Setting aside that obvious and tired trainwreck, Ryjo cannot be double retained any further. Actually, I'm not sure he can even be retained one more time, but I'd need to look it up. Definitely zero chance he can be retained on two more times.

At least Cowan is included in this one

So that's not going to happen. Simply because the Leafs have a very empty closet of assets as it is. This trade essentially takes any asset the Leafs may have of value and ships it away so they're left with basically 0. Next season when they still have Tavares at 11M they're going to need ELC to make sure they're not over the cap. .