Realistic Moves

If the Leafs traded Nylander (which IMO Is a mistake) they would want to improve the quality of their team for the upcoming season. They definitely don't do that here. I'm not certain they're looking for prospects or draft picks (especially draft picks two years away, where a player may not be ready for the NHL until 2027ish). I am not going to say the value is horrible, I just don't think that deal works from the Leafs perspective.

The Flyers are giving up too much for a RW that doesn't really make them much more competitive. If the Flyers are going to trade these kinds of assets it better be for Defense or Center help not another winger.

Trading for Nylander 100% makes them more competitive. They get a dynamic winger that pair with a Selke Center. As well as a better threat on the PP that desperately needs more creativity on it. A better 2C than Hayes would be great, but I dont see any center out there that would be a good fit other than Kadri, who would cost too much

yeah thats fair, The thinking is that with more cap flexibility, and more trade capital allows them to go out and get lets say a #1 goalie, while also not downgrading a ton at the winger position.

It's not terrible value-- IF the 1st, prospect are flipped for something that makes TOR better for the next 1-2 seasons, and utilizes cap space. Both moves would have to be in place for either to work.