Honestly, I think the 2015 trades were more justifiable (whether I agreed with them or not), but reality is those trades were simply doubling down on a franchise changing 2013 off-season. He made terrible, terrible trades in 2013. The 2015 momentarily made us forget about 2013, but the direction he was taking was simply not a sustainable process.
I've said before, AA leaving was a calculated move on his part. He leaves as a hero without having to deal with the post-2016 s*** storm, and his replacements get all the blame for things that he himself would not have been able to do (re-signing Price, fitting Bats/Edwin into a $140m payroll after 2016, etc).
I'd rather see the team be consistently good than have one or two good years before another drought. No one will give a damn about the bat flip in 2019 if the Jays miss the playoffs in 2016, 17, and 18. You have to build a consistent winner. Trading prospects for guys making $20m a year from ages 31-36 is not the way to do that, and that approach is going to catch up to the Jays after 2016. Shapiro/Atkins have done a good job of at least weathering it a bit.