Funny enough, I think the guy who's really getting screwed here is...Shapiro.
-AA did the "win-now" trades, he's leaving looking good, as an Executive of the Year and all that, leaving a potato that if not hot, is about to get hotter. Shapiro is the one who'll have to deal with the consequences of AA's trades;
-The team is a little bit older; farm system is weaker
-Price is leaving, and Shapiro may have to give a terrible FA deal to some other pitcher to replace him
-The fans will hate him because he's the nasty American who "pushed out" the much-loved, Canadian, Executive of the year
-Now that they've tasted victory, the fans will no longer be satisfied with any less than what AA did - winning the AL East/making the playoffs, maybe even the World Series. This ain't Cleveland no more..(welcome to "world series or bust" world, Toronto fans)
-If AA's Lieutenants follow him out, Shapiro pretty much has to rebuild a front office
Ugh. Not a good way to start his tenure there. If I'm him, I bump up Lacava (Assistant GM) to GM, keep everybody like DD did here and increase their salaries.
Man, DD really did luck out.