jones during a rebuild. Hawks essentially sent Boquist (recently drafted 8OA), 2021 12th OA, and their 2022 1st (ended up being 6OA) for Seth Jones (removed some extra picks which essentially cancelled out). That's a TERRIBLE deal for a rebuilding Hawks team which hampered the team going forward. If the Leafs melt down, IMO they are no worse off with this deal.

They are when they have to give up more assets to get rid of the contract.

 

[TheKrebsCycle]

Leaf fans should be at least concerned that Raddysh played much better with Moser than anyone else.

False . Played excellent away from him this season ( obviously excellent w ).

 

[Strangle]

Great signing. I'll worry about the year 2033...when its 2033 lmao

Until then, the Leafs just upgraded their team heavily

There are 3-4 different and very team friendly options to bury this contract

The leafs are using their financial muscle here and there are zero concerns about the back end of this contract.

Raddysh will get paid and also not count against the cap (or count very little) once that day comes

 

[sd1976]

What exactly was the point of the Philly trade?

Moving one of the 3 non waiver eligible goalies. Getting a needed puck mover and adding a pick plus 5 million in cap space. Thought that would be pretty obvious.

 

[Strangle]

At this point, unless they bring in at least one more big defenseman I don’t want to move reilly

If Reilly can play 3rd pairing and run PP2 that keeps his minutes in check and gives us a lot more depth on D.

Don’t dump Reilly unless you’re getting an actual hockey trade done

 

[Oleksiak]

Moving one of the 3 non waiver eligible goalies. Getting a needed puck mover and adding a pick plus 5 million in cap space. Thought that would be pretty obvious.

They didn't need yet another defenceman who can't play his position at the expense of one who can.

 

[stone fury]

Risky play for anyone who did this inevitable deal, but good for raddysh

 

[Jee]

Reading this thread

 

[GQS]

At this point, unless they bring in at least one more big defenseman I don’t want to move reilly

If Reilly can play 3rd pairing and run PP2 that keeps his minutes in check and gives us a lot more depth on D.

Don’t dump Reilly unless you’re getting an actual hockey trade done

Nawww move Rielly out ASAP. I like the guy as a person, but I really don't want to see him in a Leafs uniform again. Team needs at least a good facelift if they're not going to rebuild and moving Rielly out would change things significantly. Chayka won't do it unless Matthews wanted to leave, but I'd totally move him too and get a nice haul and turn the page on the Matthews era and start a new one.

 

[KniesMadeBradyCry]

They are when they have to give up more assets to get rid of the contract.

Why will they give up assess to get rid of it? They have cap space out the wazoo, and will be keeping him for the next few years regardless. His cap hit % in 4-5+ years will be so low that he will be easy to move if needed.

 

[sd1976]

Reilly and a 3rd is not "precious assets"

They are when you consider we got a better player at a lower cap hit and still have Rielly and that third. Even if they only get a 2nd for Rielly they are still way way ahead.

 

[KniesMadeBradyCry]

They didn't need yet another defenceman who can't play his position at the expense of one who can.

Who’s that? The metrics say you’re wrong. But you already knew that as soon as you started typing.

 

[Strangle]

Why will they give up assess to get rid of it? They have cap space out the wazoo, and will be keeping him for the next few years regardless. His cap hit % in 4-5+ years will be so low that he will be easy to move if needed.

It might actually be less than 3% by 2033

 

[um]

There are 3-4 different and very team friendly options to bury this contract

The leafs are using their financial muscle here and there are zero concerns about the back end of this contract.

Raddysh will get paid and also not count against the cap (or count very little) once that day comes

I think you’re a little optimistic that Raddysh will just go away at age 36/37.

And I do like the contract. But like many players, he’ll likely be overpaid in his last few years. It’s no big deal.

 

[WetcoastOrca]

The guy is one of us, he bleeds blue and white and he always has.

I just learned this today, but he has the passion and this team needs it

Sounds more like he bleeds green. That’s a hell of a lot of money for his first big contract.
And yes he’s one of you. Except for the $68 million he just got.

 

[Oleksiak]

Who’s that? The metrics say you’re wrong. But you already knew that as soon as you started typing.

Andrae. I don't care what some analytics dweeb with a spreadsheet comes up with, it's painfully obvious that his play in his own zone is not acceptable if you actually watch the game.

 

[SnuggaRUDE]

He's pretty good, how long will he stay that good is another question entirely.

 

[Donnie D]

Let's go down that path. Matthews when "healthy" is clearly playing hampered, Hiller completely bombs as a coach, and the Leaf's continue to be a train wreck. As a result, Leaf's end up at the bottom of the Atlantic and give a top 10 pick to BOS (or PHI). They then decide to rebuild, move short term assets at the TDL and move AM and WN summer of 2027 and rebuild around Knies, McKenna and whatever they get back. By moving AM then, he can sign a new deal with where he's traded so he probably has slightly more value than he does right now. WN's value doesn't go down with still have something like 5 years left on his deal. As a result, the Leafs are no worse off than if they decided to rebuild this summer. If they go down that path, the Leafs are doing a tear down rebuild and they're accepting 5+ years of pain and DR's contract isn't a hindrance from the team doing anything.

The only way this is a MAJOR mistake is if the Leafs are good, but Raddysh is terrible and his contract keeps the team from doing what is necessary to get over the top. I think that's unlikely, because Raddysh was a decent 2nd pair d-man before his career year, and I don't see a situation where everything goes well like AM is back to his old self, Hiller get the team playing well, goaltending is solid, and Raddysh is the only thing that holds the team back.

Quick Summary:
Positive view: Leafs bounce back and are at least a bubble team in the murder's row Atlantic. 1st rounder DP surrendered to PHI/BOS is somewhere between 14-19 and the team has at least a punchers chance.

Negative view: 2025-26 performance continues - and the Leafs have to blow it up. Raddysh contract doesn't hurt them at all in this situation.

Decent 2nd pair? No, he was a 6-7 defenseman who was scratched at the beginning of last season.

If it came down to just money he’d get $10M+ AAV on July 1st.

 

[Donnie D]

Decent

 

[KniesMadeBradyCry]

Andrae. I don't care what some analytics dweeb with a spreadsheet comes up with, it's painfully obvious that his play in his own zone is not acceptable if you actually watch the game.

I can guarantee, with 100% certainty, that you watched less than 2 games he played. And why are you obsessing over a minor move for a 5/6/7 dman? Yikes

 

[Menzinger]

Andrae. I don't care what some analytics dweeb with a spreadsheet comes up with, it's painfully obvious that his play in his own zone is not acceptable if you actually watch the game.

Any examples, or game clips you could actually point to?

 

[Strangle]

Sounds more like he bleeds green. That’s a hell of a lot of money for his first big contract.
And yes he’s one of you. Except for the $68 million he just got.

The leafs have money, they need a defenseman, makar would likely sign for $18m today if he was up for UFA, what’s the problem with this?

Also, is anyone concerned about how Tampa plans to replace this guy? Carlson for $10m? Andersson for $9.5m?

I don’t think Tampa should have made this deal at all

 

[Halakitlikethat]

But we will see. This will be a good thread to bring up next Christmas

Can’t wait

 

[TheKrebsCycle]

He absolutely was a journeyman until this past year.

You realize of course that a journeyman usually refers to a player that plays for many different teams right ? That isn’t Raddysh

 

[TheKrebsCycle]

not for long

They likely end up paying him for years via whatever retention makes him tradable . But good I guess ?