Let's not forget that they lost 89 games in 2012, but I don't think they were expected to lose that many games going into the season, in fact, there was a lot of excitement about how the team was coming together at the start of the season. It's much different to go into a season being expected to lose 90+ games with a chance at 100 losses, that's just not what the Jays are about. They're about having decent teams, good enough to attract enough viewers for RSN, but not good enough to win it all. I think the mandate was to improve the team, especially the decimated starting rotation and to "not strike out" in doing so.
Remember, they were rumoured to have been in on JJ in July 2012 and maybe AA wasn't ready to give up the package the Marlins wanted. Then they reportedly struck out on Peavy and Sanchez, so I could see AA going back to the Marlins in a bad spot.
At the end of the day, I could live with the Marlins trade because of the need to improve the rotation in particular and because there's no doubt in my mind that it was decided Escobar would be off the team one way or another. The Dickey trade was just stupid, AA just accepted the rationale that there's a certain price that you have to pay for a CY winner without much of a fight and I think he even said so.
I have to admit that I picked the team to win between 86-92 games and to certainly be in contention in September....tells you how much I know.