I don't understand the correlation between Tim Thomas to the Leafs and R.A. Dickey to the Jays.
Had Tim Thomas been traded to the Leafs he would have just retired. He would never accept a deal to come play in a Socialist country.
I don't feel that sacrificing youth for the Leafs makes sense, whereas the Jays need to bottleneck their talent in order to become a competitive team. In the NHL there is parity, and therefore prospects and organizational depth play a much more important role.
In MLB there are superpower teams that have tons of money, and smaller market teams have to pick a year to "go for it" and then deal with another 5-6 year period of rebuilding.