Leafs obviously aren't a true Stanley Cup potential. With that said - they're in a situation where the coach completely lost the team last year, their difference makers are about 30, and they don't have either of their next 2 1st round DP's. This is a deal for an organization trying to do the best it can with the cards it has to play. I understand why they don't want to rebuild right now. And if the Leaf's absolutely implode this year, they can still rebuild next year. Matthews value potentially goes up with a team being able to negotiate an extension on 7/1/2027 so the acquiring team knows they're getting him long term. Knies and Nylander trade value isn't materially affected by 1 less year on those deals. If that does happen, it's not like Raddysh's contract is going to be an anchor that is a problem, or that the Leaf's moved premier assets to get DR that could be bettered used elsewhere. IMO, at the end of the day - there is potential upside and no real downside to this deal.
My point on the age is that Raddysh is just 30 with not a ton of NHL miles on the body. This isn't the case of signing Tanev to that deal he got. IMO, this is a reasonable UFA deal where you hope it's only the last couple of years that are questionable, which is the standard expectation for UFA contracts.
I would just end that from the TB games I saw - Raddysh wasn't the problem on the Lightning. They were obviously missing Hedman, and a bunch of guys underperformed. Raddysh, while solid, isn't the level of player who is going to carry a team on his back, and that shouldn't be the expectation based on his contract going forward.