I vehemently disagree.
A big trade would boost the team, yes, but at huge cost. Especially for the ace starter that makes the WS a "Possibilty". The truth is that no trade will single-handedly make the Jays a WS contender if they weren't already in the conversation. The A's and Tigers are both elite now in the current AL, and nothing the Jays could do will make those playoff series easier unless they transform themselves into the Dodgers overnight.
As for the 21-year bitterness, it's not AA's responsibility to make up for the failings of previous regimes. Past disappointments shouldn't dictate moves for the present or future.